CN1050364C - 7-糖氧基苯并吡喃衍生物及抗变应性剂 - Google Patents
7-糖氧基苯并吡喃衍生物及抗变应性剂 Download PDFInfo
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- CN1050364C CN1050364C CN95107126A CN95107126A CN1050364C CN 1050364 C CN1050364 C CN 1050364C CN 95107126 A CN95107126 A CN 95107126A CN 95107126 A CN95107126 A CN 95107126A CN 1050364 C CN1050364 C CN 1050364C
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/24—Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/075—Benzo[b]pyran-2-ones
-
- A—HUMAN NECESSITIES
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Abstract
一种由下面通式(Ⅰ)代表的7-糖氧基苯并吡喃衍生物及其生理可接受盐:
其中:R1是氢原子、酰基、烷基、环烷基、链烯基或芳烷基,R2是氢原子、烷基、环烷基、链烯基或芳烷基,R3是其羟基被保护的或未被保护的糖基,它选自葡糖基、甘露糖基和半乳糖基。
Description
本发明涉及7-糖氧基苯并吡喃衍生物,它由苯并吡喃7-位上的羟基与己糖衍生物糖基化反应而成。这些化合物或其生理上可接受盐可用作抗变应性剂。
苯并吡喃衍生物,如本发明的7-糖氧基苯并吡喃衍生物的糖苷配基部分已经被公开,例如在EP-A-0598117中由本发明人公开的,类似的苯并吡喃衍生物例如由Donald T.Witiak在.J.Med.Chem.,Vol.31,pp.1473-1445,1988上公开,在美国专利4,845,121中也已公开,但是没有关于3-或4-糖氧基苯并吡喃衍生物,例如它的7-位苷的报导,此外,对本发明的7-糖氧基苯并吡喃衍生物及其生理上可接受盐的抗变应性活性是未知的。
由于目前市售的抗变应性剂在效率、安全性及生物药效率上不令人满意,因此关于开发抗变应性剂的研究仍在广泛地进行。例如,一种常用的抗变应性剂安宁(Tranilast)(俗名)在治疗过敏疾病时需要较多的服用剂量,尽管它的鼠急性毒性值(LD50)较低(780mg/kg),因此造成在服用时需非常注意的问题,因为其有效剂量与毒性剂量非常接近,即:其安全使用范围窄。此外一种已知的平喘药色甘酸二钠(disodium Cromoglicate)(俗名),其在毒性上的效果经临床证实是令人满意的,但是它必须通过喷雾吸入使用,因为其胃肠吸收性极差。此外,这些已知的抗变应性剂对迟发型变态反应无效,而只对速发型变态反应有效。变应性病的慢性病症(包括哮喘和特异性皮炎)是一种严重的问题,迟发型变态性与慢性病症的发展尤其有关。因此,希望使用对速发型变态反应和迟发型变态反应都有效的药物作为抗变应性剂。正如一般所知的,类固醇对速发型变态反应和迟发型变态反应都有效,但是却引起严重的副作用。
正如上面所述,目前报道的大多数抗变应性剂具有各种各样的缺点,因为它们在迟发型变态反应上缺乏药效的原因而未显示出足够的治疗效果,由于它们的安全范围窄因而安全性较低,或者它们的服用方法由于较差的肠胃吸收能力而受到限制。因此,目前大多数注意力已经转向开发口服低毒对速发型变态反应及迟发型变态反应都有效的药物上。
在EP-A-0598117中,本发明的发明人已经提出了一种苯并吡喃衍生物及含有该衍生物作为活性成份的抗变应性剂。此时,已经考虑到了现有技术中的上述问题,我们打算提供一种作为具有低毒及优良效果的药物和抗变应性剂的更有用的新物质。
为了提供作为药物更有效的化合物,本发明的发明人通过用己糖衍生物糖基化它的7-位羟基而合成了EP-A-0598117中所公开的苯并吡喃衍生物的各种糖基化化合物,并试验了它们的抗变应性活性和安全性。结果,本发明人发现由下面通式(I)代表的7-糖氧基苯并吡喃衍生物显示出了明显的优良抗变应活性,并且毒性低。本发明是基于这一发现而完成的。因此,本发明涉及一种由通式(I)代表的7-糖氧基苯并吡喃衍生物:其中:R1是氢原子、酰基、烷基、环烷基、链烯基、或芳烷基,R2是氢原子、烷基、环烷基、链烯基、或芳烷基,R3是其羟基被保护的或未被保护的糖基,并选自葡糖基、甘露糖基、半乳糖基。本发明还涉及该衍生物的生理上可接受盐和含有由上面通式(I)表示的7-糖氧基苯并吡喃衍生物或其生理可接受盐作为活性成份的抗变应性剂。
首先,描述由上面通式(I)所表示的7-糖氧基苯并吡喃衍生物。
在本发明的通式(I)中,R1是氢原子、酰基、烷基、环烷基、链烯基、或芳烷基。
酰基的说明例子包括:链烷酰基如:乙酰基、丙酰基、丁酰基、异丁酰基等、芳酰基如:苯甲酰基或具有取代基的苯甲酰基(如:对甲氧基苯甲酰基、对甲基苯甲酰基、对氯苯甲酰基或对硝基苯甲酰基)等、以及酰基如烷氧基羰基(如:甲氧羰基或乙氧羰基)等,其中链烷酰基是优选的,乙酰基是特别优选的。
烷基的说明例子包括:直链或支链无环烷基,如:甲基、乙基、丙基、异丙基、正-丁基、仲-丁基、叔-丁基、正戊基、2-甲基戊基、己基、辛基、癸基、十二烷基等,优选的具有1至12个更优选1至10个碳原子的烷基。
环烷基的说明例子包括:直链或支链环烷基,例如:未取代的环烷基如:环丙基、环戊基、环己基和环辛基、用烷基取代的环烷基如:4-甲基环己基和二甲基环己基等,其中具有5至8个总的环链及支链的碳原子的环烷基是优选的,4-甲基环己基是更优选的。
链烯基的说明例子包括:直链或支链链烯基,如:乙烯基、丙烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、3-甲基-2-丁烯基、香叶基等,优选的是具有2-10个更优选具有6-10个碳原子的链烯基。
芳烷基的说明例子包括:那些用作羟基保护基的芳烷基,例如:苄基或具有一个取代基的苄基(如:对甲氧基苄基、对甲基苄基、对氯苄基或对硝基苄基)等,其中未取代的苄基是特别优选的。
在本发明的通式(I)中,R2是氢原子、烷基、环烷基、链烯基、或芳烷基。
烷基的说明例子包括:直链或支链烷基,如:甲基、乙基、丙基、异丙基、正-丁基、仲-丁基、叔-丁基、正戊基、2-甲基戊基、己基、辛基、癸基、十二烷基等,优选的是具有1至12个、更优选1至10个碳原子的烷基。
环烷基的说明例子包括:直链或支链环烷基,例如:未取代的环烷基如:环丙基、环戊基、环己基和环辛基、用烷基取代的环烷基如:4-甲基环己基和二甲基环己基等,其中具有5至8个总的环链及支链碳原子的环烷基是优选的,4-甲基环己基是更优选的。
链烯基的说明例子包括:直链或支链链烯基,如:乙烯基、丙烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、3-甲基-2-丁烯基、香叶基等,优选的是具有2-10个更优选具有6-10个碳原子的链烯基。
芳烷基的说明例子包括:那些用作羟基保护基的芳烷基,例如:苄基或具有一个取代基的苄基(如:对甲氧基苄基、对甲基苄基、对氯苄基或对硝基苄基)等,其中未取代的苄基是特别优选的。
在本发明的通式(I)中,R2是氢原子、烷基、环烷基、链烯基、或芳烷基。
烷基的说明例子包括:直链或支链烷基,如:甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-甲基戊基、己基、辛基、癸基、十二烷基等,优选的是具有1至12个更优选的1至10个碳原子的烷基。
环烷基的说明例子包括:直链或支链环烷基,例如:未取代的环烷基如:环丙基、环戊基、环己基和环辛基、用烷基取代的环烷基如:4-甲基环己基和二甲基环己基等,其中具有5至8个总的环链及支链碳原子的环烷基是优选的,4-甲基环己基是更优选的。
链烯基的说明例子包括:直链或支链链烯基,如:乙烯基、丙烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、3-甲基-2-丁烯基、香叶基等,优选的是具有2-10个更优选具有6-10个碳原子的链烯基。
芳烷基的说明例子包括:那些用作羟基保护基的芳烷基,例如:苄基或具有一个取代基的苄基(如:对甲氧基苄基、对甲基苄基、对氯苄基或对硝基苄基)等,其中未取代的苄基是特别优选的。
在通式(I)中用R3表示的糖基选自:葡糖基、甘露糖基、半乳′糖基,其所有或部分涉及糖基键的羟基可用或不用保护基保护。通常糖化物已知具有D和L立体异构体,这些也包含在本发明中。用作糖基原料的己糖衍生物是葡萄糖、甘露糖、半乳糖,其所有或部分羟基可用或不用保护基保护其中优选的是未保护的糖基。本发明的化合物,7-糖氧基苯并吡喃衍生物是这样一种化合物,其中这些己糖衍生物的任意一个是通过苷键连接到苯并吡喃衍生物的7-位上的。这些苷键可包括α-和β-键型,这两种键型包含在本发明的7-糖氧基苯并吡喃衍生物中。
关于用保护基保护的糖基,优选的保护基的例子包括那些通常用于糖化物的保护基,例如:酰基、芳烷基等。在这种情况下酰基的说明例子包括:链烷酰基如:乙酰基、丙酰基、丁酰基、异丁酰基等、芳酰基如:苯甲酰基或具有一个取代基的苯甲酰基(如:对-甲氧基苯甲酰基、对-甲基苯甲酰基、对-氯苯甲酰基或对硝基苯甲酰基)等、烷氧基羰基(如:甲氧羰基或乙氧羰基)等,其中链烷酰基是特别优选的。
芳烷基的说明例子包括:苄基或具有一个取代基的苄基(如:对甲氧基苄基、对甲基苄基、对氯苄基或对硝基苄基)等。
优选的保护基是苄基和乙酰基,其中乙酰基是特别优选的。
尽管它根据R1和R2的取代基的类型变化,但是半乳糖可用作最优选的糖基,接着顺序的是葡萄糖和甘露糖。此外,不保护的糖基比保护的相应物更优选。
从抗变应性活性看,本发明的7-糖氧基苯并吡喃衍生物的优选例子是这样一种化合物,其中R1是氢原子、烷基、环烷基或链烯基,R2是氢原子、烷基、环烷基或链烯基,R3葡糖基、甘露糖基或半乳糖基,更优选的例子是这样一种化合物,其中R1是烷基、环烷基或链烯基,R2是氢原子、R3是葡糖基、甘露糖基或半乳糖基,最优选的例子首先是这样一种化合物,其中R1是烷基、R2是氢原子,R3是萄糖基,其次是这样一种化合物,其中R1环烷基,R2是氢原子,R3葡糖基、第三是这样一种化合物,其中R1是链烯基,R2是氢原子,R3是葡糖基,第四是这样一种化合物,其中R1是烷基,R2是氢原子,R3是半乳糖基,第五是这样一种化合物,其中R1是环烷基,R2是氢原子,R3是半乳糖基,第六是这样一种化合物,其中R1是链烯基,R2是氢原子,R3是半乳糖基。
下面概述生产本发明7-糖氧基苯并吡喃衍生物的方法。
作为第一步,由本发明人的在先申请(EP-A-0598117)中公开的7-羟基苯并吡喃衍生物(1)与由通式(2)表示的己糖卤化物衍生物进行糖基化反应。各种己糖卤化物衍生物可根据已知的方法(参看L.J.Haynes和F.H.Newth,Adv.Carbohydr.,Chem.10,207(1955);W.Korytnyk和J.A.Mills,J.Chem.Soc.,1959,636)而制备。
首先,2,4-二羟基苯乙酮(a)用苄基保护,以获得化合物(b),接着如此所得的化合物的碳原子通过它的与碳酸二甲酯的反应而增加以将其转化成酮酯化合物(c)。接着它与过氧化苯甲酰反应得到化合物(d)。在这一步,用作羟基保护基的苄基通过氢化裂解而被解封,然后用酸处理而得到苯甲酰氧基化合物(e)。然后如此所得的苯甲酰氧基化合物(e)用金属醇盐在无水体系中处理以除去苯甲酰基,由此获得苯并吡喃衍生物(f)。
R1为除苯甲酰基之外的其它酰基的苯并吡喃衍生物(1)的合成如下。苯并吡喃衍生物(f)的3-位和7-位羟基先酰基化,然后7-位上的酰基被选择性地除去,由此得到7-羟基化合物。
其中4-位上用烷基、环烷基、链烯基或芳烷基取代的苯并吡喃衍生物(1)是如下合成的:将如此所得的苯并吡喃衍生物(f)(其中3-位和7-位上的羟基被保护)进行4-位上的羟基的烷基化、环烷基化、链烯基化或芳烷基化。
其中3-位上用烷基、环烷基、链烯基或芳烷基取代的苯并吡喃衍生物(1)是如此合成的:选择性地除去3-位上的酰基,接着烷基化、环烷基化、链烯基化或芳烷基化。苯并吡喃衍生物(1)可通过选择性地引入取代基而获得。
使用如此获得的苯并吡喃衍生物(1)和己糖衍生物(2),7-位上羟基的糖基化可按照已知的Koenigs-Knorr方法完成。在此糖基化中,在已知的Koenigs-knorr方法中为了加速反应可使用金属催化剂,例如:银盐,优选的是氧化银、碳酸银等。
在此反应中,使用有机溶剂作为反应溶剂。优选的溶剂例子包括醚类溶剂例如:乙醚、四氢呋喃、二甲氧基乙烷、二噁烷等,酰胺类溶剂例如:二甲基甲酰胺、二甲基乙酰胺等、腈类溶剂例如:乙腈、丙腈等。反应可在-20℃至50℃,优选的在0至30℃的温度下一般进行1至30小时。以此方法得到通式(3)的7-糖氧基苯并吡喃衍生物。
当合成在其糖基上具有未保护的羟基的化合物时,解封反应可作为第二步,通过将通式(3)的己糖部分进行脱苄基化或脱酰基化(这可按通常方法进行)而完成。即:在脱苄基化的情况下,反应可在氢气氛下通过使用金属催化剂进行氢化裂解而完成。
金属催化剂的例子包括钯和铂等催化剂,其用量为通式(3)代表的化合物的1至10%重量。在氢气中的反应可在加压条件或正常压力条件下进行。该反应通常在溶剂中进行。优选的溶剂包括醇类溶剂例如:甲醇、乙醇、丙醇、丁醇等,醚类溶剂例如:乙醚、四氢呋喃、二噁烷等和乙酸酯类溶剂例如:乙酸甲酯、乙酸乙酯、乙酸丙酯等。反应可在10至50℃,优选的在0至30℃的温度下,一般进行1至5小时。
此外,脱酰基化可通过让该化合物与作为脱酰基剂的碱反应而完成,这些碱选自氢氧化物例如:氢氧化钠、氢氧化钾、氢氧化锂等和醇盐碱例如:甲醇钠、甲醇钾、乙醇钠、乙醇钾等。
用于该反应的反应溶剂的优选例子包括低级醇例如:甲醇、乙醇、丙醇等、醚类溶剂例如:乙醚、四氢呋喃、二甲氧基乙烷、二噁烷等、酰胺类溶剂例如:二甲基甲酰胺、二甲基乙酰胺等。反应温度根据所用的反应试剂和溶剂而变化,优选在从-10至50℃,更优选从0至30℃的温度范围内。反应时间一般从1至5小时。下列化合物是如此所得的本发明7-糖氧基苯并吡喃衍生物的说明例子:3,4-二羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基(decanyloxy)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基(undecanyloxy)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-醇3-羟基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-醇3-丙酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苄基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苄氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3,4-二羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-羟基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-甲氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙氧基-4-苯甲氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-异丙氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丁氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-己氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-辛氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-癸氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-十一烷氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-环己氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(顺式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(反式-4-甲基环己氧基)-4-苄氧基-7-(四-O-苯甲基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(3-己烯氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-香叶氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3,4-二苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-(对甲氧基苄氧基)-4-苄氧基-7-(四-O-苄基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-甲氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-乙氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-异丙氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-丁氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-己氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-辛氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-癸氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-十一烷氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-环己氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(顺式-4-甲基环己氧基)-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(反式-4-甲基环己氧基)-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(3-己烯氧基)-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-香叶氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(对甲氧基苄氧基)-7-(β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-环己氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(顺式-4-甲基环己氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(反式-4-甲基环己氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-甲氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-癸氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-十一烷氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-甲氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-苯甲酰基-β-D-吡喃葡萄糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-甲氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-乙氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-异丙氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-丁氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-己氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-辛氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-癸氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-十一烷氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-环己氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(顺式-4-甲基环己氧基)-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(反式-4-甲基环己氧基)-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(3-己烯氧基)-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-香叶氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(对甲氧基苄氧基)-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-环己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(顺式-4-甲基环己氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(反式-4-甲基环己氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-甲氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-乙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-异丙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-丁氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-辛氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-癸氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-十一烷氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-香叶氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-甲氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-乙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-异丙氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-辛氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-香叶氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-苯甲酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-甲氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-乙氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-异丙氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-丁氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-己氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-辛氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-癸氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-十一烷氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-环己氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(顺式-4-甲基环己氧基)-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(反式-4-甲基环己氧基)-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(3-己烯氧基)-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-香叶氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-苄氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-羟基-4-(对甲氧基苄氧基)-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-环己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(顺式-4-甲基环己氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(反式-4-甲基环己氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-甲氧基-7-(四-O-乙酰基β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-癸氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-十一烷氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-苯甲酰氧基-4-(对甲氧基苄氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-甲氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-乙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-异丙氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-(3-己烯氧基)-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-丙酰氧基-4-香叶氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-甲氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-乙氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-异丙氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-丁氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-己氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-辛氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-癸氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-十一烷氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(3-己烯氧基)-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-香叶氧基-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮3-乙酰氧基-4-(对甲氧基苄氧基)-7-(四-O-苯甲酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮
这些化合物的生理可接受盐也包含在这些示意例子中。
在此所用的词“生理可接受盐”是指如上述化合物的无毒碱性加成盐,例如钠盐、钾盐、镁盐、钙盐、铵盐、无毒胺盐等。这些生理可接受盐可用已知方法生产,并也包含在本发明中。
由于本发明的7-糖氧基苯并吡喃衍生物及其生理可接受盐(此后称作“本发明的化合物”)如后面实施例中所描述的具有抑制速发型和延迟型变态反应的功能,因此可用作治疗或防治各种变应性疾病的抗变应性制剂。
在此所用的词“变应性疾病”是指由外在或内在抗原引起的使生物免疫机制过分激活而导致的变应性疾病,这包括速发型哮喘病、延迟型哮喘病、支气管性哮喘病、儿童哮喘病、特应性皮炎、变应性皮炎,荨麻疹、湿疹、特应性结膜炎、变应性鼻炎、枯草热、食物过敏、过敏性胃肠炎、变应性结肠炎、药物过敏、接触性皮炎、自身免疫疾病等。
包含本发明的化合物作为活性成份的抗变应性剂可口服或肠胃外使用(例如:静脉注射、皮下注射、经皮吸收、直肠用药等)。这样的药剂根据各种用途可制成各种剂型,例如:片剂、胶囊、颗粒剂、细subtilase、粉剂、锭剂、舌下用(subringual)片剂、栓剂、膏剂、注射液、乳液、悬浮液、药物糖浆等。这些剂型可根据已知的技术制备,并使用这类药物通常所用的药物可接受载体,例如:赋形剂、粘合剂、崩解剂、润滑剂、保存剂、抗氧剂、等渗剂、缓冲剂、涂复剂、甜味剂、溶剂、基质、分散剂、稳定剂、着色剂等。
这些药物可接受载体的示意例子列于下面。
首先,作为赋形剂可以列出如下:淀粉和淀粉衍生物(例如:糊精、羧甲基淀粉等)、纤维素和纤维素衍生物(例如:甲基纤维素、羟丙基甲基纤维素等)、糖(例如:乳糖、蔗糖、葡萄糖等)、硅酸和硅酸盐(例如:天然存在的硅酸铝、硅酸镁等)、碳酸盐(例如:碳酸钙、碳酸镁、碳酸氢钠等)、氢氧化铝镁、合成的水滑石、聚氧乙烯衍生物、单硬脂酸甘油酯、脱水山梨糖醇单油酸酯等。
作为粘合剂可以列出如下:淀粉和淀粉衍生物(例如:α-淀粉、糊精等)、纤维素和纤维素衍生物(例如:乙基纤维素、羧甲基纤维素钠、羟丙基甲基纤维素等)、阿拉伯树胶、黄蓍胶(trag-anth)、明胶、糖(例如:蔗糖、葡萄糖等)、乙醇、聚乙烯醇等。
作为崩解剂可以列出如下:淀粉和淀粉衍生物(羧甲基淀粉、羟丙基淀粉等)、纤维素和纤维素衍生物(例如:羧甲基纤维素钠、结晶纤维素、羟丙基甲基纤维素等)、碳酸盐(例如:碳酸钙、碳酸氢钙等),黄蓍胶、明胶、琼脂等。
作为润滑剂可以列出如下:硬脂酸、硬脂酸钙、硬脂酸镁、滑石、硅酸和其盐(例如:轻质硅酸酐、天然存在的硅酸铝等)氧化钛、磷酸氢钙、无水氢氧化铝凝胶、大粒凝胶(macrogol)等。
作为保存剂可以列出如下:对羟基苯甲酸酯、亚硫酸盐(例如:亚硫酸钠、焦亚硫酸钙等)、磷酸盐(例如:磷酸钠、聚磷酸钙、聚磷酸钠、甲基磷酸钠等)、醇(例如:氯丁醇、苯甲醇等)、氯苄烷铵(bemzalkonium Chloride)、氯苄乙铵(benzethonium Chloride)、酚、甲酚、氯甲酚、二氢乙酸(dihydroacetic acid)、二氢乙酸钠(dihydroacetate)、甘油山梨酸、糖等。
作为抗氧剂可以列出如下:亚硫酸盐(例如:亚硫酸钠、亚硫酸氢钠等)、雕白粉、异抗坏血酸(erythorbic)、L-抗坏血酸、半胱氨酸、硫甘油、丁基羟基茴香醚、二丁基羟基甲苯、丙基没食子酸、棕榈酸抗坏血酸酯、dl-α-生育酚等。
作为等渗剂可以列出如下:氯化钠、硝酸钠、硝酸钾、糊精、甘油、葡萄糖等。
作为缓冲剂可以列出如下:碳酸钠、盐酸、硼酸、磷酸盐(例如:磷酸氢钠)等。
作为涂复剂可以列出如下:纤维素衍生物(例如:羟丙基纤维素、纤维素乙酸酯邻苯二甲酸酯、羟丙基甲基纤维素邻苯二甲酸酯等)、紫胶、聚乙烯基吡咯烷酮、聚乙烯基吡啶(例如:聚-2-乙烯基吡啶、聚-2-乙烯基-5-乙基吡啶等)聚乙烯基乙酰基二乙氨基乙酸酯、聚乙烯醇邻苯二甲酸酯、甲基丙烯酸酯、甲基丙烯酸酯共聚物等。
作为甜味剂可以列出如下:糖(葡萄糖、蔗糖、乳糖等)、糖精钠、糖醇等。
作为溶剂可以列出如下:乙二胺、烟酰胺、糖精钠、柠檬酸、柠檬酸酯、苯甲酸钠、皂类、聚乙烯基吡咯烷酮、多溶剂化物(polysolvates)、脱水山梨糖醇脂肪酸酯、甘油、丙二醇、苯甲醇等。
作为基质可以列出如下:脂肪(例如:猪脂等)、植物油(例如:橄榄油、芝麻油等)、动物油、羊毛脂酸、凡士林、石蜡、蜡、树脂、膨润土、甘油、乙二醇油、高级醇(例如:硬脂醇、鲸蜡醇)等。
作为分散剂可以列出如下:阿拉伯树胶、黄蓍胶、纤维素衍生物(例如:甲基纤维素等)、硬脂酸多酯、山梨糖醇倍半油酸酯、单硬脂酸铝、藻酸钠、多溶剂化物、山梨糖醇脂肪酸酯等。
最后,作为稳定剂可以列出如下:亚硫酸盐(例如:亚硫酸氢钠等)、氮气、二氧化碳等。
尽管本发明的化合物在这些药物制剂中的量取决于剂型,但是优选的含量为浓度0.01至100%重量。
本发明的抗变应性制剂的剂量可根据要治疗的每个哺乳动物(例如:人、小鼠、大鼠、猪等)的各种病的程度及医嘱在较宽的范围内变化。但是,通常在口服的情况下可以用每天每公斤体重从0.01-200mg,优选0.01-50mg,最好0.05-10mg的活性成分剂量服用,或者在肠胃外使用的情况下以每天每公斤体重从0.01-10mg,优选0.01-5mg的活性成分剂量。上述的日剂量可一次使用或分次使用,并可根据病情和医嘱改变。
下面这些例子是用来举例说明本发明的化合物和这些化合物的医药组合物的制备,但这些例子只是用来说明本发明,而不是对本发明范围的限制。参考例1
3-甲氧基-4-苄氧基-7-乙酰氧基-2H-1-苯并吡喃-2-酮
在氩气环境下将4.61克碳酸钠(33.4毫摩尔)添加到8.11g3-甲氧基-4-羟基-7-乙酰氧基-2H-1-苯并吡喃-2-酮(27.8毫摩尔),和5.71g苄基溴(33.4毫摩尔)在50毫升DMF中的混合物中,然后该混合物在50℃搅拌2小时。反应混合物中的固体被滤出,滤液倒入200毫升水中,用500毫升苯萃取。有机层在用硫酸镁干燥后在真空中浓缩,得到油状残余物。该残余物用硅胶柱色谱法提纯(洗脱液:苯/乙酸乙酯=7/3),得到3.50克标题化合物。(产率=33%)。1H-NMR(CDCl3,δ-TMS):7.67(d,1H,J=8.8Hz),7.40(m,5H),6.82(d,1H,J=8.8Hz),6.78(s,1H),5.45(s,2H),3.85(s,3H),2.32(s,3H)IR(KBr,cm-1):1760,1720,1620,1435,1360,1220元素分析,C19H16O6计算值(%):C 67.05;H 4.75;O 28.20测定值(%):C 67.15;H 4.63;O 28.22参考例2
3-甲氧基-7-羟基-4-苄氧基-2H-1-苯并吡喃-2-酮
将0.58克甲醇钠(10.7毫摩尔)添加到3.64g 3-甲氧基-4-苄氧基-7-乙酰氧基-2H-1-苯并吡喃-2-酮(10.7毫摩尔)在50毫升甲醇中的混合物中,然后该反应混合物在室温搅拌1小时。然后加入2.31克Amberlyst-15(商标:Organocorp.),该混合物在室温搅拌1小时。Amberlyst-15被滤掉,滤液在减压下浓缩,在浓缩过程中得到沉淀物,过滤得到2.59克标题化合物。(产率=77%)1H-NMR(DMSO-d6,δ-TMS):9.30(bs,1H),7.67(d,1H,J=8.8Hz),7.40(m,5H),6.72(d,1H,J=8.8Hz),6.78(s,1H),5.45(s,2H),3.78(s,3H)IR(KBr,cm-1):3200,1760,1720,1620,1435,1360,1220元素分析,C17H14O5计算值(%):C 68.45;H 4.73;O 26.82测定值(%):C 68.25;H 4.73;O 27.02参考例3
3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮
将2.26克甲醇钠(49.20毫摩尔)添加到17.31g 4-丁氧基-3,7-二乙酰氧基-2H-1-苯并吡喃-2-酮(51.79毫摩尔),在170毫升甲醇中的混合物中,然后该反应混合物在室温搅拌3小时。然后加入22.36克Amberlyst-15,该混合物在室温搅拌1小时。滤出Amberly-st-15,滤液在减压下浓缩,得到结晶产物,该产物从四氢呋喃和己烷中再沉淀得到12.87克标题化合物。(产率=85%)1H-NMR(DMSO-d6,δ-TMS):10.60(s,1H),7.64(d,1H,J=8.8Hz),6.87(dd,1H,J=2.4Hz,J=8.8Hz),6.75(d,1H,J=2.4Hz),4.42(t,2H,J=6.2Hz),2.33(s,3H),1.80~1.70(m,2H),1.55~1.40(m,2H),0.94(t,3H,J=7.4Hz)IR(KBr,cm-1):3200,2950,1760,1690,1620,1410,1340元素分析,C15H16O6计算值(%):C 61.64;H 5.52;O 32.84测定值(%):C 61.60;H 5.53;O 32.87参考例4
3-乙酰氧基-4-己氧基-7-羟基-2H-1-苯并吡喃-2-酮
按照参考例3,用30.00克4-己氧基-3,7-二乙酰氧基-2H-1-苯并吡喃-2-酮(82.79毫摩尔)代替4-丁氧基-3,7-二乙酰氧基-2H-1-苯并吡喃-2-酮,得到22.01克标题化合物。(产率=83%)1H-NMR(DMSO-d6,δ-TMS):10.63(s,1H),7.63(d,1H,J=8.8Hz),6.86(dd,1H,J=2.4Hz,J=8.8Hz),6.74(d,1H,J=2.4Hz),4.41(t,2H,J=6.2Hz),2.32(s,3H),1.80~1.70(m,2H),1.50~1.25(m,4H),0.87(t,3H,J=7.2Hz)IR(KBr,cm-1):3200,2930,1760,1690,1620,1410,1340元素分析,C17H20O6计算值(%):C 63.74;H 6.29;O 29.97测定值(%):C 63.76;H 6.26;O 29.98参考例5
3-乙酰氧基-4-辛氧基-7-羟基-2H-1-苯并吡喃-2-酮
按参考例3,用30.00克4-辛氧基-3,7-二乙酰氧基-2H-1-苯并吡喃-2-酮(76.84毫摩尔)代替4-丁氧基-3,7-二乙酰氧基-2H-1-苯并吡喃-2-酮,得到23.19克标题化合物。(产率=87%)1H-NMR(DMSO-d6,δ-TMS):10.62(s,1H),7.63(d,1H,J=8.8Hz),6.86(dd,1H,J=2.4Hz,J=8.8Hz),6.74(d,1H,J=2.4Hz),4.46(t,2H,J=6.4Hz),2.32(s,3H),1.80~1.65(m,2H),1.50~1.10(m,6H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3200,2900,1760,1690,1620,1410,1340元素分析,C19H24O6计算值(%):C 65.50;H 6.94;O 27.55测定值(%):C 65.38;H 6.98;O 27.64实施例1
3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-苯并吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物1)
在氩气环境下,在室温将1.53克3-甲氧基-4-苄氧基-7-羟基-2H-1-苯并吡喃-2-酮(5.12毫摩尔)和4.21克2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖基溴(10.23毫摩尔)溶解在20毫升乙腈中,将1.19克氧化银(I)(5.12毫摩尔)和13.77克4A分子筛(Merck)加入到该溶液中,该混合物在室温搅拌2小时。过滤后,滤液在减压下浓缩,得到油状残余物。该残余物用硅胶柱色谱法提纯(洗脱液:苯/乙酸乙酯=2/1),得到1.77克标题化合物(1)。(产率=55%)1H-NMR(CDCl3,δ-TMS):7.70(d,1H,J=8.8Hz),7.20~7.40(m,5H),6.88(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H),5.25~5.35(m,2H),5.14(t,1H,J=8.0Hz),4.93(d,1H,J=8.0Hz),4.21~4.28(m,2H),3.82~3.85(m,1H),3.78(s,3H),2.02~2.22(m,12H)IR(KBr,cm-1):1750,1620,1435,1360,1240元素分析,C31H32O14计算值(%):C 59.23;H 5.09;O 35.68测定值(%):C 59.40;H 4.95;O 35.65实施例2
3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物2)
在氢气环境下,在室温将2.19克3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(3.84毫摩尔)和0.22克10%的披钯活性碳在20毫升乙酸乙酯中的混合物搅拌2小时。滤出催化剂,将滤液蒸发得到粗产物。用乙醚洗涤粗产物后,得到1.59克标题化合物(1)。(产率=85%)1H-NMR(CDCl3,δ-TMS):10.50(bs,1H),7.70(d,1H,J=8.8Hz),6.88(d,1H,J=8.8Hz),6.78(s,1H),5.25~5.35(m,2H),5.14(t,1H,J=8.0Hz),4.93(d,1H,J=8.0Hz),4.21~4.28(m,2H),3.82~3.85(m,1H),3.78(s,3H),2.02~2.22(m,12H)IR(KBr,cm-1);3250,1750,1620,1435,1360,1240元素分析,C24H26O14计算值(%):C 53.53;H 4.83;O 41.64测定值(%):C 53.40;H 4.90;O 41.70实施例3
3-甲氧基-4-羟基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物3)
在5℃下,在氩气环境中将0.15克甲醇钠添加到0.58克3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(1.07毫摩尔)在12毫升甲醇的混合物中,然后该反应混合物在室温搅拌1小时。然后加入0.75克Amberlyst-15,该混合物在室温搅拌1小时。在通过添加过量甲醇的中和过程中产生的沉淀物溶解后,滤出Amberlyst-15,滤液在真空中浓缩,得到沉淀物,过滤得到0.31克标题化合物(3)。(产率=77%)1H-NMR(DMSO-d6,δ-TMS):11.40(bs,1H),7.67(d,1H,J=8.4Hz),6.95(s,1H),6.94(d,1H,J=8.4Hz),4.98(bs,4H),4.83(d,1H,J=7.6Hz),3.85(s,3H),3.65(d,1H,J=7.6Hz),3.51(d,1H,J=7.6Hz),3.41(m,1H),3.31~3.20(m,3H)IR(KBr,cm-1):3350,1660,1630,1580,1270元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.52;H 4.85;O 43.63实施例4
3-甲氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(化合物4)
按照实施例1,用4.21克2,3,4,6-四-O-乙酰基-β-D-吡喃甘露糖基溴(10.23毫摩尔)替代2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖基溴,得到1.88克标题化合物(4)。(产率=58%)1H-NMR(CDCl3,δ-TMS)7.67(d,1H,J=8.4Hz),7.20~7.40(m,5H),6.95(s,1H),6.94(d,1H,J=8.4Hz),6.00(s,1H),5.55(m,2H),5.45(s,2H),5.40(m,1H),4.23(m,2H),4.15(s,1H),3.75(s,3H),2.02~2.22(m,12H)IR(KBr,cm-1):1750,1620,1435,1360,1240元素分析,C31H32O14计算值(%):C 59.23;H 5.09;O 35.68测定值(%):C 59.40;H 5.15;O 35.45实施例5
3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物5)
按照实施例1,用4.21克2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基溴(10.23毫摩尔)替代2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖基溴,得到1.82克标题化合物(5)。(产率=56%)1H-NMR(CDCl3,δ-TMS):7.72(d,1H,J=8.8Hz),7.20~7.40(m,5H),6.88(d,1H,J=8.8Hz),6.78(s,1H),6.01(s,1H),5.55(m,2H),5.45(s,2H),5.40(s,1H),5.16~5.25(m,1H),4.10~4.20(m,2H),3.90(s,3H),2.02~2.22(m,12H)IR(KBr,cm-1):1750,1620,1435,1360,1240元素分析,C31H32O14计算值(%):C 59.23;H 5.09;O 35.68测定值(%):C 59.42;H 5.15;O 35.43实施例6
3-甲氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(化合物6)
按实施例2,用3-甲氧基-4-苄氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮替代3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮,得到0.321克标题化合物(6)。(产率=81%)1H-NMR(DMSO-d6,δ-TMS):11.40(bs,1H),7.67(d,1H,J=8.4Hz),6.95(s,1H),6.94(d,1H,J=8.4Hz),6.00(s,1H),5.55(m,2H),5.40(m,1H),4.23(m,2H),4.15(s,1H),3.75(s,3H),2.02~2.22(m,12H)IR(KBr,cm-1):3350,1660,1630,1580,1270元素分析,C24H26O14计算值(%):C 53.53;H 4.83;O 41.64测定值(%):C 53.42;H 4.55;O 42.03实施例7
3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物7)
按实施例2,用3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮替代3-甲氧基-4-苄氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮,得到0.309克标题化合物(7)。(产率=78%)1H-NMR(DMSO-d6,δ-TMS):11.40(bs,1H),7.67(d,1H,J=8.4Hz),6.95(s,1H),6.94(d,1H,J=8.4Hz),4.85(d,1H,J=7.6Hz),3.85(s,3H),3.65(d,1H,J=7.6Hz),3.51(d,1H,J=7.6Hz),3.41(m,1H),3.20~3.40(m,3H),2.05~2.22(m,12H)IR(KBr,cm-1):3350,1660,1630,1580,1270元素分析,C24H26O14计算值(%):C 53.53;H 4.83;O 41.64测定值(%):C 53.42;H 4.55;O 42.03实施例8
3-甲氧基-4-羟基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(化合物8)
按实施例3,用3-甲氧基-4-羟基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮替代3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮,得到0.310克标题化合物(8)。(产率=78%)1H-NMR(DMSO-d6,δ-TMS):11.40(bs,1H),7.67(d,1H,J=8.4Hz),6.95(s,1H),6.94(d,1H,J=8.4Hz),6.00(s,1H),5.55(m,2H),5.40(m,1H),4.98(bs,4H),4.23(m,2H),4.15(s,1H),3.75(s,3H)IR(KBr,cm-1):3350,1660,1630,1580,1270元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.52;H 4.85;O 43.63实施例9
3-甲氧基-4-羟基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物9)
按实施例3,用3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮替代3-甲氧基-4-羟基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮,得到0.295克标题化合物(9)。(产率=74%)1H-NMR(DMSO-d6,δ-TMS):11.25(bs,1H),7.67(d,1H,J=8.4Hz),6.95(s,1H),6.94(d,1H,J=8.4Hz),5.00(bs,4H),4.85(d,1H,J=7.6Hz),3.85(s,3H),3.65(d,1H,J=7.6Hz),3.51(d,1H,J=7.6Hz),3.41(m,1H),3.20~3.40(m,3H)IR(KBr,cm-1):3350,1660,1630,1580,1270元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.65;H 4.85;O 43.50实施例10
3-乙酰氧基-4-苄氧基-7-(四-O-苄基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物10)
按照实施例1,用1.00克3-乙酰氧基-4-苄氧基-7-羟基-2H-1-苯并吡喃-2-酮(3.06毫摩尔)和2.70克2,3,4,6-四-O-苄基-α-D-吡喃葡糖基溴(4.43毫摩尔)替代3-甲氧基-4-苄氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖基溴,得到1.52克标题化合物(10)。(产率=58%)1H-NMR(DMSO-d6,δ-TMS):7.67(d,1H,J=8.8Hz),7.15~7.60(m,25H),6.88(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H),5.25~5.35(m,2H),5.20(m,8H),5.14(t,1H,J=8.0Hz),4.93(d,1H,J=8.0Hz),4.21~4.28(m,2H),3.82~3.85(m,1H),2.38(s,3H)IR(KBr,cm-1):1760,1640,1600,1450,1380元素分析,C52H48O11计算值(%):C 73.58;H 5.66;O 20.76测定值(%):C 73.53;H 5.78;O 20.69实施例11
3-乙酰氧基-4-羟基-7-(-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物11)
在氩气环境下,在室温将1.50克3-乙酰氧基-4-苄氧基-7-(四-O-苄氧基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(1.77毫摩尔)溶解在150毫升四氢呋喃中,添加0.15克10%的披钯活性碳,在用氢气替代氩气之后,该反应混合物在室温搅拌2小时。滤出催化剂,将滤液蒸发而得到结晶产物。用四氢呋喃和己烷再沉淀后,得到0.662克标题化合物(11)。(产率=94%)1H-NMR(DMSO-d6,δ-TMS):10.5(bs,1H),7.70(d,1H,J=8.4Hz),6.70~6.90(m,2H),5.80(bs,1H),5.32(d,1H,J=7.2Hz),5.19(s,1H),5.02(s,1H),4.50(s,1H),3.10~3.70(m,6H),2.33(s,3H)IR(KBr,cm-1):3400,1780,1670,1610,1580,1270元素分析,C17H18O11计算值(%):C 51.26;H 4.52;O 44.22测定值(%):C 51.27;H 4.51;O 44.22实施例12
3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物12)
在氩气环境下,在室温将11.74克3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮(40.18毫摩尔)和24.74克和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴(60.27毫摩尔)溶解在360毫升乙腈中。添加11.17克氧化银(I)(48.21毫摩尔)和106克4A分子筛到该溶液中,该反应混合物在室温搅拌4小时,过滤之后,滤液在减压下浓缩,得到油状残余物,该残余物用硅胶柱色谱法(洗脱液:己烷/乙酸乙酯=2/1)纯化,得到13.00克标题化合物(12)。(产率=52%)1H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.20~5.30(m,2H),4.52(t,1H,J=6.6Hz),4.46(t,2H,J=6.0Hz),4.11(d,2H,J=6.0Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.96(s,3H),1.70~1.80(m,2H),1.40~1.55(m,2H),0.93(t,3H,J=3.6Hz)IR(KBr,cm-1):2950,1750,1630,1370,1240元素分析,C29H34O15计算值(%):C 55.95;H 5.50;O 38.55测定值(%):C 55.84;H 5.58;O 38.58实施例13
3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物13)
按实施例12,用12.86克3-乙酰氧基-4-己氧基-7-羟基-2H-1-苯并吡喃-2-酮(40.18毫摩尔)和24.78克2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖基溴(60.27毫摩尔)替代3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴,得到13.58克标题化合物(13)。(产率=52%)1H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.45(t,2H,J=6.0Hz),4.10~4.40(m,3H),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),1.70~1.80(m,2H),1.25~1.50(m,6H),0.88(t,3H,J=7.2Hz)IR(KBr,cm-1):2950,1750,1620,1370,1240元素分析,C31H38O15计算值(%):C 58.13;H 4.41:O 37.47测定值(%):C 58.20;H 4.45;O 37.35实施例14
3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(化合物14)
按照实施例12,用6.00克3-乙酰氧基-4-己氧基-7-羟基-2H-1-苯并吡喃-2-酮(18.73毫摩尔)和11.55克2,3,4,6-四-O-乙酰基-β-D-吡喃甘露糖氧基溴(28.10毫摩尔)替代3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴,得到3.66克标题化合物(14)。(产率=30%)1H-NMR(DMSO-d6,δ-TMS):7.78(d,1H,J=8.8Hz),7.15~7.30(m,2H),5.94(s,1H),5.35~5.45(m,2H),5.13(t,1H,J=10.0Hz),4.45(t,2H,J=5.9Hz),3.90~4.20(m,3H),2.34(s,3H),2.18(s,3H),2.05(s,3H),2.00(s,3H),1.92(s,3H),1.70~1.80(m,2H),1.25~1.50(m,6H),0.88(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,1750,1630,1370,1240元素分析,C31H38O15计算值(%):C 58.13;H 4.41;O 37.47测定值(%):C 58.19;H 4.39;O 37.42实施例15
3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物15)
按照实施例12,用4.50克3-乙酰氧基-4-己氧基-7-羟基-2H-1-苯并吡喃-2-酮(14.05毫摩尔)和8.66克2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴(21.07毫摩尔)替代3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴,得到4.66克标题化合物(15)。(产率=51%)1H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=9.2Hz),7.05~7.15(m,2H),5.66(d,1H,J=7.2Hz),5.20~5.40(m,2H),4.50~4.55(m,3H),4.45(t,2H,J=6.2Hz),4.12(t,2H,J=6.4Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.03(s,3H),1.97(s,3H),1.70~1.80(m,2H),1.25~1.50(m,6H),0.88(t,3H,J=7.2Hz)IR(KBr,cm-1):2930,1750,1620,1370,1230元素分析,C31H38O15计算值(%):C 58.13;H 4.41;O 37.47测定值(%):C 58.16;H 4.45;O 37.39实施例16
3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物16)
按照实施例12,用14.00克3-乙酰氧基-4-辛氧基-7-羟基-2H-1-苯并吡喃-2-酮(40.28毫摩尔)和24.84克2,3,4,6-四-O-乙酰基-α-D-吡喃葡糖氧基溴(60.41毫摩尔)替代3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴,得到13.65克标题化合物(16)。(产率=50%)1H-NMR(DMSO-d6,δ-TMS):7.76(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.10~5.15(m,1H),5.04(t,1H,J=9.8Hz),4.45(t,2H,J=6.0Hz),4.05-4.35(m,3H)2.34(s,3H),2.00~2.05(m,9H),1.99(s,3H),1.70~1.80(m,2H),1.20~1.50(m,10H),0.85(t,3H,J=7.0Hz)IR(KBr,cm-1):2920,1740,1630,1610,1370,1230元素分析,C33H42O15计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.16;H 6.19;O 35.65实施例17
3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物17)
按照实施例12,用14.00克3-乙酰氧基-4-辛氧基-7-羟基-2H-1-苯并吡喃-2-酮(40.28毫摩尔)和24.84克2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴(60.41毫摩尔)替代3-乙酰氧基-4-丁氧基-7-羟基-2H-1-苯并吡喃-2-酮和2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖氧基溴,得到14.47克标题化合物(17)。(产率=53%)1H-NMR(DMSO-d6,δ-TMS):7.76(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.04(dd,1H,J=2.2Hz,J=9.0Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=7.2Hz),5.20~5.40(m,2H),4.42(t,1H, J=6.4Hz),4.45(t,2H,J=6.4Hz),4.11(d,2H,J=6.0Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.03(s,3H),1.97(s,3H),1.70~1.80(m,2H),1.20~1.50(m,10H),0.85(t,3H,J=7.0Hz)IR(KBr,cm-1):2930,1750,1620,1370,1230元素分析,C33H42O15计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.51;H 6.29;O 35.20实施例18
3-羟基-4-丁氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物18)
在5℃,在氩气环境下将3.31克甲醇钠(61.26毫摩尔)添加到19.07克3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(30.63毫摩尔)在380毫升甲醇中的混合物中,接着将该反应混合物在室温搅拌1小时。然后加入27.85克Amberlyst-15,并将混合物在室温搅拌1小时。滤出Amberlyst-15,将滤液蒸发得到结晶产物,在用乙醇再沉淀后,得到10.18克标题化合物(18)。(产率=81%)1H-NMR(DMSO-d6,δ-TMS):9.18(s,1H),7.61(d,1H,J=8.8Hz),7.00~7.10(m,2H),5.20(d,1H,J=5.6Hz),4.91(d,1.H,J=8.0Hz),4.88(d,1H,J=5.2Hz),4.67(t,1H,J=5.2Hz),4.52(d,1H,J=4.4Hz),4.48(t,2H,J=6.4Hz),3.40~3.75(m,6H),1.65~1.75(m,2H),1.40~1.50(m,2H),0.93(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2950,2930,2860,1680,1640,1610,1250元素分析,C19H24O10计算值(%):C 55.34;H 5.87;O 38.80测定值(%):C 55.41;H 5.81;O 38.78实施例19
3-羟基-4-己氧基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物19)
按照实施例18,用10.94克3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(16.81毫摩尔)替代3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮,得到6.66克标题化合物(19)。(产率=90%)1H-NMR(DMSO-d6,δ-TMS):9.19(bs,1H),7.61(d,1H,J=8.8Hz),7.00~7.10(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.47(t,2H,J=6.2Hz),3.10~3.75(m,6H),1.65~1.80(m,2H),1.20~1.50(m,6H),0.87(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2950,2920,2850,1700,1640,1610,1260元素分析,C21H28O10计算值(%):C 57.27;H 6.41;O 36.33测定值(%):C 55.25;H 6.49;O 38.46实施例20
3-羟基-4-己氧基-7-(α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(化合物20)
按照实施例18,用13.40克3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-α-D-吡喃甘露糖氧基)-2H-1-苯并吡喃-2-酮(20.60毫摩尔)替代3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮,得到7.62克标题化合物(20)。(产率=84%)1H-NMR(DMSO-d6,δ-TMS):9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1.H),4.47(t,2H,J=6.4Hz),3.85(s,1H),3.20~3.75(m,6H),1.65~1.80(m,2H),1.20~1.50(m,6H),0.87(t,3H,J=7.2Hz)IR(KBr,cm-1)3350,2950,2920,2850 1690,1630,1610,1250元素分析,C21H28O10计算值(%):C 57.27;H 6.41;O 36.33测定值(%):C 57.38;H 6.40;O 36.22实施例21
3-羟基-4-己氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物21)
按照实施例18,用12.57克3-乙酰氧基-4-己氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(19.32毫摩尔)替代3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮,得到7.55克标题化合物(21)。(产率=89%)1H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.00~7.10(m,2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.47(t,2H,J=6.6Hz),3.25~3.65(m,6H),1.70~1.80(m,2H),1.20~1.50(m,6H),0.87(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2950,2920,2850,1690,1630,1610,1250元素分析,C21H28O10计算值(%):C 57.27;H 6.41;O 36.33测定值(%):C 57.16;H 6.46;O 36.38实施例22
3-羟基-4-辛氧基-7-(β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(化合物22)
按照实施例18,用10.95克3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃葡糖氧基)-2H-1-苯并吡喃-2-酮(16.13毫摩尔)替代3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮,得到6.95克标题化合物(22)。(产率=92%)1H-NMR(DMSO-d6,δ-TMS):9.19(bs,1H),7.60(d,1H,J=8.8Hz),7.00~7.10(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.95(d,1H,J=7.2Hz),4.59(bs,1H),4.46(t,2H,J=6.4Hz),3.10~3.75(m,6H),1.65~1.80(m,2H),1.15~1.50(m,10H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3350,2920,2850,1700,1640,1610,1250元素分析,C23H32O10计算值(%):C 58.97;H 6.88;O 34.15测定值(%):C 58.92;H 6.87;O 34.21实施例23
3-羟基-4-辛氧基-7-(β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(化合物23)
按照实施例18,用20.67克3-乙酰氧基-4-辛氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮(30.46毫摩尔)替代3-乙酰氧基-4-丁氧基-7-(四-O-乙酰基-β-D-吡喃半乳糖氧基)-2H-1-苯并吡喃-2-酮,得到12.47克标题化合物(23)。(产率=87%)1H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.60(d,1H,J=8.4Hz)7.00~7.10(m,2H),5.21(bs,1H),4.91(d,1H,J=8.0Hz),4.88(bs,1H),4.66(bs,1H),4.52(d,1HJ=3.6Hz),4.47(t,2H,J=6.6Hz),3.10~3.75(m,6H),1.65~1.80(m,2H),1.15~1.50(m,10H),0.85(t,3H,J=6.6Hz)IR(KBr,cm-1):3400,2910,2850,1680,1630,1610,1250元素分析,C23H32O10计算值(%):C 58.97;H 6.88;O 34.15测定值(%):C 58.99;H 6.92;O 34.09实施例24-160
下表中列出了通过实施例所描述的方法所获得的7-吡喃糖氧基苯并吡喃衍生物(24)~(160)。
该表中所用缩写的含义如下:Glc是吡喃葡糖基;Man是吡喃甘露糖基;Gal是吡喃半乳糖基;R4是糖的保护基。
表1实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)24 24 1 CH3 苄基 Glc(β-D式) 苄基 5225 25 1 C4H9 苄基 Glc(″) 苄基 6026 26 1 C6H13 苄基 Glc(″) 乙酰基 5127 27 1 C8H17 苄基 Glc(″) 乙酰基 5328 28 1 C10H21 苄基 Glc(″) 乙酰基 5129 29 1 C12H25 苄基 Glc(″) 乙酰基 5830 30 1 (CH3)2CH 苄基 Glc(″) 乙酰基 5931 31 1 4-甲基环己基 苄基 Glc(″) 乙酰基 5032 32 1 乙烯基 苄基 Glc(″) 乙酰基 5333 33 1 3-己烯基 苄基 Glc(″) 乙酰基 5734 34 1 香叶基 苄基 Glc(″) 乙酰基 5435 35 1 C8H17 苄基 Glc(″) 苄基 5736 36 1 苄基 苄基 Glc(″) 苄基 5237 37 3 C4H9 H Glc(″) H 8338 38 3 C6H13 H Glc(″) H 8239 39 3 C8H17 H Glc(″) H 8640 40 3 C10H21 H Glc(″) H 7441 41 3 C12H25 H Glc(″) H 8342 42 3 (CH3)2CH H Glc(″) H 8843 43 3 4-甲基环己基 H Glc(″) H 8144 44 3 乙烯基 H Glc(″) H 85
表1(续)实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)45 45 3 3-己烯基 H Glc(″) H 8646 46 3 香叶基 H Glc(″) H 8347 47 3 苄基 H Glc(″) H 8748 48 4 CH3 苄基 Man(α-D式) 苄基 5349 49 4 C4H9 苄基 Man(″) 苄基 5150 50 4 C6H13 苄基 Man(″) 乙酰基 5451 51 4 C8H17 苄基 Man(″) 乙酰基 5652 52 4 C10H21 苄基 Man(″) 乙酰基 5953 53 4 C12H25 苄基 Man(″) 乙酰基 5554 54 4 (CH3)2CH 苄基 Man(″) 乙酰基 5555 55 4 4-甲基环己基 苄基 Man(″) 乙酰基 5356 56 4 乙烯基 苄基 Man(″) 乙酰基 5557 57 4 3-己烯基 苄基 Man(″) 乙酰基 5958 58 4 香叶基 苄基 Man(″) 乙酰基 5759 59 4 C8H17 苄基 Man(″) 苄基 5060 60 4 苄基 苄基 Man(″) 苄基 5061 61 6 H H Man(″) H 8962 62 6 C4H9 H Man(″) H 8063 63 6 C6H13 H Man(″) H 7964 64 6 C8H17 H Man(″) H 8665 65 6 C10H21 H Man(″) H 7966 66 6 C12H25 H Man(″) H 8067 67 6 (CH3)2CH H Man(″) H 7968 68 6 4-甲基环己基 H Man(″) H 8169 69 6 乙烯基 H Man(″) H 79
表1(续)实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)70 70 6 3-己烯基 H Man(″) H 8971 71 6 香叶基 H Man(″) H 8072 72 6 苄基 H Man(″) H 9073 73 7 CH3 苄基 Gal(β-D式) 苄基 5874 74 7 C4H9 苄基 Gal(″) 苄基 6075 75 7 C6H13 苄基 Gal(″) 乙酰基 5776 76 7 C8H17 苄基 Gal(″) 乙酰基 5877 77 7 C10H21 苄基 Gal(″) 乙酰基 5878 78 7 C12H25 苄基 Gal(″) 乙酰基 5579 79 7 (CH3)2CH 苄基 Gal(″) 乙酰基 5980 80 7 4-甲基环己基 苄基 Gal(″) 乙酰基 5781 81 7 乙烯基 苄基 Gal(″) 乙酰基 6082 82 7 3-己烯基 苄基 Gal(″) 乙酰基 5883 83 7 香叶基 苄基 Gal(″) 乙酰基 6084 84 7 C8H17 苄基 Gal(″) 苄基 5985 85 7 苄基 苄基 Gal(″) 苄基 5986 86 9 C4H9 H Gal(″) H 8687 87 9 C6H13 H Gal(″) H 8988 88 9 C8H17 H Gal(″) H 9089 89 9 C10H21 H Gal(″) H 7890 90 9 C12H25 H Gal(″) H 7991 91 9 (CH3)2CH H Gal(″) H 9092 92 9 4-甲基环己基 H Gal(″) H 8293 93 9 烯基 H Gal(″) H 81
表1(续)实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)94 94 9 3-己烯基 H Gal(″) H 7895 95 9 香叶基 H Gal(″) H 7696 96 9 苄基 H Gal(″) H 6997 97 13 乙酰基 H Glc(β-D式) 乙酰基 5898 98 13 乙酰基 CH3 Glc(″) 乙酰基 5699 99 13 丙酰基 C4H9 Glc(″) 乙酰基 48100 100 13 丙酰基 C10H21 Glc(″) 苄基 65101 101 13 丙酰基 C12H25 Glc(″) 苄基 71102 102 13 乙酰基 (CH3)2CH Glc(″) 苄基 72103 103 13 乙酰基 4-甲基环己基 Glc(″) 乙酰基 68104 104 13 乙酰基 乙烯基 Glc(″) 乙酰基 68105 105 13 乙酰基 3-己烯基 Glc(″) 乙酰基 69106 106 13 丁酰基 香叶基 Glc(″) 乙酰基 58107 107 13 丁酰基 苄基 Glc(″) 苄基 68108 108 19 H H Glc(β-D式) H 85109 109 19 H CH3 Glc(″) H 81110 110 19 H C4H9 Glc(″) H 78111 111 19 H C10H21 Glc(″) H 79112 112 19 H C12H25 Glc(″) H 81113 113 19 H (CH3)2CH Glc(″) H 89114 114 19 H 4-甲基环己基 Glc(″) H 78115 115 19 H 乙烯基 Glc(″) H 81116 116 19 H 3-己烯基 Glc(″) H 82117 117 19 H 香叶基 Glc(″) H 81
表1(续)实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)118 118 19 H 苄基 Glc(″) H 85119 119 14 乙酰基 H Man(α-D式) 乙酰基 62120 120 14 乙酰基 CH3 Man(″) 乙酰基 58121 121 14 丙酰基 C8H17 Man(″) 苄基 58122 122 14 丙酰基 C10H21 Man(″) 苄基 56123 123 14 丙酰基 C12H25 Man(″) 苄基 68124 124 14 乙酰基 (CH3)2CH Man(″) 苄基 61125 125 14 乙酰基 4-甲基环己基 Man(″) 乙酰基 69126 126 14 乙酰基 乙烯基 Man(″) 乙酰基 70127 127 14 乙酰基 3-己烯基 Man(″) 乙酰基 69128 128 14 丁酰基 香叶基 Man(″) 乙酰基 65129 129 14 丁酰基 苄基 Man(″) 苄基 68130 130 20 H H Man(α-D式) H 85131 131 20 H CH3 Man(″) H 81132 132 20 H C8H17 Man(″) H 78133 133 20 H C10H21 Man(″) H 76134 134 20 H C12H25 Man(″) H 79135 135 20 H (CH3)2CH Man(″) H 74136 136 20 H 4-甲基环己基 Man(″) H 68137 137 20 H 乙烯基 Man(″) H 79138 138 20 H 3-己烯基 Man(″) H 81139 139 20 H 香叶基 Man(″) H 71140 140 20 H 苄基 Man(″) H 83141 141 12 乙酰基 H Gal(β-D式) 乙酰基 82
表1(续)实施例 化合物 参考例 R1 R2 R3 R4 产率
(%)142 142 12 乙酰基 CH3 Gal(″) 乙酰基 62143 143 12 丙酰基 C10H21 Gal(″) 苄基 59144 144 12 丙酰基 C12H25 Gal(″) 苄基 68145 145 12 乙酰基 (CH3)2CH Gal(″) 苄基 71146 146 12 乙酰基 4-甲基环己基 Gal(″) 乙酰基 68147 147 12 乙酰基 乙烯基 Gal(″) 乙酰基 70148 148 12 乙酰基 3-己烯基 Gal(″) 乙酰基 69149 149 12 丁酰基 香叶基 Gal(″) 乙酰基 69150 150 12 丁酰基 苄基 Gal(″) 苄基 59151 151 21 H H Gal(β-D式) H 80152 152 21 H 苄基 Gal(″) H 76153 153 21 H CH3 Gal(″) H 82154 154 21 H C10H21 Gal(″) H 81155 155 21 H C12H25 Gal(″) H 68156 156 21 H (CH3)2CH Gal(″) H 72157 157 21 H 4-甲基环己基 Gal(″) H 78158 158 21 H 烯基 Gal(″) H 68159 159 21 H 3-己烯基 Gal(″) H 69160 160 21 H 香叶基 Gal(″) H 79化合物241H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.20(m,25H),6.88(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H),5.35~5.25(m,2H),5.20(m,8H),5.12(t,1H,J=8.0Hz),4.95(d,1H,J=8.0Hz),4.30~4.20(m,2H),3.85~3.81(m,1H),3.73(s,3H)IR(KBr,cm-1):1645,1600,1440,1380
元素分析,C51H48O10计算值(%):C 74.62;H 5.89;O 19.49测定值(%):C 74.53;H 5.88;O 19.59化合物251H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.15(m,25H),6.88(d,1H,J=8.8Hz),6.82(s,1H),5.42(s,2H),5.35~5.25(m,2H),5.22(m,8H),5.17(t,1H,J=8.0Hz),4.93(d,1H,J=8.0Hz),4.40(t,2H,J=6.8Hz),4.30~4.21(m,2H),3.85~3.81(m,1H),1.75~1.24(m,4H),0.93(t,3H,J=7.0Hz)IR(KBr,cm-1):1645,1610,1435,1380
元素分析,C54H54O10计算值(%):C 75.15;H 6.31;O 18.54测定值(%):C 75.23;H 6.28;O 18.49化合物261H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.60~7.20(m,5H)6.88(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H)5.35~5.25(m,2H),5.10(t,1H,J=8.0Hz),4.95(d,1H,J=8.0Hz),4.52(t,2H,J=6.5Hz),4.30~4.20(m,2H),3.85-3.80(m1H),2.20~2.00(m,12H),1.78~1.28(m,8H),0.89(t,3H J=7.0Hz)IR(KBr,cm-1):1765,1645,1610,1440,1380
元素分析,for C36H42O14计算值(%):C 61.89;H 6.06;O 32.05测定值(%):C 61.73;H 6.18;O 32.09化合物271H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.62~7.20(m,5H),6.90(d,1H,J=8.8Hz),6.80(s,1H),5.42(s,2H),5.35~5.25(m,2H),5.10(t,1H,J=8.0Hz),4.98(d,1H,J=8.0Hz),4.50(t,2H,J=6.5Hz),4.28~4.20(m,2H),3.843.80(m,1H),2.20~1.98(m,12H),1.80~1.25(m,12H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1765,1645,1600,1445,1380
元素分析,C38H46O14计算值(%):C 62.80;H 6.38;O 30.82测定值(%):FC 62.83;H 6.43;O 30.74化合物281H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.88(d,1H,J=8.8Hz),6.79(s,1H),5.42(s,2H),5.35~5.25(m,2H),5.08(t,1H,J=8.0Hz),4.97(d,1H,J=8.0Hz),4.52(t,2H,J=6.5Hz),4.30~4.18(m,2H),3.85~3.80(m,1H),2.22~2.00(m,12H),1.80~1.20(m,16H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1645 1610,1430,1380
元素分析,C40H50O14计算值(%):C 63.65;H 6.68;O 29.67测定值(%):C 63.53;H 6.78;O 29.69化合物291H-NMR(DMSO-d6,δ-TMS):7.73(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H),5.35~5.25(m,2H),5.12(t,1H,J=8.0Hz),4.95(d,1H,J=8.0Hz),4.52(t,2H,J=6.5Hz),4.27~4.18(m,2H),3.85~3.80(m,1H),2.20~2.00(m,12H),1.83~1.25(m,20H),0.90(t,3H,J=7.0Hz)IR(KBr,cm-1):1765,1640,1605,1440,1380
元素分析,C42H54O14计算值(%):C 64.44;H 6.95;O 28.61测定值(%):C 64.53;H 6.78;O 28.69化合物301H-NMR(DMSO-d6,δ-TMS):7.74(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.80(s,1H),5.42(s,2H),5.35~5.23(m,2H),5.12(t,1H,J=8.0Hz),4.97(d,1H,J=8.0Hz),4.51(m,1H),4.26~4.16(m,2H),3.83~3.78(m,1H),2.22~2.00(m,12H),1.03(d,6H,J=7.4Hz)IR(KBr,cm-1):1770,1650,1605,1435,1380
元素分析,C33H36O14计算值(%):C 60.36;H 5.53;O 34.11测定值(%):C 60.33;H 5.68;O 33.99化合物311H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.18(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),5.44(s,2H),5.32~5.24(m,2H),5.12(t,1H,J=8.0Hz),5.00(m,1.H),4.95(d,1H,J=8.0Hz),4.28~4.18(m,2H),3.84~3.80(m,1H),2.23~1.26(m,21H),0.96(d,3H,J=6.8Hz)IR(KBr,cm-1):1760,1640,1605,1445,1380
元素分析,C37H42O14计算值(%):C 62.53;H 5.96;O 31.51测定值(%):C 62.83;H 5.75;O 31.42化合物321H-NMR(DMSO-d6,δ-TMS):7.72(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.87(d,1H,J=8.8Hz),6.75(s,1H),6.44(dd,1H,J=17.5Hz,J=9.4Hz),5.42(s,2H),5.34~5.24(m,2H),5.12(t,1H,J=8.0Hz),4.95(d,1H,J=8.0Hz),4.28~4.16(m,2H),4.13(dd,1H,J=17.6Hz,J=2.0Hz),3.91(dd,1H,J=9.4Hz,J=1.9Hz),3.85~3.79(m,1H),2.19~2.00(m,12H)IR(KBr,cm-1):1765,1635,1600,1440,1375
元素分析,C32H32O14计算值(%):C 60.00;H 5.04;O 34.96测定值(%):C 59.93;H 5.08;O 34.99化合物331H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.58~7.20(m,5H),6.86(d,1H,J=8.8Hz),6.78(s,1H),5.42(s,2H),5.35~5.25(m,4H),5.10(t,1H,J=8.0Hz),4.97(d,1H,J=8.0Hz),4.28~4.22(m,4H),3.86~3.81(m,1H),2.30~1.94(m,16H),0.98(t,3H,J=7.2Hz)IR(KBr,cm-1):1765,1650,1610,1440,1370
元素分析,C36H40O14计算值(%):C 62.06;H 5.79;O 32.15测定值(%):C 62.13;H 5.78;O 32.09化合物341H-NMR(DMSO-d6,δ-TMS)7.74(d,1H,J=8.8Hz),7.62~7.22(m,5H),6.85(d,1H,J=8.8Hz),6.76(s,1H),5.42(s,2H),5.36~5.26(m,3H),5.10(m,2H),4.95(d,1H,J=8.0Hz),4.27~4.17(m,2H),4.12(d,2H,J=8.6Hz),3.86~3.80(m,1H),2.19~1.98(m,16H),1.68(s,6H),1.59(s,3H)IR(KBr,cm-1):1760,1645,1605,1440,1370
元素分析,C40H46O14计算值(%):C 63.99;H 6.18;O 29.83测定值(%):C 63.83;H 6.24;O 29.93化合物351H-NMR(DMSO-d6,δ-TMS):7.67(d,1H,J=8.8Hz),7.55~7.15(m,25H),6.73(d,1H,J=8.8Hz),6.80(s,1H),5.38(s,2H),5.37~5.24(m,2H),5.15(m,8H),5.10(t,1H,J=8.0Hz),4.96(d,1H,J=8.0Hz),4.51(t,2H,J=6.8Hz),4.24~4.19(m,2H),3.86~3.82(m,1H),1.77~1.20(m,12H),0.91(t,3H,J=7.0Hz)IR(KBr,cm-1):1645,1610,1440,1380
元素分析,C58H62O10计算值(%):C 75.79;H 6.80;O 17.41测定值(%):C 75.83;H 6.78;O 17.39化合物361H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.70~7.15(m,30H),6.90(d,1H,J=8.8Hz),6.79(s,1H),5.45(s,2H),5.35~5.25(m,2H),5.17(m,10H),5.08(t,1H,J=8.0Hz),4.90(d,1H,J=8.0Hz),4.29~4.21(m,2H),3.87~3.78(m 1H)IR(KBr,cm-1):1640,1605,1445,1370
元素分析,C57H52O10计算值(%):C 76.32;H 5.84 O 17.84测定值(%):C 76.53;H 5.78;O 17.69化合物371H-NMR(DMSO-d6,δ-TMS):10.32(bs,1H),7.59(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.39(bs,1H),5.11(bs,1H),5.06(bs,1H),4.96(d,1H,J=6.8Hz),4.60(bs,1H),4.25(t,2H,J=6.2Hz),3.76~3.10(m,6H),1.80~1.20(m,4H),0.88(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2960,2920,2840,1700,1645,1610,1260
元素分析,C19H24O10计算值(%):C 55.33;H 5.87;O 38.80测定值(%):C 55.29;H 5.89;O 38.82化合物381H-NMR(DMSO-d6,δ-TMS):10.45(bs,1H),7.61(d,1H,J=8.8Hz),7.11~7.02(m,2H),5.35(bs,1H),5.09(bs,1H),5.04(bs,1H),4.95(d,1H,J=7.2Hz),4.57(bs,1H),4.42(t,2H,J=6.4Hz),3.82~3.12(m,6H),1.80~1.20(m,8H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3345,2920,2850,1710,1635,1610,1250
元素分析,C21H28O10计算值(%):C 57.26;H 6.41;O 36.33测定值(%):C 57.20;H 6.35;O 36.45化合物391H-NMR(DMSO-d6,δ-TMS):10.40(bs,1H),7.60(d,1H,J=8.8Hz),7.12~7.02(m,2H),5.37(bs,1H),5.10(bs,1H),5.04(bs,1H),4.95(d,1H,J=7.2Hz),4.56(bs,1H),4.41(t,2H,J=6.4Hz),3.80~3.12(m,6H),1.82~1.13(m,12H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3350,2920,2845,1700,1635,1610,1250
元素分析,C23H32O10计算值(%):C 58.96;H 6.89;O 34.15测定值(%):C 59.06;H 6.77;O 34.17化合物401H-NMR(DMSO-d6,δ-TMS):10.20(bs,1H),7.62(d,1H,J=8.8Hz),7.12~7.02(m,2H),5.33(bs,1H),5.12(bs,1H),5.04(bs,1H),4.95(d,1H,J=7.2Hz),4.56(bs,1H),4.38(t,2H,J=6.4Hz),3.75~3.10(m,6H),1.85~1.15(m,16H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3340,2925,2845,1705,1650,1620,1250
元素分析,C23H32O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.45;H 7.35;O 32.20化合物411H-NMR(DMSO-d6,δ-TMS):10.45(bs,1H),7.60(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.39(bs,1H),5.13(bs,1H),5.05(bs,1H),4.95(d,1H,J=7.2Hz),4.57(bs,1H),4.25(t,2H,J=6.4Hz),3.80~3.18(m,6H),1.80~1.60(m,2H),1.52~1.12(m,18H),0.88(t,3H,J=6.8Hz)IR(KBr,cm-1):3350,2910,2850,1700,1650,1610,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.77;H 7.55;O 30.68化合物421H-NMR(DMSO-d6,δ-TMS):10.43(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.35(bs,1H),5.10(bs,1H),5.05(bs,1H),4.99(d,1H,J=6.8Hz),4.62(bs,1H),4.45(m,1H),3.75~3.10(m,6H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):3330,3300,2940,2850,1700,1600,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.28;H 5.69;O 40.03化合物431H-NMR(CDCl3,δ-TMS):10.38(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.01(m,2H),5.35(bs,1H),5.10(bs,1H),5.03(bs,1H),4.98(m,1H),4.93(d,1H,J=6.8Hz),4.53(bs,1H),3.80~3.09(m,6H),2.00~1.22(m,9H),0.95(d,3H,J=6.5Hz)IR(KBr,cm-1):3335,3300,2955,2850,1710,1620,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.35;H 6.29;O 35.36化合物441H-NMR(DMSO-d6,δ-TMS):10.48(bs,1H),7.65(d,1H,J=8.8Hz),7.13~7.03(m,2H),6.57(dd,1H,J=17.5Hz,J=9.5Hz),5.35(bs,1H),5.15(bs,1H),5.08(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.17(dd,1H,J=17.5Hz,J=2.0Hz),3.95(dd,1H,J=9.5Hz,J=2.0Hz),3.80~3.12(m,6H)IR(KBr,cm-1):3340,3310,2950,2845,1700,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.57;H 4.69;O 41.74化合物451H-NMR(DMSO-d6,δ-TMS):10.40(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.50(m,1H),5.34(m,2H),5.11(bs,1H),5.03(bs,1H),4.98(d,1H,J=6.8Hz),4.59(bs,1H),4.27(t,2H,J=6.2Hz),3.83~3.15(m,6H),2.25~1.96(m,4H),0.99(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2950,2920,1710,1640,1615,1260
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.65;H 5.89;O 36.46化合物461H-NMR(DMSO-d6,δ-TMS):10.35(bs,1H),7.61(d,1H,J=8.8Hz),7.12~7.00(m,2H),5.38(m,1H),5.34(bs,1H),5.10(m,2H),5.05(bs,1H),4.98(d,1H,J=6.8Hz),4.59(bs,1H),4.10(d,2H,J=8.5Hz),3.80~3.15(m,6H),2.05(m,4H),1.67(s,6H),1.60(s,3H)IR(KBr,cm-1):3345,2950,2920,1705,1640,1610,1260
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.85;H 6.70;O 32.45化合物471H-NMR(DMSO-d6,δ-TMS):10.50(bs,1H),7.61(d,1H,J=8.8Hz),7.30~7.15(m,5H),7.10~7.00(m,2H),5.35(bs,1H),5.25(s,2H),5.11(bs,1H),5.00(bs,1H4.93(d,1H,J=6.8Hz),4.55(bs,1H),3.80~3.10(m,6H)IR(KBr,cm-1):3340,3300,2955,2850,1710,1620,1260
元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.15;H 4.89;O 35.96化合物481H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.60~7.20(m,25H),6.88(d,1H,J=8.8Hz),6.75(s,1H),6.00(S,1H),5.54(m,2H),5.43(s,2H),5.39(m,1H),5.20(m,8H),4.24(m,2H),4.15(s,1H),3.73(s,3H)IR(KBr,cm-1):1645,1610,1440,1380
元素分析,C51H48O10计算值(%):C 74.62;H 5.89;O 19.49测定值(%):C 74.56;H 5.84;O 19.60化合物491H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.15(m,25H),6.88(d,1H,J=8.8Hz),6.75(s,1H),6.00(S,1H),5.55(s,2H),5.42(s,2H),5.40(m,1H),5.22(m,8H),4.42(t,2H,J=6.7Hz),4.25(m,2H),4.15(s,1H),1.75~1.24(m,4H),0.93(t,3H,J=7.0Hz)IR(KBr,cm-1):1645,1610,1435,1380
元素分析,C54H54O10计算值(%):C 75.15;H 6.31;O 18.54测定值(%):C 75.23;H 6.28;O 18.49化合物501H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.20(m,5H) 6.88(d,1H,J=8.8Hz),6.79(s,1H),6.02(s,1H),5.56(m,2H),5.42(s,2H),5.40(m,1H),4.50(t,2H,J=6.5Hz),4.24(m,2H),4.15(s,1H),2.18~1.98(m,12H),1.80~1.30(m,8H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1765,1645,1610,1435,1380
元素分析,C36H42O14计算值(%):C 61.89;H 6.06;O 32.05测定值(%):C 61.74;H 6.10;O 32.06化合物511H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.62~7.20(m,5H),6.90(d,1H,J=8.8Hz),6.80(s,1H),6.02(s,1H),5.56(m,2H),5.44(s,2H),5.41(m,1H),4.50(t,2H,J=6.5Hz),4.25(m,2H),4.13(s,1H),2.20~1.98(m,12H),1.80~1.25(m,12H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1640,1600,1445,1380
元素分析,C38H46O14计算值(%):C 62.80;H 6.38;O 30.82测定值(%):C 62.87;H 6.33;O 30.80化合物521H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.88(d,1H,J=8.8Hz),6.80(s,1H),6.03(s,1H),5.57(m,2H),5.42(s,2H),5.40(m,1H),4.52(t,2H,J=6.5Hz),4.25(m,2H),4.13(s,1H),2.23~2.00(m,12H),1.81~1.21(m,16H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1635,1600,1430,1380
元素分析,C40H50O14计算值(%):C 63.65;H 6.68 O 29.67测定值(%):C 63.63;H 6.85;O 29.52化合物531H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),6.02(s,1H),5.60(m,2H),5.43(s,2H),5.38(m,1H),4.51(t,2H,J=6.5Hz),4.23(m,2H),4.12(s,1H),2.20~2.02(m,12H),1.84~1.24(m,20H),0.90(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1640,1610,1440,1380
元素分析,C42H54O14计算值(%):C 64.44;H 6.95;O 28.61测定值(%):C 64.47;H 6.88;O 28.65化合物541H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.56~7.17(m,5H),6.85(d,1H,J=8.8Hz),6.80(s,1H),6.00(s,1H),5.59(m,2H),5.42(s,2H),5.39(m,1H),4.50(m,1H),4.23(m,2H),4.12(s,1H),2.22~2.00(m,12H),1.05(d,6H,J=7.4Hz)IR(KBr,cm-1):1770,1645,1605,1430,1380
元素分析,C33H36O14计算值(%):C 60.36;H 5.53;O 34.11测定值(%):C 60.39;H 5.64;O 33.97化合物551H-NMR(DMSO-d6,δ-TMS):7.72(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),6.02(s,1H),5.60(m,2H),5.44(s,2H),5.41(m,1H)5.00(m,1H),4.22(m,2H),4.13(s,1H),2.23~1.26(m,21H),0.96(d,3H,J=6.8Hz)IR(KBr,cm-1):1750,1640,1600,1445,1380
元素分析,C37H42O14计算值(%):C 62.53;H 5.96;O 31.51测定值(%):C 62.63;H 5.85;O 31.52化合物561H-NMR(DMSO-d6,δ-TMS):7.73(d,1H,J=8.8Hz),7.59~7.18(m,5H),6.87(d,1H,J=8.8Hz),6.74(s,1H),6.44(dd,1H,J=17.5Hz,J=9.4Hz),6.00(s,1H),5.50(m,2H),5.42(s,2H),5.40(m,1H),4.24(m,2H),4.15(s,1H),4.13(dd,1H,J=17.6Hz,J=2.0Hz),3.91(dd,1H,J=9.4Hz,J=1.9Hz),2.22~2.00(m,12H)IR(KBr,cm-1):1765,1640,1600,1435,1375
元素分析,C32H32O14计算值(%):C 60.00;H 5.04;O 34.96测定值(%):C 59.97;H 5.10;O 34.93化合物571H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.58~7.20(m,5H),6.86(d,1H,J=8.8Hz),6.78(s,1H),6.00(s,1H),5.50(m,2H),5.43(s,2H),5.41(m,1H),5.34(m,2H),4.26(t,2H,J=6.2Hz),4.23(m,2H),4.14(s,1H),2.30~1.96(m,16H),0.98(t,3H,J=7.2Hz)IR(KBr,cm-1):1760,1650,1610,1440,1370
元素分析,C36H40O14计算值(%):C 62.06;H 5.79;O 32.15测定值(%):C 62.03;H 5.88;O 32.09化合物581H-NMR(DMSO-d6,δ-TMS):7.72(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.76(s,1H),6.02(s,1H),5.50(m,2H),5.44(s,2H),5.41(m,1H),5.35(m,1H),5.13(m,1H),4.23(m,2H),4.14(s,1H),4.12(d,2H,J=8.6Hz),2.20~1.98(m,16H),1.68(s,6H),1.58(s,3H)IR(KBr,cm-1):1765,1645,1600,1440,1370
元素分析,C40H46O14计算值(%):C 63.99;H 6.18;O 29.83测定值(%):C 63.88;H 6.23;O 29.89化合物591H-NMR(DMSO-d6,δ-TMS):7.69(d,1H,J=8.8Hz),7.55~7.15(m,25H),6.73(d,1H,J=8.8Hz),6.81(s,1H),6.01(s,1H),5.49(m,2H),5.40(m,1H),5.36(s,2H),5.15(m,8H),4.49(t,2H,J=6.8Hz),4.23(m,2H),4.14(s,1H),1.80~1.20(m,12H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1650,1610,1435,1380
元素分析,C58H62O10计算值(%):C 75.79;H 6.80;O 17.41测定值(%):C 75.87;H 6.74;O 17.39化合物601H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.15(m,30H),6.90(d,1H,J=8.8Hz),6.80(s,1H),6.01(s,1H),5.49(m,2H),5.46(s,2H),5.41(m,1H),5.17(m,10H),4.22(m,2H),4.15(s,1H)IR(KBr,cm-1):1640,1600,1445,1370
元素分析,C57H52O10计算值(%):C 76.32;H 5.84;O 17.84测定值(%):C 76.56;H 5.79;O 17.65化合物611H-NMR(DMSO-d6,δ-TMS):10.13(s,1H),9.20(bs,1H),7.61(d,1H,J=8.8Hz),7.15(d,1H,J=2.4Hz),7.10(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.09(bs,1H),4.85(bs,1H),4.80(bs,1H),3.85(s,1H),3.75~3.25(m,6H)IR(KBr,cm-1):3340,2950,2910,2850,1690,1620,1610,1250
元素分析,C15H16O10计算值(%):C 50.56;H 4.53;O 44.91测定值(%):C 50.42;H 4.58;O 45.00化合物621H-NMR(DMSO-d6,δ-TMS):10.35(bs,1H),7.57(d,1H,J=8.8Hz),7.14(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.08(bs,1H),4.90(bs,1H),4.77(bs,1H),4.45(t,2H,J=6.4Hz),3.87(s,1H),3.78~3.20(m,6H),1.75~1.20(m,4H),0.86(t,3H,J=7.2Hz)IR(KBr,cm-1):3345,2950,2900,2850,1690,1635,1600,1250
元素分析,C19H24O10计算值(%):C 55.33;H 5.87;O 38.80测定值(%):C 55.35;H 5.90;O 38.75化合物631H-NMR(DMSO-d6,δ-TMS):10.15(bs,1H),7.56(d,1H,J=8.8Hz),7.12(d,1HJ=2.4Hz),7.09(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),6.05(bs,1H),4.90(bs,1H),4.77(bs,1H),4.45(t,2H,J=6.4Hz),3.86(s,1H),3.75~3.20(m,6H),1.70~1.30(m,8H),0.90(t,3H,J=7.2Hz)IR(KBr,cm-1):3355,2950,2900,2850,1670,1630,1610,1250
元素分析,C21H28O10计算值(%):C 57.26;H 6.41;O 36.33测定值(%):C 57.35;H 6.35;O 36.30化合物641H-NMR(DMSO-d6,δ-TMS):10.25(bs,1H),7.58(d,1H,J=8.8Hz),7.14(d,1H,J=2.4Hz),7.09(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.08(bs,1H),4.89(bs,1H),4.77(bs,1H),4.45(t,2H,J=6.4Hz),3.87(s,1H),3.76~3.23(m,6H),1.80~1.30(m,12H),0.87(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2910,2850,1680,1635,1610,1250
元素分析,C23H32O10计算值(%):C 58.96;H 6.89;O 34.15测定值(%):C 58.85;H 6.85;O 34.30化合物651H-NMR(DMSO-d6,δ-TMS):10.05(bs,1H),7.61(d,1H,J=8.8Hz),7.15(d,1H,J=2.4Hz),7.09(dd,1H,J=2.2Hz,J=9.0Hz),5.45(s,1H),5.09(bs,1H),4.85(bs,1H),4.74(bs,1H),4.42(t,2H,J=6.4Hz),3.85(s,1H),3.80~3.25(m,6H),1.75~1.20(m,16H),0.88(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2940,2920,2850,1680,1630,1610,1245
元素分析,C25H36O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.45;H 7.40;O 32.15化合物661H-NMR(DMSO-d6,δ-TMS):9.85(bs,1H),7.60(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.08(bs,1H),4.90(bs,1H),4.80(bs,1H),4.42(t,2H,J=6.4Hz),3.88(s,1H),3.70~3.15(m,6H),1.95~1.20(m,20H),0.85(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2915,2850,1685,1630,1600,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.75;H 7.55;O 30.70化合物671H-NMR(DMSO-d6,δ-TMS):9.98(bs,1H),7.63(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.08(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.87(bs,1H),4.76(bs,1H),4.43(m,1H),3.88(s,1H),3.78~3.12(m,6H),1.07(d,6H,J=7.5Hz)IR(KBr,cm-1):3330,2950,2910,2845,1690,1630,1615,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.18;H 5.65;O 40.17化合物681H-NMR(CDCl3,δ-TMS):10.00(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.89(bs,1H),4.76(bs,1H),3.75~3.25(m,6H),2.25~1.20(m,9H),0.97(d,3H,J=6.7Hz)IR(KBr,cm-1):3335,2940,2920,2855,1690,1625,1610,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.33;H 6.34;O 35.33化合物691H-NMR(DMSO-d6,δ-TMS):10.10(bs,1H),7.60(d,1H,J=8.8Hz),7.13(d,1H,J=2.4Hz),7.08(dd,1H,J=2.2Hz,J=9.0Hz),6.45(dd,1H,J=17.5Hz,J=9.5Hz),5.50(s,1H),5.10(bs,1H),4.87(bs,1H),4.77(bs,1H),4.13(dd,1H,J=17.5Hz,J=2.0Hz),3.95(dd,1H,J=9.5Hz,J=2.0Hz),3.87(s,1H),3.76~3.21(m,6H)IR(KBr,cm-1):3335,2950,2920,2840,1695,1630,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.43;H 4.80;O 41.77化合物701H-NMR(DMSO-d6,δ-TMS):9.78(bs,1H),7.58(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.54(m,1H),5.35(m,2H),5.08(bs,1H),4.85(bs,1H),4.78(bs,1H),4.27(t,2H,J=6.2Hz),3.88(s,1H),3.70~3.25(m,6H),2.25~1.90(m,4H),0.99(t,3H,J=7.0Hz)IR(KBr,cm-1):3340,2950,2910,2850,1685,1630,1615,1250
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.60;H 5.83;O 36.57化合物711H-NMR(DMSO-d6,δ-TMS):9.95(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.41(m,1H),5.16(m,1H),5.09(bs,1H),4.87(bs,1H),4.77(bs,1H),4.10(d,2H,J=8.5Hz),3.85(s,1H),3.75~3.25(m,6H),2.00(m,4H),1.64(s,6H),1.58(s,3H)IR(KBr,cm-1):3335,2950,2920,2845,1690,1620,1600,1250
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.89;H 6.60;O 32.51化合物721H-NMR(DMSO-d6,δ-TMS):10.30(bs,1H),7.60(d,1H,J=8.8Hz),7.38(m,5H),7.15(d,1H,J=2.4Hz),7.09(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.25(s,2H),5.07(bs,1H),4.90(bs,1H),4.79(bs,1H),3.85(s,1H),3.76~3.20(m,6H)IR(KBr,cm-1):3335,2960,2930,2850,1680,1630,1610,1250
元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.25;H 4.89;O 35.86化合物731H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.60~7.20(m,25H),6.88(d,1H,J=8.8Hz),6.75(s,1H),6.00(S,1H),5.54(m,2H),5.43(s,2H),5.39(s,1H),5.25~5.15(m,9H),4.20~4.11(m,2H),3.73(s,3H)IR(KBr,cm-1):1645,1610,1440,1380
元素分析,C51H48O10计算值(%):C 74.62;H 5.89;O 19.49测定值(%):C 74.56;H 5.84;O 19.60化合物741H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.15(m,25H),6.88(d,1H,J=8.8Hz),6.75(s,1H),6.00(S,1H),5.55(s,2H),5.42(s,2H),5.40(s,1H),5.26~5.16(m,9H),4.42(t,2H,J=67Hz),4.22~4.09(m,2H),1.75~1.24(m,4H),0.93(t,3H,J=7.0Hz)IR(KBr,cm-1):1645,1610,1435,1380
元素分析,C54H54O10计算值(%):C 75.15;H 6.31;O 18.54测定值(%):C 75.23;H 6.28;O 18.49Compund 751H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.88(d,1H,J=8.8Hz),6.79(s,1H),6.02(s,1H),5.56(m,2H),5.42(s,2H),5.40(s,1H),5.24~5.16(m,1H),4.50(t,2H,J=6.5Hz),4.20~4.08(m,2H),2.18~1.98(m,12H),1.80~1.30(m,8H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1765,1645,1610,1435,1380
元素分析,C36H42O14计算值(%):C 61.89;H 6.06;O 32.05测定值(%):C 61.74;H 6.10;O 32.06化合物761H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.62~7.20 (m,5H),6.90(d,1H,J=8.8Hz),6.80(s,1H),6.02(s,1H),5.56(m,2H),5.44(s,2H),5.41(s,1H)5.22~5.14(m,1H),4.50(t,2H,J=6.5Hz),4.20~4.10(m,2H),2.20~1.98(m,12H,1.80~1.25(m,12H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1640,1600,1445,1380
元素分析,C38H46O14计算值(%):C 62.80;H 6.38;O 30.82测定值(%):C 62.87;H 6.33;O 30.80化合物771H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.88(d,1H,J=8.8Hz),6.80(s,1H),6.03(s,1H),5.57(m,2H),5.42(s,2H),5.40(s,1H),5.23~5.15(m,1H),4.52(t,2H,J=6.5Hz),4.21~4.08(m,2H),2.23~2.00(m,12H),1.81~1.21(m,16H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1635,1600,1430,1380
元素分析,C40H50O14计算值(%):C 63.65;H 6.68;O 29.67测定值(%):C 63.63;H 6.85;O 29.52化合物781H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),6.02(s,1H),5.60(m,2H),5.43(s,2H),5.38(s,1H),5.22~5.13(m,1H),4.51(t,2H,J=6.5Hz),4.20~4.09(m,2H),2.20~2.02(m,12H),1.84~1.24(m,20H),0.90(t,3H,J=7.0Hz)IR(KBr,cm-1):1760,1640,1610,1440,1380
元素分析,C42H54O14计算值(%):C 64.44;H 6.95;O 28.61测定值(%):C 64.47;H 6.88;O 28.65化合物791H-NMR(DMSO-d6,δ-TMS):7.71(d,1H,J=8.8Hz),7.56~7.17(m,5H),6.85(d,1H,J=8.8Hz),6.80(s,1H),6.00(s,1H),5.59(m,2H),5.42(s,2H),5.39(s,1H),5.24~5.16(m,1H),4.50(m,1H),4.19~4.08(m,2H),2.22~2.00(m,12H),1.05(d,6H,J=7.4Hz)IR(KBr,cm-1):1770,1645,1605,1430,1380
元素分析,C33H36O14计算值(%):C 60.36;H 5.53;O 34.11测定值(%):C 60.39;H 5.64;O 33.97化合物801H-NMR(DMSO-d6,δ-TMS):7.72(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.78(s,1H),6.02(s,1H),5.60(m,2H),5.44(s,2H),5.41(s,1H),5.23~5.14(m,1H),5.00(m,1H),4.21~4.09(m,2H),2.23~1.26(m,21H),0.96(d,3H,J=6.8Hz)IR(KBr,cm-1):1750,1640,1600,1445,1380
元素分析,C37H42O14计算值(%):C 62.53;H 5.96;O 31.51测定值(%):C 62.63;H 5.85;O 31.52化合物811H-NMR(DMSO-d6,δ-TMS):7.73(d,1H,J=8.8Hz),7.59~7.18(m,5H),6.87(d,1H,J=8.8Hz),6.74(s,1H),6.44(dd,1H,J=17.5Hz,J=9.4Hz),6.00(s,1H),5.50(m,2H),5.42(s,2H),5.40(s,1H),5.23~5.15(m,1H),4.20~4.10(m,2H),4.13(dd,1H,J=17.6Hz,J=2.0Hz),3.91(dd,1H,J=9.4Hz,J=1.9Hz),2.22~2.00(m,12H)IR(KBr,cm-1):1765,1640,1600,1435,1375
元素分析,C32H32O14计算值(%):C 60.00;H 5.04;O 34.96测定值(%):C 59.97;H 5.10;O 34.93化合物821H-NMR(DMSO-d6,δ-TMS):7.70(d,1H,J=8.8Hz),7.58~7.20(m,5H),6.86(d,1H,J=8.8Hz),6.78(s,1H),6.00(s,1H),5.50(m,2H),5.43(s,2H),5.41(s,1H),5.34(m,2H),5.21~5.13(m,1H),4.26(t,2H,J=6.2Hz),4.20~4.12(m,2H),2.30~1.96(m,16H),0.98(t,3H,J=7.2Hz)IR(KBr,cm-1):1760,1650,1610,1440,1370
元素分析,C36H40O14计算值(%):C 62.06;H 5.79;O 32.15测定值(%):C 62.03;H 5.88;O 32.09化合物831H-NMR(DMSO-d6,δ-TMS):7.72(d,1H,J=8.8Hz),7.60~7.20(m,5H),6.85(d,1H,J=8.8Hz),6.76(s,1H),6.02(s,1H),5.50(m,2H),5.44(s,2H),5.41(s,1H),5.34(m,1H),5.20~5.13(m,2H),4.19~4.11(m,2H),4.12(d,2H,J=8.6Hz),2.20~1.98(m,16H),1.68(s,6H),1.58(s,3H)IR(KBr,cm-1):1765,1645,1600,1440,1370
元素分析,C40H46O14计算值(%):C 63.99;H 6.18;O 29.83测定值(%):C 63.88;H 6.23;O 29.89化合物841H-NMR(DMSO-d6,δ-TMS):7.69(d,1H,J=8.8Hz),7.55~7.15(m,25H),6.73(d,1H,J=8.8Hz),6.81(s,1H),6.01(s,1H),5.49(m,2H),5.40(s,1H),5.36(s,2H),5.22~5.14(m,9H),4.49(t,2H,J=6.8Hz),4.18~4.10(m,2H),1.80~1.20(m,12H),0.89(t,3H,J=7.0Hz)IR(KBr,cm-1):1650,1610,1435,1380
元素分析,C58H62O10计算值(%):C 75.79;H 6.80;O 17.41测定值(%):C 75.87;H 6.74;O 17.39化合物851H-NMR(DMSO-d6,δ-TMS):7.68(d,1H,J=8.8Hz),7.60~7.15(m,30H),6.90(d,1H,J=8.8Hz),6.80(s,1H),6.01(s,1H),5.49(m,2H),5.46(s,2H),5.41(s,1H),5.22~5.15(m,11H),4.18~4.09(m,2H)IR(KBr,cm-1):1640,1600,1445,1370
元素分析,C57H52O10计算值(%):C 76.32;H 5.84;O 17.84测定值(%):C 76.56;H 5.79;O 17.65化合物861H-NMR(DMSO-d6,δ-TMS):10.25(bs,1H),7.60(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.22(bs,1H),4.96(d,1H,J=7.6Hz),4.90(bs,1H),4.68(bs,1H),4.55(bs,1H),4.50(t,2H,J=6.6Hz),3.64~3.24(m,6H),1.75~1.20(m,4H),0.88(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2940,2900,2840,1670,1635,1610,1250
元素分析,C19H24O10计算值(%):C 55.33;H 5.87;O 38.80测定值(%):C 55.30;H 5.93;O 38.77化合物871H-NMR(DMSO-d6,δ-TMS):10.35(bs,1H),7.61(d,1H,J=9.6Hz),7.08~6.98(m,2H),5.20(bs,1H),4.97(d,1H,J=7.6Hz),4.90(bs,1H),4.68(bs,1H),4.54(bs,1H),4.49(t,2H,J=6.6Hz),3.65~3.24(m,6H),1.81~1.20(m,8H),0.90(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2960,2900,2840,1675,1630,1610,1250
元素分析,C21H28O10计算值(%):C 57.26;H 6.41;O 36.33测定值(%):C 57.40;H 6.40;O 36.20化合物881H-NMR(DMSO-d6,δ-TMS):10.10(bs,1H),7.62(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.20(bs,1H),4.98(d,1H,J=7.6Hz),4.90(bs,1H),4.65(bs,1H),4.52(bs,1H),4.52(t,2H,J=6.6Hz),3.64~3.24(m,6H),1.80~1.15(m,12H),0.89(t,3H,J=7.2Hz)IR(KBr,cm-1):3450,2940,2910,2850,1675,1630,1610,1250
元素分析,C23H32O10计算值(%):C 58.96;H 6.89;O 34.15测定值(%):C 58.90;H 6.93;O 34.17化合物891H-NMR(DMSO-d6,δ-TMS):10.15(bs,1H),7.60(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.20(bs,1H),4.95(d,1H,J=7.6Hz),4.90(bs,1H),4.68(bs,1H),4.52(bs,1H),4.49(t,2H,J=6.6Hz),3.64~3.24(m,6H),1.81~1.20(m,16H),0.92(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2940,2900,2850,1670,1630,1610,1250
元素分析,C25H36O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.40;H 7.40;O 32.20化合物901H-NMR(DMSO-d6,δ-TMS):10.20(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.01(m,2H),5.24(bs,1H),4.91(d,1H,J=7.6Hz),4.88(bs,1H),4.65(bs,1H),4.50(bs,1H),4.49(t,2H,J=6.6Hz),3.65~3.25 (m,6H),1.79~1.20(m,20H),0.88(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2945,2920,2850,1675,1630,1600,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.75;H 7.50;O 30.75化合物911H-NMR(DMSO-d6,δ-TMS):10.30(bs,1H),7.59(d,1H,J=9.6Hz),7.12~7.02(m,2H),5.20(bs,1H),4.93(d,1H,J=7.6Hz),4.85(bs,1H),4.67(bs,1H),4.49(m,2H),3.65~3.25(m,6H),1.04(d,6H,J=7.5Hz)IR(KBr,cm-1):3400,2960,2930,2850,1690,1635,1610,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.17;H 5.57;O 40.26化合物921H-NMR(CDCl3,δ-TMS):10.40(bs,1H),7.60(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.20(bs,1H),5.03(m,1H),4.90(d,1H,J=7.6Hz),4.88(bs,1H),1.66(bs,1H),4.55(bs,1H),3.63~3.23(m,6H),2.19~1.13(m,9H),0.95(d,3H,J=6.8Hz)IR(KBr,cm-1):3340,2970,2920,2850,1680,1635,1610,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.35;H 6.30;O 35.35化合物931H-NMR(DMSO-d6,δ-TMS):9.85(bs,1H),7.59(d,1H,J=9.6Hz),7.09~6.99(m,2H),6.45(dd,1H,J=17.5Hz,J=9.5Hz),5.20(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.68(bs,1H),4.52(bs,1H),4.15(dd,1H,J=17.5Hz,J=2.0Hz),3.93(dd,1H,J=9.5Hz,J=2.0Hz),3.64~3.24(m,6H),IR(KBr,cm-1):3360,2950,2900,2850,1670,1630,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.51;H 4.78;O 41.71化合物941H-NMR(DMSO-d6,δ-TMS):9.73(bs,1H),7.61(d,1H,J=9.6Hz),7.11~7.01(m,2H),5.50(m,1H),5.35(m,1H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.91(bs,1H),4.67(bs,1H),4.50(bs,1H),4.27(t,2H,J=6.2Hz),3.65~3.25(m,6H),2.33~1.97(m,4H),0.99(t,3H,J=7.0Hz)IR(KBr,cm-1):3340,2950,2920,1710,1630,1605,1260
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.67;H 5.95;O 36.38化合物951H-NMR(DMSO-d6,δ-TMS):10.29(bs,1H),7.61(d,1H,J=9.6Hz),7.09~7.00(m,2H),5.40(m,1H),5.21(bs,1H),5.11(m,1H),4.94(d,1H,J=7.6Hz),4.86(bs,1H),4.67(bs,1H),4.52(bs,1H),4.15(d,2H,J=8.5Hz),3.66~3.26(m,6H),2.01(m,4H),1.67(s,6H),1.64(s,3H)IR(KBr,cm-1):3350,2950,2915,1700,1660,1605,1260
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.93;H 6.62;O 32.45化合物961H-NMR(DMSO-d6,δ-TMS):10.13(bs,1H),7.60(d,1H,J=9.6Hz),7.34(m,5H),7.10~7.05(m,2H),5.28(s,2H),5.19(bs,1H),4.92(d,1H,J=7.6Hz),4.90(bs,1H),4.67(bs,1H),4.52(bs,1H),3.65~3.24(m,6H)IR(KBr,cm-1):3330,3300,2930,2840,1700,1620,1260
元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.28;H 4.85;O 35.87化合物971H-NMR(DMSO-d6,δ-TMS):9.55(s,1H),7.77(d,1H,J=8.8Hz),7.12(d,1HJ=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1HJ=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m3H),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):3320,2950,1750,1620,1370,1240
元素分析,C25H26O15计算值(%):C 53.00;H 4.59;O 42.41测定值(%):C 52.95;H 4.55;O 42.50化合物981H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,3H),4.15(s,3H),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C26H28O15计算值(%):C 53.79;H 4.83;O 41.38测定值(%):C 53.85;H 4.79;O 41.36化合物991H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.46(t,2H,J=6.0Hz),4.40~4.10(m,3H),2.25(q,2H,J=7.2Hz),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),1.80~1.70(m,2H),1.55~1.40(m,2H),1.05(t,3H,J=7.2Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,2920,2850,1730,1640,1610,1260
元素分析,C30H36O15计算值(%):C 56.60;H 5.66;O 37.74测定值(%):C 56.55;H 5.79;O 37.66化合物1001H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.35~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.30~5.18(m,8H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.46(t,2H,J=6.0Hz),4.40~4.10(m,3H),2.25(q,2H,J=7.2Hz),1.95~1.40(m,16H),1.07(t,3H,J=7.2Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1725,1640,1610,1250
元素分析,C56H64O11计算值(%):C 73.68;H 7.02;O 19.30测定值(%):C 73.65;H 7.05;O 19.30化合物1011H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.40~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.30~5.18(m,8H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.46(t,2H,J=6.0Hz),4.40~4.10(m,3H),2.05~1.40(m,20H),1.05(t,3H,J=7.4Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1700,1640,1610,1250
元素分析,C58H68O11计算值(%):C 74.04;H 7.23;O 18.73测定值(%):C 74.08;H 7.35;O 18.57化合物1021H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.40~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.30~5.18(m,8H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,4H),2.25(s,3H),1.05(d,J=75Hz,6H)IR(KBr,cm-1):2950,2850,1735,1610,1250
元素分析,C48H48O11计算值(%):C 72.00;H 6.00;O 22.00测定值(%):C 71.95;H 5.96;O 22.09化合物1031H-NMR(CDCl3,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.99(m,1H),4.40~4.10(m,3H),2.34(s,3H),2.20~1.25(m,9H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),0.98(d,3H,J=6.4Hz)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C32H38O15计算值(%):C 58.00,H 5.74;O 36.26测定值(%):C 57.95;H 5.79;O 36.26化合物1041H-NMR(DMSO-d6,δ-TMS):77.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),6.45(dd,1H,J=17Hz,J=9.5Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,4H),3.95(dd,1H,J=9.5Hz),J=2.0Hz),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):2950,2850,1725,1605,1250
元素分析,C27H28O15计算值(%):C 54.73;H 4.73;O 40.54测定值(%):C 54.85;H 4.69;O 40.46化合物1051H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.34(m,2H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,5H),2.34(s,3H),2.30~1.95(m,4H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):2950,2850,1720,1610,1250
元素分析,C31H36O15计算值(%):C 57.41;H 5.56;O 37.03测定值(%):C 57.45;H 5.59;O 36.96化合物1061H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.11(m,2H),5.04(t,1H,J=9.8Hz),4.40~4.22(m,3H),4.10(d,2H,J=8.5Hz),2.30(m,4H),2.05(m,2H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s3H),1.85(m,2H),1.67(s,6H),1.60(s,3H),1.55(m,2H),1.05(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,2850,1735,1620,1260
元素分析,C37H46O15计算值(%):C 60.82;H 6.30;O 32.88测定值(%):C 60.85;H 6.35;O 32.80化合物1071H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.35~7.15(m,25H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.20~5.35(m,10H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.15(m,3H),2.30(t,2H,J=6.8Hz),1.55(m,2H),1.05(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,2850,1705,1620,1260
元素分析,C54H52O11计算值(%):C 73.97;H 5.94;O 20.09测定值(%):C 73.95;H 5.96;O 20.09化合物1081H-NMR(DMSO-d6,δ-TMS):10.45(s,1H,9.19(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),3.75~3.10(m,6H)IR(KBr,cm-1):3330,3300,2950,2850,1700,1600,1260
元素分析,C15H16O10计算值(%):C 50.56;H 4.53;O 44.91测定值(%):C 50.55;H 4.49;O 44.96化合物1091H-NMR(DMSO-d6,δ-TMS):9.25(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.35(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.23(s,3H),3.75~3.10(m,6H)IR(KBr,cm-1):3330,3300,2950,2850,1700,1610,1250
元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.85;H 4.79;O 43.36化合物1101H-NMR(DMSO-d6,δ-TMS):9.19(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.25(t,2H,J=6.2Hz),3.75~3.10(m,6H),1.80~1.20(m,4H),0.85(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2950,2920,2850,1700,1640,1610,1260
元素分析,C19H24O10计算值(%):C 55.33;H 5.87;O 38.80测定值(%):C 55.25;H 5.89;O 38.86化合物1111H-NMR(DMSO-d6,δ-TMS):9.10(bs,1H),7.60(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.95(d,1H,J=7.2Hz),4.59(bs,1H),4.40(t,2H,J=6.4Hz),3.75~3.10(m,6H),1.80~1.60(m,2H),1.52~1.15(m,14H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3350,2920,2850,1700,1640,1610,1250
元素分析,C25H36O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.35;H 7.45;O 32.20化合物1121H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.60(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.37(bs,1H),5.11(bs,1H),5.05(bs,1H),4.95(d,1H,J=7.2Hz),4.59(bs,1H),4.25(t,2H,J=6.4Hz),3.75~3.10(m,6H),1.80~1.60(m,2H),1.52~1.12(m,18H),0.85(t,3H,J=6.8Hz)IR(KBr,cm-1):3350,2920,2850,1700,1640,1610,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.75;H 7.45;O 30.80化合物1131H-NMR(DMSO-d6,δ-TMS):9.25(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.35(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.45(m,1H),3.75~3.10(m,6H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):3330,3300,2950,2850,1700,1610,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.18;H 5.69;O 40.13化合物1141H-NMR(CDCl3,δ-TMS):9.25(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.35(bs,1H),5.11(bs,1H),5.05(bs,1H),5.00(m,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),3.75~3.10(m,6H),2.02~1.20(m,9H),0.98(d,3H,J=6.5Hz)IR(KBr,cm-1):3330,3300,2950,2850,1700,1610,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.45;H 6.29;O 35.26化合物1151H-NMR(DMSO-d6,δ-TMS):9.25(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),6.55(dd,1H,J=17.5Hz,J=9.5Hz),5.35(bs,1H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.16(dd,1H,J=17.5Hz,J=2.0Hz),3.95(dd,1H,J=9.5Hz,J=2.0Hz),3.75~3.10(m,6H)IR(KBr,cm-1):3330,3300,2950,2850,1700,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.55;H 4.79;O 41.66化合物1161H-NMR(DMSO-d6,δ-TMS):9.19(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.55(m,1H),5.34(m,2H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.27(t,2H,J=6.2Hz),3.75~3.10(m,6H),2.30~1.95(m,4H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2950,2920,1700,1640,1605,1260
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.75;H 5.79;O 36.46化合物1171H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.61(d,1H,J=8.8Hz),7.10~7.00(m,2H),5.40(m,1H),5.37(bs,1H),5.11(m,2H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),4.12(d,2H,J=8.5Hz),3.75~3.10(m,6H),2.05(m,4H),1.67(s,6H),1.60(s,3H)IR(KBr,cm-1):3350,2950,2920,1700,1640,1605,1260
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.85;H 6.75;O 32.40化合物1181H-NMR(DMSO-d6,δ-TMS):9.19(bs,1H),7.61(d,1H,J=8.8Hz),7.35~7.20(m,5H),7.10~7.00(m,2H),5.37(bs,1H),5.25(s,2H),5.11(bs,1H),5.05(bs,1H),4.96(d,1H,J=6.8Hz),4.59(bs,1H),3.75~3.10(m,6H)IR(KBr,cm-1):3330,3300,2950,2850,1700,1620,1260Eleme元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.25;H 4.79;O 35.96化合物1191H-NMR(DMSO-d6,δ-TMS):9.55(s,1H),7.77(d,1H,J=8.8Hz),7.30~7.15(m,2H),5.94(s,1H),5.45~5.35(m,2H),5.13(t,1H,J=10.0Hz),4.20~3.90(m,3H),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):3320,2950,1750,1620,1370,1240
元素分析,C25H26O15计算值(%):C 53.00;H 4.59;O 42.41测定值(%):C 52.95;H 4.55;O 42.50化合物1201H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.30~7.15(m,2H),5.94(s,1H),5.45~5.35(m,2H),5.13(t,1H,J=10Hz),4.20~3.90(m,3H),4.15(s,3H),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C26H28O15计算值(%):C 53.79;H 4.83;O 41.38测定值(%):C 53.85;H 4.79;O 41.36化合物1211H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.30~7.15(m,22H),5.94(s,1H),5.45~5.35(m,2H),5.25(m,8H),5.13(t,1H,J=10.0Hz),4.20~3.90(m,3H),4.46(t,2H,J=6.0Hz),2.25(q,2H,J=7.2Hz),1.80~1.40(m,12H),1.05(t,3H,J=7.2Hz),0.95(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,2920,2850,1730,1640,1610,1260
元素分析,C54H60O11计算值(%):C 73.30;H 6.78;O 19.92测定值(%):C 73.35;H 6.80;O 19.85化合物1221H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.35~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.94(s,1H),5.45~5.35(m,2H),5.30~5.18(m,8H),5.13(t,1H,J=10.0Hz),4.20~3.90(m,3H),4.46(t,2H,J=6.0Hz),2.23(q,2H,J=7.0Hz),1.95~1.40(m,16H),1.07(t,3H,J=7.0Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1725 1640,1610,1250
元素分析,C56H64O11计算值(%):C 73.68;H 7.02;O 19.30测定值(%):C 73.65;H 7.05;O 19.30化合物1231H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.40~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.30~5.18(m,8H)5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.46(t,2H,J=6.0Hz),4.40~4.10(m,3H),2.34(s,3H),2.26(q,2H,J=7.0Hz),2.05~1.40(m,20H),1.05(t,3H,J=7.0Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1700,1640,1610,1250
元素分析,C58H68O11计算值(%):C 74.04;H 7.23;O 18.73测定值(%):C 74.08;H 7.35;O 18.57化合物1241H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.40~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.18~5.30(m,8H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,4H),2.25(s,3H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):2950,2850,1735,1610,1250
元素分析,C48H48O11计算值(%):C 72.00;H 6.00;O 22.00测定值(%):C 71.95;H 5.96;O 22.09化合物1251H-NMR(CDCl3,δ-TMS):7.77(d,1H,J=8.8Hz),7.30~7.15(m,2H),5.94(s,1H),5.45~5.35(m,2H),5.13(t,1H,J=10.0Hz),5.05(m,1H)4.20(3.90(m,3H,2.3)(s,3H),2.20~1.25(m,9H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),0.95(d,3H,J=6.6Hz)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C32H38O15计算值(%):C 58.00;H 5.74;O 36.26测定值(%):C 58.04;H 5.79;O 36.17化合物1261H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.30~7.15(m,2H),5.94(s,1H),6.45(dd,1H,J=17.5Hz,J=9.5Hz),5.45~5.35(m,2H),5.13(t,1H,J=10.0Hz),4.20~3.90(m,5H),2.34(s,3H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C27H28O15计算值(%):C 54.73;H 4.73;O 40.54测定值(%):C 54.75;H 4.79;O 40.46化合物1271H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz)5.34(m,2H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,5H),2.34(s,3H),2.30~1.95(m,4H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):2950,2850,1735,1610,1250
元素分析,C31H36O15计算值(%):C 57.41;H 5.56;O 37.03测定值(%):C 57.45;H 5.59;O 36.96化合物1281H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.11(m,2H),5.04(t,1H,J=9.8Hz),4.40~4.22(m,3H),4.12(d,2H,J=8.5Hz),2.30(m,4H),2.05(m,2H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),1.67(s,6H),1.60(s,3H),1.55(m,2H),1.05(t,3H,J=6.9Hz)IR(KBr,cm-1):2950,2850,1735,1620,1260
元素分析,C37H46O15计算值(%):C 60.82;H 6.30;O 32.88测定值(%):C 60.85;H 6.35;O 32.80化合物1291H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.35~7.15(m,25H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.35~5.20(m,10H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.15(m,3H),2.25(t,2H,J=6.9Hz),1.56(m,2H),1.04(t,3H,J=6.9Hz)IR(KBr,cm-1):2950,2850,1705,1620,1260
元素分析,C54H52O11计算值(%):C 73.97;H 5.94;O 20.09测定值(%):C 73.98;H 5.96;O 20.06化合物1301H-NMR(DMSO-d6,δ-TMS):10.15(s,1H),9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H)5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),3.85(s,1H),3.75~3.20(m,6H)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C15H16O10计算值(%):C 50.56;H 4.53;O 44.91测定值(%):C 50.52;H 4.55;O 44.93化合物1311H-NMR(DMSO-d6,δ-TMS):9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.20(s,3H),3.85(s,1H),3.75~3.20(m,6H)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.83;H 4.85;O 43.32化合物1321H-NMR(DMSO-d6,δ-TMS):9.20(bs,1H),7.55(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.45(t,2H,J=6.4Hz),3.85(s,1H),3.75~3.20(m,6H),1.80~1.30(m,12H),0.87(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2920,2850,1690,1630,1610,1250
元素分析,C23H32O10计算值(%):C 58.96;H 6.89;O 34.15测定值(%):C 58.95;H 6.85;O 34.20化合物1331H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.42(t,2H,J=6.4Hz),3.85(s,1H),3.75~3.20(m,6H),1.80~1.25(m,16H),0.85(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2920,2850,1690,1630,1610,1250
元素分析,C25H36O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.35;H 7.45;O 32.20化合物1341H-NMR(DMSO-d6,δ-TMS):9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.42(t,2H,J=6.4Hz),3.85(s,1H),3.75~3.20(m,6H),1.90~1.25(m,20H),0.85(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2920,2850,1690,1630,1610,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.75;H 7.45;O 30.80化合物1351H-NMR(DMSO-d6,δ-TMS):9.28(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.45(m,1H),3.85(s,1H),3.75-3.10(m,6H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.10;H 5.65;O 40.25化合物1361H-NMR(CDCl3,δ-TMS):9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.99(m,1H),4.85(bs,1H),4.77(bs,1H),3.75~3.20(m,6H),2.20~1.25(m,9H),0.95(d,3H,J=6.7Hz)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.43;H 6.35;O 35.22化合物1371H-NMR(DMSO-d6,δ-TMS):9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),6.45(dd,1H,J=17.5Hz,J=9.5Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.15(dd,1H,J=17.5Hz,J=2.0Hz),3.95(dd,1H,J=9.5Hz,J=2.0Hz),3.85(s,1H),3.75~3.20(m,6H)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.33;H 4.80;O 41.87化合物1381H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1HJ=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.55(m,1H)5.34(m,2H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.27(t,2H,J=6.2Hz),3.85(s,1H),3.75~3.20(m,6H),2.30~1.95(m,4H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.57;H 5.85;O 36.58化合物1391H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.41(m,1H),5.13(m,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),4.12(d,2H,J=8.5Hz),3.85(s,1H),3.75~3.20(m,6H),2.05(m,4H),1.67(s,6H),1.60(s,3H)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.89;H 6.65;O 32.36化合物1401H-NMR(DMSO-d6,δ-TMS):9.15(bs,1H),7.61(d,1H,J=8.8Hz),7.35(m,5H),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.23(s,2H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),3.85(s,1H),3.75~3.20(m,6H)IR(KBr,cm-1):3335,2950,2920,2850,1690,1630,1610,1250
元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.25;H 4.79;O 35.96化合物1411H-NMR(DMSO-d6,δ-TMS):9.25(bs,1H),7.77(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H),4.52(t,1H,J=6.6Hz),4.11(d,2H,J=6.0Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.96(s,3H)IR(KBr,cm-1):2950,1750,1620,1370,1240
元素分析,C25H26O15计算值(%):C 53.00;H 4.59;O 42.41测定值(%):C 52.95;H 4.55;O 42.50化合物1421H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H),4.52(t,1H,J=6.6Hz),4.25(s,3H),4.11(d,2H,J=6.0Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.96(s,3H)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C26H28O15计算值(%):C 53.79;H 4.83;O 41.38测定值(%):C 53.85;H 4.79;O 41.36化合物1431H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.35~7.20(m,20H),7.11(d1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz)5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H)5.30~5.18(m,8H),4.52(t,1H,J=6.6Hz),4.46(t,2H,J=6.0Hz),4.11(d,2H,J=6.0Hz),1.95~1.40(m,16H),2.30(q,2H,J=7.1Hz),1.10(t,3H,J=7.1Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1725,1640,1610,1250
元素分析,C56H64O11计算值(%):C 73.68;H 7.02;O 19.30测定值(%):C 73.65;H 7.05;O 19.30化合物1441H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.35~7.20(m,20H),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H),5.30~5.18(m,8H),4.52(t,1H,J=6.6Hz),4.38(t,2H,J=6.0Hz),4.11(d,2H,J=6.0Hz),2.25(q,2H,J=7.2Hz),1.95~1.40(m,20H),1.10(t,3H,J=7.2Hz),0.93(t,3H,J=6.8Hz)IR(KBr,cm-1):2920,2850,1700,1640,1610,1250
元素分析,C58H68O11计算值(%):C 74.04;H 7.23;O 18.73测定值(%):C 74.08;H 7.35;O 18.57化合物1451H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.40~7.20(m,20H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.30~5.18(m,8H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,4H),2.25(s,3H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):2950,2850,1735,1610,1250
元素分析,C48H48O11计算值(%):C 72.00;H 6.00;O 22.00测定值(%):C 71.95;H 5.96;O 22.09化合物1461H-NMR(CDCl3,δ-TMS):7.77(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H),5.02(m,1H),4.52(t,1H,J=6.6Hz),4.11(d,2H,J=6.0Hz),2.34(s,3H),2.25~1.24(m,9H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.96(s,3H),0.97(d,3H,J=7.0Hz)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C32H38O15计算值(%):C 58.00;H 5.74;O 36.26测定值(%):C 57.95;H 5.79;O 36.26化合物1471H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.11(d,1H,J=2.4Hz),7.05(dd,1H,J=2.4Hz,J=8.8Hz),6.44(dd,1H,J=17.5Hz,J=9.5Hz),5.66(d,1H,J=7.2Hz),5.38(d,1H,J=2.4Hz),5.30~5.20(m,2H),4.52(t,1H,J=6.6Hz),4.20(dd,1H,J=17.5Hz,J=2.0Hz),4.11(d,2H,J=6.0Hz),3.96(dd,1H,J=9.5Hz,J=2.0Hz),2.34(s,3H),2.16(s,3H),2.05(s,3H),2.02(s,3H),1.96(s,3H)IR(KBr,cm-1):2950,2850,1725,1610,1250
元素分析,C27H28O15计算值(%):C 54.73;H 4.73;O 40.54测定值(%):C 54.85;H 4.79;O 40.36化合物1481H-NMR(DMSO-d6,δ-TMS):7.77(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz,7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.34(m,2H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1H,J=9.8Hz),4.40~4.10(m,5H),2.34(s,3H),2.30~1.95(m,4H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):2950,2850,1735,1610,1250
元素分析,C31H36O15计算值(%):C 57.41;H 5.56;O 37.03测定值(%):C 57.45;H 5.59;O 36.96化合物 491H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.11(m,2H),5.04(t,1H,J=9.8Hz),4.40~4.22(m,3H),4.12(d,2H,J=8.5Hz),2.35(m,4H),2.05(m,2H),2.04(s,3H),2.03(s,3H),2.02(s,3H),1.99(s,3H),1.67(s,6H),1.60(s,3H),1.55(m,2H),1.00(t,3H,J=6.8Hz)IR(KBr,cm-1):2950,2850,1735,1620,1260
元素分析,C37H46O15计算值(%):C 60.82;H 6.30;O 32.88测定值(%):C 60.85;H 6.35;O 32.80化合物1501H-NMR(DMSO-d6,δ-TMS):7.65(d,1H,J=8.8Hz),7.35~7.15(m,25H),7.12(d,1H,J=2.4Hz),7.06(dd,1H,J=2.4Hz,J=8.8Hz),5.74(d,1H,J=7.6Hz),5.41(t,1H,J=9.4Hz),5.35~5.20(m,10H),5.13(dd,1H,J=7.6Hz,J=9.6Hz),5.04(t,1HJ=9.8Hz),4.40~4.15(m,3H),2.25(t,2H,J=7.0Hz),1.55(m,2H),1.00(t,3H,J=7.0Hz)IR(KBr,cm-1):2950,2850,1705,1620,1260
元素分析,C54H52O11计算值(%):C 73.97;H 5.94;O 20.09测定值(%):C 73.94;H 5.96;O 20.10化合物1511H-NMR(DMSO-d6,δ-TMS):10.24(bs,1H),9.17(bs,1H),7.61(d,1H,J=8.8Hz),7.12(d,1H,J=2.4Hz),7.07(dd,1H,J=2.2Hz,J=9.0Hz),5.47(s,1H),5.07(bs,1H),4.85(bs,1H),4.77(bs,1H),3.85(s,1H),3.75~3.20(m,6H)IR(KBr,cm-1):3400,2950,2920,2850,1680,1630,1610,1250
元素分析,C15H16O10计算值(%):C 50.56;H 4.53;O 44.91测定值(%):C 50.52;H 4.55;O 44.93化合物1521H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.35(m,5H),7.10~7.00(m,2H),5.28(s,2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),3.65~3.25(m,6H)IR(KBr,cm-1):3330,3300,2950,2850,1700,1620,1260
元素分析,C22H22O10计算值(%):C 59.19;H 4.97;O 35.84测定值(%):C 59.33;H 4.89;O 35.78化合物1531H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.23(s,3H),3.65~3.25(m,6H)IR(KBr,cm-1):3350,2950,2920,2850,1680,1630,1610,1250
元素分析,C16H18O10计算值(%):C 51.89;H 4.90;O 43.21测定值(%):C 51.85;H 4.78;O 43.37化合物1541H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.47(t,2H,J=6.6Hz),3.65~3.25(m,6H),1.80~1.70(m,2H),1.60~1.20(m,14H),0.90(t,3H,J=7.2Hz)IR(KBr,cm-1):3400,2950,2920,2850,1680,1630,1610,1250
元素分析,C25H36O10计算值(%):C 60.47;H 7.31;O 32.22测定值(%):C 60.45;H 7.40;O 32.15化合物1551H-NMR(DMSO-d6,δ-TMS):9.10(bs,1H),7.60(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.65(bs,1H),4.52(bs,1H),4.47(t,2H,J=6.6Hz),3.65~3.25(m,6H),1.80~1.70(m,2H),1.60~1.20(m,18H),0.90(t,3H,J=7.2Hz)IR(KBr,cm-1):3350,2950,2920,2850,1680,1630,1610,1250
元素分析,C27H40O10计算值(%):C 61.81;H 7.69;O 30.50测定值(%):C 61.75;H 7.45;O 30.80化合物1561H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.50(m,2H),3.65~3.25(m,6H),1.05(d,6H,J=7.5Hz)IR(KBr,cm-1):3400,2950,2920,2850,1680,1630,1610,1250
元素分析,C18H22O10计算值(%):C 54.27;H 5.57;O 40.16测定值(%):C 54.07;H 5.67;O 40.26化合物1571H-NMR(CDCl3,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.21(bs,1H),5.00(m,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),3.65~3.25(m,6H),2.20~1.14(m,9H),0.96(d,2H,J=6.8Hz)IR(KBr,cm-1):3350,2950,2920,2850,1680,1630,1610,1250
元素分析,C22H28O10计算值(%):C 58.40;H 6.24;O 35.36测定值(%):C 58.25;H 6.38;O 35.37化合物1581H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),6.45(dd,1H,J=17.5Hz,J=9.5Hz),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.15(dd,1H,J=17.5Hz J=2.0Hz),3.96(dd1H,J=9.5Hz,J=2.0Hz),3.65~3.25(m,6H)IR(KBr,cm-1):3350,2950,2920,2850,1680,1630,1610,1250
元素分析,C17H18O10计算值(%):C 53.40;H 4.75;O 41.85测定值(%):C 53.45;H 4.78;O 41.77化合物1591H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.55(m,1H),5.34(m,1H),5.21(bs,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.27(t,2H,J=6.2Hz),3.65~3.25(m,6H),2.30~1.95(m,4H),0.97(t,3H,J=7.0Hz)IR(KBr,cm-1):3350,2950,2920,1700,1640,1605,1260
元素分析,C21H26O10计算值(%):C 57.53;H 5.98;O 36.49测定值(%):C 57.77;H 5.85;O 36.38化合物1601H-NMR(DMSO-d6,δ-TMS):9.16(bs,1H),7.61(d,1H,J=9.6Hz),7.10~7.00(m,2H),5.40(m,1H),5.21(bs,1H),5.11(m,1H),4.92(d,1H,J=7.6Hz),4.88(bs,1H),4.67(bs,1H),4.52(bs,1H),4.15(d,2H,J=8.5Hz),3.65~3.25(m,6H),2.05(m,4H),1.67(s,6H),1.60(s,3H)IR(KBr,cm-1):3350,2950,2920,1700,1640,1605,1260
元素分析,C25H32O10计算值(%):C 60.96;H 6.55;O 32.49测定值(%):C 60.83;H 6.62;O 32.55试验例1
小鼠的急性毒性试验
我们进行这个试验是为了确定本发明的化合物的安全程度,下面说明急性毒性试验的方法。
方法:将7-糖氧基苯并吡喃衍生物(化合物号:3、8、9、11、15、16、18-23、35、37-47、61-72、75、86-96、99、108-118、130~140、145、151~160)以1000和2000mg/kg的剂量使用食管探子迫使雄性ICR小鼠口服(体重20-25g,每一组5只小鼠)。服用后将动物关在笼子里7天,观察整体症状并统计死去的动物。致死剂量(LD50:mg/kg)是从服用后第七天的死亡率推算。
结果,7-糖氧基苯并吡喃衍生物的LD50超过2000mg/kg,因此明显说明本发明的化合物具有非常低的毒性。试验例2
对大鼠的同源性被动皮肤过敏性反应(PCA)的效果
我们通过PCA反应这个已知筛选抗变应性制剂的试验进行这个药理学试验,它是为了验证本发明的化合物具有抗变应性活性。这种试验动物试样是由速发型变应性反应(即:抗原-抗体反应)引起。下面解释该药理学试验的方法。
方法:将0.05ml抗二硝基苯基化的蛔虫(ascaris)(DNP-As)的抗血清对雄性wistar大鼠(9周令)的两处刮净的脊背皮肤进行皮内给药。48小时后将悬浮在0.5%羧甲基纤维素(CMCNa)中的7-糖氧基苯并吡喃衍生物(试验化合物)以50mg/kg的剂量给动物口服。服用试验化合物一小时后,通过注射1ml溶解有5mg Evans Blue和1mg三硝基苯基化的蛔虫(TNP-As)的盐水入动物尾部静脉以诱发动物的过敏性反应,诱发过敏30分钟后,用乙醚麻醉动物,并放血杀死,剥下脊背皮。根据Katayama等人的方法(Microbiol. Immunol.,Vol.22,89-101,1978)测量渗出的染料。作为载体对照组仅口服0.5%的CMCNa溶液,而作为阳性对照组用与试验化合物组相同的方法,以100mg/kg的剂量给动物口服悬浮在0.5%CMCNa中的安宁(Tranilast)。PCA反应的抑制作用(%)根据公式1计算,所得结果列于表2中,每个试验组包括5只大鼠。(公式1)其中:A:是载体对照组的染料量B:是试验化合物组或阳性对照组的染料量
表2化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物3 53.1 化合物61 40.2化合物8 49.2 化合物62 53.2化合物9 54.5 化合物63 55.7化合物11 43.2 化合物64 54.9化合物15 40.1 化合物65 52.1化合物16 42.3 化合物66 49.3化合物18 42.5 化合物67 50.4化合物19 44.9 化合物68 49.5化合物20 42.3 化合物69 48.1化合物21 45.2 化合物70 51.3化合物22 43.6 化合物71 49.8化合物23 44.7 化合物72 45.2化合物35 42.2 化合物75 45.5化合物37 55.1 化合物86 56.4化合物38 59.3 化合物87 60.3化合物39 62.2 化合物88 61.5化合物40 57.3 化合物89 57.8化合物41 55.4 化合物90 54.3化合物42 56.4 化合物91 55.5化合物43 57.9 化合物92 58.9化合物44 54.5 化合物93 55.2化合物45 55.2 化合物94 53.7化合物46 54.3 化合物95 54.2化合物47 52.1 化合物96 50.1
表2(续)化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物99 40.2 化合物136 42.2化合物108 45.3 化合物137 41.7化合物109 42.1 化合物138 42.5化合物110 41.4 化合物139 41.8化合物111 43.1 化合物140 40.4化合物112 44.5 化合物145 40.2化合物113 40.3 化合物151 45.4化合物114 45.3 化合物152 41.3化合物115 42.2 化合物153 42.4化合物116 46.1 化合物154 43.2化合物117 40.3 化合物155 42.9化合物118 41.2 化合物156 42.1化合物130 40.1 化合物157 48.1化合物131 41.2 化合物158 44.3化合物132 42.9 化合物159 45.1化合物133 42.3 化合物160 43.9化合物134 41.5化合物135 40.3 安宁 54.6
正如表2所示,可以证实本发明的所有化合物具有相当或比安宁更优异的抗变应性活性,这些例子的结果清楚的显示本发明的化合物对速发型变应性疾病是有用的抗变应性药剂。对比试验例1对大鼠的同源性被动皮肤过敏性反应(PCA)的效果
通过PCA反应将本发明化合物的抗变应性活性与专利(WO 92/13852)公开的类似化合物进行对比。这个药理学试验是根据试验例2所述的方法进行,对比化合物列于表3中,结果列于表4中。
表3对比化合物号 化合物名称对比化合物1 4-羟基-3,7-二甲氧基-2H-1-苯并吡喃-2-酮对比化合物2 3-丁氧基-4-羟基-7-甲氧基-2H-1-苯并吡喃-2-酮对比化合物3 3-羟基-4,7-二甲氧基-2H-1-苯并吡喃-2-酮对比化合物4 3-羟基-4-丁氧基-7-甲氧基-2H-1-苯并吡喃-2-酮
表4对比化合物号 抑制作用(%) 本发明化合物号 抑制作用(%)对比化合物1 28.1 化合物3 53.1对比化合物2 32.4 化合物9 54.5化合物37 55.1化合物86 56.4对比化合物3 31.5 化合物109 42.1对比化合物4 26.2 化合物153 42.4化合物110 41.4化合物18 42.5
从试验例2和该对比试验例的结果可以清楚地看出本发明的化合物7-糖基化物的抗变应性活性高于对比化合物。试验例3对小鼠由间三硝基氯苯诱发的接触性皮炎的效果
我们通过已知的试验性接触性皮炎试样进行这个药理学试验以证实本发明的化合物对迟延型过敏的抑制,这个试验动物试样是典型的迟延型过敏模式它主要由细胞免疫响应(Immunology,Vol.15,P.45-416,1968)引起迟延型过敏可由类固醇药物抑制,但是已知的抗变应性药剂对其无效。下面将描述这个药理学试验的方法。
方法:将前一天刮净其腹部皮肤的小鼠用0.1ml含有7mg间三硝基氯苯的丙酮施加到腹部的皮肤上而免疫。免疫7天后,用厚度千分表测量耳朵的厚度,然后通过对左耳朵的每侧皮肤上涂复5μL1%间三硝基氯苯的橄榄油溶液而对小鼠激发,激发后24小时再次测量左耳朵的厚度,并根据公式2计算厚度的增加(%)。悬浮在0.5%的CMCNa中的本发明化合物(试验化合物)以50mg/kg的剂量在激发前1小时和激发后16小时进行强制口服。作为载体对照组,仅仅口服0.5%的CMCNa溶液,作为阳性对照组,用强的松龙、类固醇激素和安宁分别以10mg/kg/和100mg/kg的剂量口服。按照公式2和3计算对载体对照组厚度增加的抑制作用(%),结果列于表5中。(公式2)
增加(%)=(A-B)/B×100其中:A:是激发后24小时的耳朵厚度B:是激发前的耳朵厚度(公式3)抑制作用(%)=(C-D)/C×100其中:C:是载体对照组的增加(%)D:是试验化合物组或阳性对照组的增加(%)
表5化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物3 51.3 化合物61 43.1化合物8 50.3 化合物62 49.3化合物9 52.1 化合物63 53.1化合物11 44.3 化合物64 52.6化合物15 41.2 化合物65 50.3化合物16 43.5 化合物66 51.4化合物18 40.2 化合物67 53.2化合物19 47.1 化合物68 47.3化合物20 45.2 化合物69 49.9化合物21 48.9 化合物70 52.1化合物22 47.3 化合物71 47.4化合物23 49.3 化合物72 42.3化合物35 40.5 化合物75 40.3化合物37 53.9 化合物86 59.4化合物38 63.7 化合物87 64.9化合物39 65.1 化合物88 66.8化合物40 62.1 化合物89 62.3化合物41 60.1 化合物90 60.1化合物42 58.3 化合物91 59.3化合物43 55.4 化合物92 57.2化合物44 56.3 化合物93 56.4化合物45 54.2 化合物94 51.2化合物46 57.6 化合物95 55.8化合物47 51.9 化合物96 48.9
表5(续)化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物99 40.3 化合物136 41.2化合物108 42.4 化合物137 43.5化合物109 43.8 化合物138 44.7化合物110 42.9 化合物139 42.1化合物111 41.2 化合物140 40.1化合物112 43.3 化合物145 42.1化合物113 45.5 化合物151 46.5化合物114 47.3 化合物152 43.2化合物115 40.2 化合物153 44.7化合物116 44.4 化合物154 41.6化合物117 42.3 化合物155 40.9化合物118 43.5 化合物156 43.2化合物130 41.2 化合物157 50.9化合物131 40.9 化合物158 48.2化合物132 43.2 化合物159 44.3化合物133 41.4 化合物160 46.7化合物134 43.7 强的松龙 63.7化合物135 44.6 安宁 4.3
可以清楚地看出试验化合物相对于载体对照组有效地抑制了40%至65%的耳朵肿大,许多本发明化合物相当于或超过强的松龙的作用(抑制作用:63.7%),相反,广泛用于变应性疾病的安宁不能抑制延迟型过敏。这些结果清楚地说明本发明的化合物对于迟延型过敏具有非常好的抑制活性。因此,本发明的化合物是非常有用的抗变应性药剂。试验例4对豚鼠的试验性哮喘试样的效果
哮喘是典型的变应性疾病,我们通过已知的豚鼠的试验性哮喘试样进行这个药理学试验以确证本发明的化合物对哮喘的抑制。下面描述该药理学试验的方法。
方法:雄性hartley豚鼠通过以一周三次腹膜内注射1ml含有5mg卵清蛋白(OVA)的盐水而免疫,最后免疫2周后,通过吸入1分钟的OVA-盐水而使动物激发,激发后,用PULMOS-1(Medical Interf-ace Project Station Inc.)测量动物气道阻力30分钟。将悬浮在0.5%的CMCNa中的本发明化合物(试验化合物)以50mg/kg的剂量口服。作为阳性对照组,用熟知的抗变应性剂色甘酸二钠(Disodi-um Cromoglicate)(DSCG)的盐水溶液按20mg/kg的剂量注射入动物的静脉。作为载体对照组,仅仅口服0.5%的CMCNa溶液。载体对照组的气道阻力抑制(%)根据公式5计算。结果示于表6中,每个试验组包括5只豚鼠。(公式5)
抑制作用=(A-B)/A×100其中:A:是载体对照组的最大气道阻力B:是试验化合物组或阳性对照组的最大气道阻力
表6化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物3 63.1 化合物61 45.2化合物8 59.2 化合物62 50.1化合物9 60.3 化合物63 53.2化合物11 45.7 化合物64 57.2化合物15 42.1 化合物65 49.3化合物16 40.2 化合物66 54.3化合物18 52.3 化合物67 60.2化合物19 65.2 化合物68 63.5化合物20 55.4 化合物69 59.3化合物21 63.1 化合物70 65.6化合物22 60.6 化合物71 63.2化合物23 61.5 化合物72 52.1化合物35 38.2 化合物75 43.5化合物37 68.2 化合物86 73.2化合物38 75.5 化合物87 79.5化合物39 77.8 化合物88 80.2化合物40 73.1 化合物89 77.3化合物41 70.2 化合物90 72.1化合物42 68.5 化合物91 69.5化合物43 70.7 化合物92 65.2化合物44 65.1 化合物93 69.7化合物45 62.3 化合物94 73.2化合物46 63.4 化合物95 63.2化合物47 59.1 化合物96 58.2
表6(续)化合物号 抑制作用(%) 化合物号 抑制作用(%)化合物99 39.2 化合物136 51.2化合物108 50.1 化合物137 45.4化合物109 53.1 化合物138 50.8化合物110 56.5 化合物139 47.2化合物111 61.3 化合物140 45.1化合物112 57.2 化合物145 41.9化合物113 56.6 化合物151 49.7化合物114 59.7 化合物152 52.4化合物115 53.1 化合物153 54.3化合物116 62.8 化合物154 59.2化合物117 49.4 化合物155 57.6化合物118 45.3 化合物156 48.2化合物130 40.2 化合物157 55.7化合物131 42.5 化合物158 42.3化合物132 50.1 化合物159 52.3化合物133 43.2 化合物160 58.9化合物134 45.9化合物135 47.1 DSCG 51.2
正如表6所示,口服本发明化合物抑制了40至80%气道阻力的增加,因此本发明的化合物具有非常高的治疗哮喘的活性。制剂实施例1(5%的粉剂)
化合物43 50mg
乳糖 950mg
1000mg
化合物43的结晶在研钵中研磨,并通过用捣锤粉化混合物以充分混合,得到5%的粉剂。制剂实施例2(5%的粉剂)
化合物154 50mg
乳糖 950mg
1000mg
重复制剂实施例1的方法得到5%的粉剂。制剂实施例3(10%的粒剂)
化合物62 300mg
乳糖 2000mg
淀粉 670mg
明胶 30mg
3000mg
化合物62与同样量的淀粉混合,并在研钵中粉化,然后与乳糖和剩余的淀粉混合。另外,将30mg的明胶与1ml的纯水混合,通过加热溶解、冷却,然后搅拌,与1ml乙醇混合,以制备明胶溶液。此后,上述制备的混合物与明胶溶液混合,所得的混合物然后捏合、造粒、干燥,得到粒剂。制剂实施例4(10%的粒剂)
化合物132 300mg
乳糖 2000mg
淀粉 670mg
明胶 30mg
3000mg
重复制剂实施例3的方法得到10%的粒剂。制剂实施例5(5mg的片剂)
化合物21 5mg
乳糖 62mg
淀粉 30mg
滑 2mg
硬脂酸镁 1mg
100mg/片
使用上述组份20倍的量以制备每片含5mg化合物21的片剂,即100mg的结晶形式的化合物21在研钵中粉化,并与乳糖和淀粉混合,如此制备的制剂与10%的淀粉糊混合,然后捏合该混合物并造粒。干燥后,所得颗粒与滑石和硬脂酸镁混合,并以常规方法制成片剂。
(5mg的片剂)
化合物110 5mg
乳糖 62mg
淀粉 30mg
滑石 2mg
硬脂酸镁 1mg
100mg/片
重复制剂实施例5的方法得到5mg的片剂。制剂实施例7(20mg的片剂)
化合物22 20mg
6%的羟丙基纤维素/乳糖 75mg
硬脂酸盐/滑 2mg
土豆淀粉 3mg
100mg/片
使用上述组份10倍的量以制备每片含20mg活性成份的片剂,即:将6g的羟丙基纤维素溶解在适当体积的乙醇中,并与94g乳糖混合,接着捏合。干燥到一定程度后,该混合物过60目筛,筛过的颗粒用作6%的羟丙基纤维素/乳糖。另外,将硬脂酸镁和滑石以1∶4的比例混合,并用作硬脂酸盐/滑石。此后,将化合物22、6%的羟丙基纤维素/乳糖、硬脂酸盐/滑石和土豆淀粉充分混合,并以常规方法制成片剂。制剂实施例8(20mg的片剂)
化合物87 20mg
6%的羟丙基纤维素/乳糖 75mg
硬脂酸盐/滑石 2mg
土豆淀粉 3mg
100mg/片
重复制剂实施例7的方法得到20mg的药片。制剂实施例9(25mg的片剂)
化合物68 25mg
乳糖 122mg
羧乙基淀粉 50mg
滑石 2mg
硬脂酸镁 1mg
200mg/片
使用比上述组份大10倍的量放入研钵中以制备每片含25mg活性成份的片剂,即把250mg的结晶形式的化合物68在研钵中粉化,并与乳糖充分混合,把适量体积的纯水添加到羧乙基淀粉中,接着将其添加到上述混合物中,所得的混合物捏合并造粒。干燥后,如此所得颗粒与滑石和硬脂酸镁混合,并以常规方法制片。制剂实施例10(25mg的药片)
化合物153 25mg
乳糖 122mg
羧乙基淀粉 50mg
滑石 2mg
硬脂酸镁 1mg
200mg/片
重复制剂实施例9的过程得到25mg的片剂。制剂实施例11(10mg的胶囊)
化合物132 300mg
乳糖 2000mg
淀粉 670mg
明胶 30mg
3000mg
按制剂实施例3的过程制备颗粒,然后以10mg的量装填胶囊。制剂实施例12(10mg的胶囊)
化合物116 300mg
乳糖 2000mg
淀粉 670mg
明胶 30mg
3000mg
重复制剂实施例11的方法得到10mg胶囊。试剂实施例13(0.1%的注射液)
化合物3 10mg
聚乙二醇400 3ml
多乙氧基醚80 0.01ml
注射用蒸馏水 平衡量
10ml
把化合物3溶解在聚乙二醇400和多乙氧基醚80的混合物溶液中,通过逐渐加入注射用蒸馏水而将所得溶液的体积调整到10ml,然后将如此所得的溶液无菌装入安瓿中。试剂实施例14(0.1%的注射液)
化合物18 10mg
聚乙二醇400 3ml
多乙氧基醚80 0.01ml
注射用蒸馏水 平衡量
10ml
重复试剂实施例13的过程得到0.1%的注射液。
因此,显然根据本发明已提供了一种在药物制备中很有用的新的7-糖氧基苯并吡喃衍生物,并且也提供了一种优良的抗变应性药剂,它具有低毒性,可用于治疗或防治速发型和迟延型变应性疾病,尤其是提供了一种对用现有的抗变应性剂不能有效治疗的迟延型变应性疾病具有高活性的抗变应性药剂。
尽管本发明已经详细并参考其具体实施方案进行了说明,但是很显然本领域的熟练专业人员仍可在不脱离其精神和范围的基础上作出各种改变和改进。
Claims (33)
1、由通式(I)代表的7-糖氧基苯并吡喃衍生物及其生理可接受盐,
(1)其中:R1是氢原子、乙酰基、丙酰基、丁酰基、异丁酰基、苯甲酰基、对-甲氧基苯甲酰基、对-甲基苯甲酰基、对-氯苯甲酰基、对-硝基苯甲酰基、甲氧羰基、乙氧羰基、C1-C12的非环烷基、C5-C8环烷基、C2-C10链烯基、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基;
R2是氢原子、C1-C12的非环烷基、C5-C8环烷基、C2-C10链烯基、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基;以及
R3是其羟基被保护的或未被保护的糖基,并选自葡糖基、甘露糖基和半乳糖基,所述的保护基团为选自C2-C4的链烷酰基、C7-C8的芳酰基和C2-C3的烷基羰基的酰基和C7-C8的芳烷基。
2、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中:R2是氢原子、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基。
3、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中:R1是氢原子、乙酰基、丙酰基、丁酰基、异丁酰基、苯甲酰基、对-甲氧基苯甲酰基、对-甲基苯甲酰基、对-氯苯甲酰基、对-硝基苯甲酰基、甲氧羰基、乙氧羰基。
4、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中:R1是氢原子、C1-C12的非环烷基、C5-C8环烷基或C2-C10链烯基,R2是氢原子、C1-C12的非环烷基、C5-C8环烷基或C2-C10链烯基。
5、权利要求1至3之一的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R1为乙酰基、丙酰基、丁酰基、异丁酰基、苄基;R2为苄基。
6、权利要求1、2或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中:R1是具有1至12个碳原子的非环烷基。
7、权利要求1、2或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R1是具有5至8个碳原子的环烷基。
8、权利要求1、2或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R1是具有2至10个碳原子的链烯基。
9、权利要求4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R1是具有1至12个碳原子的非环烷基、具有5至8个碳原子的环烷基或具有2至10个碳原子的链烯基,R2是氢原子。
10、权利要求1、3或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R2是具有1至12个碳原子的非环烷基。
11、权利要求1、3或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R2是具有5至8个碳原子的环烷基。
12、权利要求1、3或4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R2是具有2至10个碳原子的链烯基。
13、权利要求4的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R1是氢原子,R2是具有1至12个碳原子的非环烷基、具有5至8个碳原子的环烷基或具有2至10个碳原子的链烯基。
14、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R3是葡糖基。
15、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R3是甘露糖基。
16、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R3是半乳糖基。
17、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R3是未保护的糖基。
18、权利要求1的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中R3是用所述的酰基或芳烷基保护的糖基。
19、权利要求18的7-糖氧基苯并吡喃衍生物及其生理可接受盐,其中所述的酰基或芳烷基为乙酰基、丙酰基、丁酰基、异丁酰基、苯甲酰基、对-甲氧基苯甲酰基、对-甲基苯甲酰基、对-氯苯甲酰基、对-硝基苯甲酰基、甲氧羰基、乙氧羰基、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基。
20、一种抗变应性组合物,包括治疗上有效量的通式(I)化合物或其生理可接受盐,及药物上可接受的载体,
(1)其中:R1是氢原子、乙酰基、丙酰基、丁酰基、异丁酰基、苯甲酰基、对-甲氧基苯甲酰基、对-甲基苯甲酰基、对-氯苯甲酰基、对-硝基苯甲酰基、甲氧羰基、乙氧羰基、C1-C12的非环烷基、C5-C8环烷基、C2-C10链烯基、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基;
R2是氢原子、C1-C12的非环烷基、C5-C8环烷基、C2-C10链烯基、苄基、对-甲氧基苄基、对-甲基苄基、对-氯苄基或对-硝基苄基;以及
R3是其羟基被保护的或未被保护的糖基,并选自葡糖基、甘露糖基和半乳糖基,所述的保护基团为选自C2-C4的链烷酰基、C7-C8的芳酰基和C2-C3的烷基羰基的酰基和C7-C8的芳烷基。
21、权利要求20的抗变应性组合物,其中R1是氢原子、C1-C12非环烷基、C5-C8环烷基或C2-C10链烯基,和R2是氢原子、C1-C12非环烷基、C5-C8环烷基或C2-C10链烯基。
22、权利要求21的抗变应性组合物,其中R1是具有1至12个碳原子的非环烷基、具有5至8个碳原子的环烷基或具有2至10个碳原子的链烯基。
23、权利要求21的抗变应性组合物,其中R1是氢原子,而R2是C1-C12非环烷基、C5-C8环烷基或C2-C10链烯基。
24、权利要求21的抗变应性组合物,其中R1是C1-C12非环烷基、C5-C8环烷基或C2-C10链烯基,而R2是氢原子。
25、权利要求24的抗变应性组合物,其中R1是具有1至12个碳原子的非环烷基。
26、权利要求24的抗变应性组合物,其中R1是具有5至8个碳原子的环烷基。
27、权利要求24的抗变应性组合物,其中R1是具有2至10个碳原子的链烯基。
28、权利要求20至27之一的抗变应性组合物,其中R3是葡糖基。
29、权利要求20至27之一的抗变应性组合物,其中R3是甘露糖基。
30、权利要求20至27之一的抗变应性组合物,其中R3是半乳糖基。
31、权利要求20至27之一的抗变应性组合物,其中R3是未保护的糖基。
32、权利要求20至27之一的抗变应性组合物,其中R3是用所述的酰基或芳烷基保护的糖基。
33、权利要求1所述的通式(I)化合物或其生理上可接受盐在制备治疗变应性疾病的药剂中的应用。
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BE586723A (fr) * | 1960-01-19 | 1960-07-19 | Sarec S A | Nouveaux composes chimiques et thérapeutiques dérives des isoflavones, et leurs procédés de préparation. |
FR1445465A (fr) * | 1964-08-12 | 1966-07-15 | Robert & Carriere Lab | Dérivés de la rutine et leur préparation |
BE803359A (fr) * | 1972-08-31 | 1973-12-03 | Cortial | Nouveaux derives de la quercetine et leur procede de preparation |
PT68117A (fr) * | 1977-06-02 | 1978-06-01 | Sarget Lab | Nouveau procede de preparation de derives de glycosides benzopyranniques |
EP0646591B1 (en) * | 1993-09-28 | 1996-07-31 | Dainippon Ink And Chemicals, Inc. | 3- Or 4-glycosyloxybenzopyran derivative and antiallergic agent containing the derivative as active ingredient |
-
1995
- 1995-03-22 JP JP06264695A patent/JP3831953B2/ja not_active Expired - Fee Related
- 1995-05-19 US US08/446,115 patent/US5580552A/en not_active Expired - Fee Related
- 1995-05-19 CA CA002149826A patent/CA2149826C/en not_active Expired - Fee Related
- 1995-05-22 AT AT95107805T patent/ATE196910T1/de not_active IP Right Cessation
- 1995-05-22 EP EP95107805A patent/EP0684255B1/en not_active Expired - Lifetime
- 1995-05-22 DE DE69519053T patent/DE69519053T2/de not_active Expired - Fee Related
- 1995-05-23 KR KR1019950012814A patent/KR100355131B1/ko not_active IP Right Cessation
- 1995-05-23 TW TW084105317A patent/TW323283B/zh active
- 1995-05-23 AU AU20252/95A patent/AU682946B2/en not_active Ceased
- 1995-05-23 CN CN95107126A patent/CN1050364C/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4845121A (en) * | 1986-06-13 | 1989-07-04 | The Ohio State University Research Foundation | Aci-reductone compounds belonging to the 6,7-disubstituted-3,4-dihydro benzopyan-2H-one class having antiaggregatory properties |
EP0598117A1 (en) * | 1991-01-31 | 1994-05-25 | Dainippon Ink And Chemicals, Inc. | Benzopyran derivative and antiallergic agent containing the same as active ingredient |
Also Published As
Publication number | Publication date |
---|---|
KR100355131B1 (ko) | 2003-02-05 |
KR950032264A (ko) | 1995-12-20 |
EP0684255A1 (en) | 1995-11-29 |
DE69519053T2 (de) | 2001-03-08 |
US5580552A (en) | 1996-12-03 |
JPH08198890A (ja) | 1996-08-06 |
CA2149826A1 (en) | 1995-11-24 |
ATE196910T1 (de) | 2000-10-15 |
EP0684255B1 (en) | 2000-10-11 |
AU682946B2 (en) | 1997-10-23 |
AU2025295A (en) | 1995-11-30 |
JP3831953B2 (ja) | 2006-10-11 |
CN1124738A (zh) | 1996-06-19 |
CA2149826C (en) | 2005-03-15 |
TW323283B (zh) | 1997-12-21 |
DE69519053D1 (de) | 2000-11-16 |
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