CN111039910A - 一种光引发的合成3-芳基黄酮或香豆素类化合物的方法及应用 - Google Patents
一种光引发的合成3-芳基黄酮或香豆素类化合物的方法及应用 Download PDFInfo
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- CN111039910A CN111039910A CN201911417624.2A CN201911417624A CN111039910A CN 111039910 A CN111039910 A CN 111039910A CN 201911417624 A CN201911417624 A CN 201911417624A CN 111039910 A CN111039910 A CN 111039910A
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- flavone
- hydroxide
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- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 26
- 229930003944 flavone Natural products 0.000 title claims abstract description 25
- 235000011949 flavones Nutrition 0.000 title claims abstract description 25
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title claims abstract description 23
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- 238000000034 method Methods 0.000 title claims abstract description 18
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
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- 125000003277 amino group Chemical group 0.000 claims description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
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- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 6
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- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
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Abstract
本发明涉及一种光引发的合成3‑芳基黄酮或香豆素类化合物的方法及应用,该合成方法为,将黄酮类物质在碱性条件下被可见光激发,与芳基卤化物发生单子转移反应引发自由基,一步生成3‑芳基黄酮衍生物。本发明通过利用黄酮和香豆素类化合物在碱性条件下的光反应活性,通过光激发的黄酮或香豆素类化合物与芳基卤化物之间发生单电子转移反应引发自由基,一步法合成3‑芳基黄酮或香豆素类化合物,方法简单、高效,原料和试剂便宜易得,反应产率高,副产物少,反应的化学和区域选择性高。
Description
技术领域
本发明属于化学合成方法领域,具体涉及一种光引发的合成3-芳基黄酮和香豆素类化合物的方法技术领域。
背景技术
黄酮和香豆素是两类重要的天然产物,不仅数量众多,结构复杂,而且具有许多重要的药理活性,如抗氧化、抗癌、抗菌、抗病毒、抗凝血、光敏活性等。然而黄酮和香豆素类天然产物存在溶解性差、生物利用度不高等缺点限制其药物研究中应用。因此对自然界含量较高的黄酮和香豆素类天然产物进行结构修饰,使之达到成药要求,是合理开发利用黄酮和香豆素类天然产物的一条重要途径。
由于电子效应和空间位阻效应,针对两类天然产物的C-3位定点结构修饰的难度非常大,无法直接利用分离得到的黄酮和香豆素类化合物进行结构修饰,而只能通过化学合成的方法,在起始阶段就在该位置预先引入需修饰的官能团,对每一个分子需要设计一种单独的化学合成路线,因此合成效率非常低。我们发展的新型光反应,利用黄酮和香豆素类化合物在碱性条件下的光反应活性,可以实现两类天然产物C-3位的直接定点结构修饰,经过一步反应制备相应的芳基衍生物,对黄酮和香豆素类天然产物的药用开发具有重要的价值。
发明内容
本发明针对现有技术存在的上述不足之处,本发明提供了一种简洁、高效的光引发的合成3-芳基黄酮和香豆素类化合物的方法,该方法以黄酮和香豆素类化合物为原料,在碱和光的作用下与芳基卤化物发生单电子转移反应,一步法生成一系列3-芳基黄酮和香豆素类化合物。
即以黄酮或香豆素物质为原料,在碱和光的作用下与芳基卤化物发生单电子转移反应引发自由基,一步法生成一系列3-芳基黄酮和香豆素类衍生物。采用该方法合成的3-芳基黄酮和香豆素类衍生物在心脑血管方面的活性有显著的增强。所合成的各种3-芳基黄酮类衍生物具有舒张血管、调节血脂的作用,可应用于高血压、高血脂、粥样动脉硬化、以及脂肪肝等疾病的治疗和预防;所合成的各种3-芳基7-羟基香豆素化合物都含有广泛的共轭体系。电子离域范围很大,在365nm波长下具有强烈的蓝色荧光,甚至在可见光下也可辨认,加碱后可变为绿色荧光,可以用作生物荧光探针、荧光指示剂和酸碱指示剂(pH为6.5-8.0)。
本发明采用如下技术方案实现。
一种3-芳基黄酮衍生物,本发明所述的3-芳基黄酮衍生物化学式为:
3-芳基黄酮衍生物合成方法为,本发明将黄酮类物质在碱性条件下被可见光激发,与芳基卤化物发生单子转移反应引发自由基,一步生成3-芳基黄酮衍生物。
3-芳基黄酮衍生物的合成方法,本发明该合成方法为,具体步骤如下:
(1)将黄酮类物质和芳基卤化物、碱、溶于溶剂中,将所得到的溶液在氮气氛围、-50℃~100℃、300nm~700nm照射下进行反应;黄酮类物质、芳基卤化物与碱的质量比为1:0.5~20:0.5~20。
(2)待步骤(1)反应完全后,加稀盐酸(1N)淬灭后用乙酸乙酯萃取,依次用水、饱和氯化钠水溶液洗,无水硫酸钠干燥后浓缩柱层析,得到3-芳基黄酮衍生物;
其化学反应式为:
Ar选自苯、萘、蒽、菲、芴、吡啶、喹啉、异喹啉、吲哚、吡咯、吡嗪、嘧啶、呋喃、苯并呋喃、苯并噻唑、苯并噻吩或咔唑;
X选自氯、溴或碘;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14相同或不同,其各自选自氢、低级烷基、烯基、炔基、芳基、卤素、羟基、巯基、硝基、氰基、羧基、酯基、醛基、酰基、酰氧基、胺基、取代胺基或酰胺基。
本发明3-芳基黄酮衍生物的应用:用于高血压、高血脂、粥样动脉硬化以及脂肪肝疾病的治疗和预防。
一种3-芳基香豆素衍生物,本发明所述的3-芳基香豆素衍生物化学式为:
3-芳基香豆素衍生物的合成方法,本发明将香豆素类物质在碱性条件下被可见光激发,与芳基卤化物发生单子转移反应引发自由基,一步生成3-芳基香豆素衍生物。
本发明该合成方法为,具体步骤如下:
(1)将香豆素类物质和芳基卤化物、碱、溶于溶剂中,将所得到的溶液在氮气氛围、-50℃~100℃、300nm~700nm照射下进行反应;香豆素类物质、芳基卤化物与碱的质量比为1:0.5~20:0.5~20。
(2)待步骤(1)反应完全后,加稀盐酸(1N)淬灭后用乙酸乙酯萃取,依次用水、饱和氯化钠水溶液洗,无水硫酸钠干燥后浓缩柱层析,得到3-芳基香豆素衍生物;
其化学反应式为:
Ar选自苯、萘、蒽、菲、芴、吡啶、喹啉、异喹啉、吲哚、吡咯、吡嗪、嘧啶、呋喃、苯并呋喃、苯并噻唑、苯并噻吩或咔唑;
X选自氯、溴或碘;
R10、R11、R12、R13、R14、R1'、R2'、R3'、R4'、R5'相同或不同,其各自选自氢、低级烷基、烯基、炔基、芳基、卤素、羟基、巯基、硝基、氰基、羧基、酯基、醛基、酰基、酰氧基、胺基、取代胺基或酰胺基。
本发明3-芳基香豆素衍生物的应用:用作生物荧光探针、荧光指示剂和酸碱指示剂。(pH为6.5-8.0)
进一步为,本发明所述的碱为碳酸氢钠、碳酸氢钾、碳酸氢铯、碳酸氢铵、碳酸锂、碳酸钠、碳酸钾、碳酸铯、碳酸铷、碳酸铵、三乙基甲基甲基碳酸铵、三丁基甲基甲基碳酸铵、磷酸钾、磷酸钠、氢氧化锂、磷酸氢二钾、磷酸氢二钠、氢氧化钠、氢氧化钾、氢氧化铷、氢氧化铯、氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、三丁基苄基氢氧化铵、甲醇钠、甲醇钾、叔丁醇钠、叔丁醇钾、吡啶、2,6-二甲基吡啶、2,6-二叔丁基吡啶、2,4,6-三甲基吡啶、4-二甲氨基吡啶、三乙胺、三甲胺、二异丙基乙基胺、1,4-二氮杂二环[2.2.2]辛烷、1,8-二氮杂二环[5.4.0]十一碳-7-烯、四甲基胍、三乙烯二胺、四甲基乙二胺、N-甲基吗啉或N,N,N',N”,N”-五甲基二亚乙基三胺任一。
进一步为,本发明所述的溶剂为正己烷、环己烷、庚烷、苯、甲苯、二甲苯、三甲苯、三氟甲苯、氯苯、四氯化碳、氯仿、二氯甲烷、1,2-二氯乙烷、四氢呋喃、乙醚、汽油、二硫化碳、氯丙烷、溴乙烷、异丙醚、硝基甲烷、乙酸丁酯、正戊烷、二氧六环、乙酸甲酯、甲基叔丁基醚、石油醚、丙酮、乙腈、甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、叔丁醇、水、吡啶、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、乙酸乙酯、三氟乙醇或六氟异丙醇任一。
本发明的有益效果为,本发明通过利用黄酮和香豆素类化合物在碱性条件下的光反应活性,通过光激发的黄酮或香豆素类化合物与芳基卤化物之间发生单电子转移反应引发自由基,一步法合成3-芳基黄酮或香豆素类化合物,方法简单、高效,原料和试剂便宜易得,反应产率高,副产物少,反应的化学和区域选择性高。本发明所合成的各种3-芳基黄酮类化合物具有舒张血管、调节血脂的作用,可应用于高血压、高血脂、粥样动脉硬化、以及脂肪肝等疾病的治疗和预防;本发明所合成的各种3-芳基香豆素衍生物【3-芳基7-羟基香豆素化合物】都含有广泛的共轭体系。电子离域范围很大,在365nm波长下具有强烈的蓝色荧光,甚至在可见光下也可辨认,加碱后可变为绿色荧光,可以用作生物荧光探针、荧光指示剂和酸碱指示剂(pH为6.5-8.0)。
下面结合附图和具体实施方式本发明做进一步解释。
附图说明
图1为本发明3-芳基黄酮衍生物化学反应式图。
图2为本发明3-芳基香豆素衍生物化学反应式图。
具体实施方式
下面结合附图和实施例对本发明作进一步详细说明,但本发明保护范围不局限于所述内容,
实施例中使用的试剂和方法,如无特殊说明,均采用常规试剂和使用常规方法。
实施例1:
在氮气的氛围下,将3',4'-二羟基黄酮(0.1毫摩尔)、碘苯(0.1毫摩尔)、碳酸铯(0.2毫摩尔)溶于二甲基亚砜(1毫升)中,加毕后将反应物置于25℃的条件下,在450nm光下照射反应26小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(26.4毫克,80%产率)。
实施例2:
在氮气的氛围下,将5,4'-二羟基黄酮(0.1毫摩尔)、对溴苯乙酮(0.3毫摩尔)、碳酸钾(0.5毫摩尔)溶于N,N-二甲基甲酰胺(1毫升)中,加毕后将反应物置于50℃的条件下,在390nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(31.6毫克,85%产率)。
实施例3:
在氮气的氛围下,将4'-羟基-6-甲基黄酮(0.1毫摩尔)、间氯苯腈(0.5毫摩尔)、碳酸氢钾(0.4毫摩尔)溶于N,N-二甲基乙酰胺(1毫升)中,加毕后将反应物置于0℃的条件下,在410nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(27.5毫克,78%产率)。
实施例4:
在氮气的氛围下,将芹菜素(0.1毫摩尔)、邻甲氧基碘苯(0.09毫摩尔)、叔丁醇钾(0.4毫摩尔)溶于乙腈(1毫升)中,加毕后将反应物置于-25℃的条件下,在470nm下照射反应36小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(26.3毫克,70%产率)。
实施例5:
在氮气的氛围下,将野黄芩素(0.1毫摩尔)、2-碘萘(0.3毫摩尔)、三乙胺(0.3毫摩尔)溶于丙酮(1毫升)中,加毕后将反应物置于25℃的条件下,在365nm下照射反应36小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(33.0毫克,80%产率)。
实施例6:
在氮气的氛围下,将木犀草素(0.1毫摩尔)、5-碘吲哚(0.1毫摩尔)、碳酸铵(0.6毫摩尔)溶于乙酸乙酯(1毫升)中,加毕后将反应物置于25℃的条件下,在560nm下照射反应40小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(26.0毫克,65%产率)。
实施例7:
在氮气的氛围下,将4',5-二羟基-7-甲氧基黄酮(0.1毫摩尔)、5-溴苯并呋喃(0.1毫摩尔)、1,4-二氮杂二环[2.2.2]辛烷(0.3毫摩尔)溶于四氢呋喃(1毫升)中,加毕后将反应物置于40℃的条件下,在650nm下照射反应50小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(24.8毫克,62%产率)。
实施例8:
在氮气的氛围下,将柯因(0.1毫摩尔)、碘噻吩(0.4毫摩尔)、四甲基胍(0.2毫摩尔)溶于二氯甲烷(1毫升)中,加毕后将反应物置于0℃的条件下,在500nm下照射反应60小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(24.7毫克,60%产率)。
实施例9:
在氮气的氛围下,将牡荆素(0.1毫摩尔)、3-碘吡啶(0.1毫摩尔)、1,8-二氮杂二环[5.4.0]十一碳-7-烯(0.2毫摩尔)溶于氯仿(1毫升)中,加毕后将反应物置于25℃的条件下,在550nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(36.6毫克,72%产率)。
实施例10:
在氮气的氛围下,将野黄芩苷(0.1毫摩尔)、6-溴喹啉(0.1毫摩尔)、4-二甲氨基吡啶(0.2毫摩尔)溶于乙醇(1毫升)中,加毕后将反应物置于25℃的条件下,在480nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(44.1毫克,75%产率)。
实施例11:
在氮气的氛围下,将木犀草苷(0.1毫摩尔)、4-溴异喹啉(0.2毫摩尔)、二异丙基乙基胺(0.5毫摩尔)溶于三氟乙醇(1毫升)中,加毕后将反应物置于25℃的条件下,在可见光下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(57.5毫克,80%产率)。
实施例12:
在氮气的氛围下,将异荭草苷(0.1毫摩尔)、2-碘吡嗪(0.4毫摩尔)、氢氧化钾(0.2毫摩尔)溶于水(1毫升)中,加毕后将反应物置于50℃的条件下,在310nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(34.7毫克,66%产率)。
实施例13:
在氮气的氛围下,将野黄芩苷甲酯(0.1毫摩尔)、2-碘嘧啶(0.2毫摩尔)、碳酸钠(0.1毫摩尔)溶于甲醇(1毫升)中,加毕后将反应物置于40℃的条件下,在600nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(39.3毫克,71%产率)。
实施例14:
在氮气的氛围下,将当药黄素(0.1毫摩尔)、5-溴-1-茚满酮(0.1毫摩尔)、2,6-二叔丁基吡啶(0.4毫摩尔)溶于异丙醇(1毫升)中,加毕后将反应物置于30℃的条件下,在400nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基黄酮衍生物(43.2毫克,75%产率)。
实施例15:
在氮气的氛围下,将7-羟基香豆素(0.1毫摩尔)、对碘苯甲醛(0.1毫摩尔)、磷酸钾(0.1毫摩尔)溶于三氟甲苯(1毫升)中,加毕后将反应物置于25℃的条件下,在630nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(22.6毫克,85%产率)。
实施例16:
在氮气的氛围下,将6,7-二羟基香豆(0.1毫摩尔)、2-溴蒽(0.4毫摩尔)、碳酸氢铯(0.2毫摩尔)溶于甲苯(1毫升)中,加毕后将反应物置于40℃的条件下,在430nm下照射反应30小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(27.2毫克,77%产率)。
实施例17:
在氮气的氛围下,将瑞香素(0.1毫摩尔)、3-碘-9H-咔唑(0.1毫摩尔)、四丁基氢氧化铵(0.3毫摩尔)溶于乙醚(1毫升)中,加毕后将反应物置于50℃的条件下,在530nm下照射反应36小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(20.6毫克,60%产率)。
实施例18:
在氮气的氛围下,将4-甲基伞形酮(0.1毫摩尔)、对碘苯丙酸(0.4毫摩尔)、碳酸铷(0.5毫摩尔)溶于甲基叔丁基醚(1毫升)中,加毕后将反应物置于-10℃的条件下,在420nm下照射反应32小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(25.9毫克,80%产率)。
实施例19:
在氮气的氛围下,将7-羟基香豆素-4-乙酸(0.1毫摩尔)、间碘苯酚(0.3毫摩尔)、氢氧化铯(0.6毫摩尔)溶于1,2-二氯乙烷(1毫升)中,加毕后将反应物置于10℃的条件下,在450nm下照射反应50小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(18.7毫克,60%产率)。
实施例20:
在氮气的氛围下,将七叶灵倍半水合物(0.1毫摩尔)、3-乙酰基-5-溴吡啶(0.1毫摩尔)、磷酸氢二钾(0.2毫摩尔)溶于六氟异丙醇(1毫升)中,加毕后将反应物置于25℃的条件下,在500nm下照射反应16小时,用稀盐酸(1N)淬灭反应,水相用乙酸乙酯萃取三次(15毫升×3),合并有机相,依次用水、饱和食盐水洗,无水硫酸钠干燥,浓缩后柱层析,得到3-芳基香豆素衍生物(36.7毫克,80%产率)。
实施例21:
所合成的各种3-芳基黄酮类物质具有舒张血管的作用。
迅速取出大鼠胸主动脉,将血管剪成3-4mm的血管环。将血管环转至盛有5mLkrebs液,恒温37℃,持续通混合氧气的浴槽中,将其固定在浴槽内的挂钩上,另一支挂钩与张力换能器连接,用RM-6240系统记录血管环的张力。给予KCl(60mmol/L)诱发内皮完整的大鼠胸主动脉收缩,记录30min药物对血管的舒张作用,若化合物表现出明显的血管舒张作用,则记录时间延长为1小时。给予化合物30min及1h后,化合物4、7、9、10、12对KCl预收缩的大鼠胸主动脉表现出明显而且缓慢的舒张,与阳性对照硝苯地平相比,具有降压平缓持久的特点,更符合临床的实际应用。结果如下表所示。
实施例22:
所合成的各种3-芳基黄酮类物质具有调节血脂的作用。
本实验采用油酸作用于体外培养的人正常肝细胞株HL7702的方式,建立高脂细胞模型,以苯扎贝特作为阳性对照,结合细胞内甘油三脂(TG)的含量,评价化合物对脂肪变性肝细胞的作用。与高脂模型组相比,化合物4、7、9、10、12作用的细胞内甘油三脂(TG)含量都显著减少,与阳性对照药苯扎贝特的降甘油三脂效果相似。结果如下表所示。
以上所述的仅是本发明的部分具体实施例(由于本发明的配方属于数值范围,故实施例不能穷举,本发明所记载的保护范围以本发明的数值范围和其他技术要点范围为准),方案中公知的具体内容或常识在此未作过多描述。应当指出,上述实施例不以任何方式限制本发明,对于本领域的技术人员来说,凡是采用等同替换或等效变换的方式获得的技术方案均落在本发明的保护范围内。本申请要求的保护范围应当以其权利要求的内容为准,说明书中的具体实施方式等记载可以用于解释权利要求的内容。
Claims (10)
2.根据权利要求1所述的3-芳基黄酮衍生物的合成方法,其特征在于:该合成方法为,将黄酮类物质在碱性条件下被可见光激发,与芳基卤化物发生单子转移反应引发自由基,一步生成3-芳基黄酮衍生物。
3.根据权利要求2所述的3-芳基黄酮衍生物的合成方法,其特征在于:该合成方法为,具体步骤如下:
(1)将黄酮类物质和芳基卤化物、碱、溶于溶剂中,将所得到的溶液在氮气氛围、-50℃~100℃、300nm~700nm照射下进行反应;
(2)待步骤(1)反应完全后,加稀盐酸淬灭后用乙酸乙酯萃取,依次用水、饱和氯化钠水溶液洗,无水硫酸钠干燥后浓缩柱层析,得到3-芳基黄酮衍生物;其化学反应式为:
Ar选自苯、萘、蒽、菲、芴、吡啶、喹啉、异喹啉、吲哚、吡咯、吡嗪、嘧啶、呋喃、苯并呋喃、苯并噻唑、苯并噻吩或咔唑;
X选自氯、溴或碘;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14相同或不同,其各自选自氢、低级烷基、烯基、炔基、芳基、卤素、羟基、巯基、硝基、氰基、羧基、酯基、醛基、酰基、酰氧基、胺基、取代胺基或酰胺基。
4.如权利要求1或2或3所述的3-芳基黄酮化合物的应用,其特征在于:用于高血压、高血脂、粥样动脉硬化以及脂肪肝疾病的治疗和预防。
6.根据权利要求5所述的3-芳基香豆素衍生物的合成方法,其特征在于:该合成方法为,将香豆素类物质在碱性条件下被可见光激发,与芳基卤化物发生单子转移反应引发自由基,一步生成3-芳基香豆素衍生物。
7.根据权利要求6所述的3-芳基香豆素衍生物的合成方法,其特征在于:该合成方法为,具体步骤如下:
(1)将香豆素类物质和芳基卤化物、碱、溶于溶剂中,将所得到的溶液在氮气氛围、-50℃~100℃、300nm~700nm照射下进行反应;
(2)待步骤(1)反应完全后,加稀盐酸淬灭后用乙酸乙酯萃取,依次用水、饱和氯化钠水溶液洗,无水硫酸钠干燥后浓缩柱层析,得到3-芳基香豆素衍生物;
其化学反应式为:
Ar选自苯、萘、蒽、菲、芴、吡啶、喹啉、异喹啉、吲哚、吡咯、吡嗪、嘧啶、呋喃、苯并呋喃、苯并噻唑、苯并噻吩或咔唑;
X选自氯、溴或碘;
R10、R11、R12、R13、R14、R1'、R2'、R3'、R4'、R5'相同或不同,其各自选自氢、低级烷基、烯基、炔基、芳基、卤素、羟基、巯基、硝基、氰基、羧基、酯基、醛基、酰基、酰氧基、胺基、取代胺基或酰胺基。
8.如权利要求5或6或7所述的3-芳基香豆素衍生物的应用,其特征在于:用作生物荧光探针、荧光指示剂和酸碱指示剂。
9.根据权利要求3或7所述的合成方法,其特征在于:所述的碱为碳酸氢钠、碳酸氢钾、碳酸氢铯、碳酸氢铵、碳酸锂、碳酸钠、碳酸钾、碳酸铯、碳酸铷、碳酸铵、三乙基甲基甲基碳酸铵、三丁基甲基甲基碳酸铵、磷酸钾、磷酸钠、氢氧化锂、磷酸氢二钾、磷酸氢二钠、氢氧化钠、氢氧化钾、氢氧化铷、氢氧化铯、氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、三丁基苄基氢氧化铵、甲醇钠、甲醇钾、叔丁醇钠、叔丁醇钾、吡啶、2,6-二甲基吡啶、2,6-二叔丁基吡啶、2,4,6-三甲基吡啶、4-二甲氨基吡啶、三乙胺、三甲胺、二异丙基乙基胺、1,4-二氮杂二环[2.2.2]辛烷、1,8-二氮杂二环[5.4.0]十一碳-7-烯、四甲基胍、三乙烯二胺、四甲基乙二胺、N-甲基吗啉或N,N,N',N”,N”-五甲基二亚乙基三胺任一。
10.根据权利要求3或7所述的合成方法,其特征在于:所述的溶剂为正己烷、环己烷、庚烷、苯、甲苯、二甲苯、三甲苯、三氟甲苯、氯苯、四氯化碳、氯仿、二氯甲烷、1,2-二氯乙烷、四氢呋喃、乙醚、汽油、二硫化碳、氯丙烷、溴乙烷、异丙醚、硝基甲烷、乙酸丁酯、正戊烷、二氧六环、乙酸甲酯、甲基叔丁基醚、石油醚、丙酮、乙腈、甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、叔丁醇、水、吡啶、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、乙酸乙酯、三氟乙醇或六氟异丙醇任一。
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