CN106231901A - 作为杀真菌剂的金属酶抑制剂化合物 - Google Patents
作为杀真菌剂的金属酶抑制剂化合物 Download PDFInfo
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- CN106231901A CN106231901A CN201580021710.5A CN201580021710A CN106231901A CN 106231901 A CN106231901 A CN 106231901A CN 201580021710 A CN201580021710 A CN 201580021710A CN 106231901 A CN106231901 A CN 106231901A
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000011276 wood tar Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明描述具有金属酶调节活性的式I化合物,以及通过这样的金属酶治疗疾病、病症或其症状的方法。
Description
相关申请的交叉引用
本申请要求在2014年4月15日提交的美国临时专利申请序列号61/979,543和在2014年9月8日提交的62/047,368的权益,其公开内容明确通过参考并入本申请。
背景技术和发明内容
杀真菌剂是用于防治(protect and/or cure)植物免受农业相关真菌造成的破坏的天然来源或合成来源的化合物。一般来讲,没有单一的杀真菌剂可用在所有情况中。因此,正在研究生产具有更好性能、更易使用和成本更低的杀真菌剂。
本申请涉及金属酶抑制剂以及它们作为杀真菌剂的用途。本申请的化合物可以提供对抗子囊菌(ascomycetes),担子菌(basidiomycetes),半知菌(deuteromycetes),和卵菌(oomycetes)的保护。
本申请的一种实施方式可以包括式I的化合物:
其中:
Z是任选取代的5-嘧啶基,任选取代的4-嘧啶基,任选取代的噻唑基,任选取代的唑基,任选取代的3-吡啶基,或任选取代的4-吡啶基;
n为0或1;
R1是脂族饱和烃基,卤代脂族饱和烃基,芳基,或杂芳基,它们各自任选取代有0个、1个、2个或3个独立的R4;
R2是芳基,杂芳基芳氧基,杂芳氧基,芳基炔基,杂芳基炔基,芳基脂族饱和烃基,杂芳基脂族饱和烃基,芳基脂族饱和烃基氧基,杂芳基脂族饱和烃基氧基,芳氧基脂族饱和烃基,或杂芳氧基脂族饱和烃基,其中各芳基或杂芳基任选取代有0个、1个、2个或3个独立的R4;
R3独立地为H,脂族饱和烃基,芳基,取代的芳基,杂芳基,芳基脂族饱和烃基,或杂芳基脂族饱和烃基,-C(O)脂族饱和烃基,-C(O)芳基,-Si(脂族饱和烃基)3,它们各自任选取代有0个、1个、2个或3个独立的R4;
R4独立地为芳基,杂芳基,脂族饱和烃基,硫代脂族饱和烃基,氰基,卤代脂族饱和烃基,氰基脂族饱和烃基,羟基,脂族饱和烃基氧基,卤素,卤代脂族饱和烃基氧基,-C(O)脂族饱和烃基,-C(O)OH,-C(O)O脂族饱和烃基,-SCF3,-SF5,-SCN,或SO2(芳基);和
R5-R7独立地选自H,脂族饱和烃基,脂族饱和烃基氧基,卤素,和卤代脂族饱和烃基;
条件是当n=1时,Z是1-四唑基或5-嘧啶基。
本申请另一种实施方式可包括用于防治或预防真菌侵袭的杀真菌组合物,所述组合物包含如上所述的化合物和植物学可接受的载体物质。
本申请另一种实施方式可包括用于防治或预防真菌侵袭植物的方法,所述方法包括以下步骤,将杀真菌有效量的如上所述的一种或多种化合物施用至真菌、植物、和与所述植物邻近的区域中的至少一个中。
本领域技术人员应该理解的是,以下术语可以包括它们定义内的一般性"R"-基团,例如,"术语脂族饱和烃基氧基是指-OR取代基"。也应该理解的是,在以下术语的定义内,针对说明的目的而包括这些"R"基团,但不应理解为其限制关于式I的取代或受式I的取代的限制。
术语“脂族饱和烃基”(alkyl)是指支化的、非支化的、或饱和环状的碳链,包括但不限于甲基,乙基,丙基,丁基,异丙基,异丁基,叔丁基,戊基,己基,环丙基,环丁基,环戊基,环己基等。
术语“烯基”是指包含一个或多个双键的支化的、非支化的、或环状的碳链,包括但不限于乙烯基,丙烯基,丁烯基,异丙烯基,异丁烯基,环丁烯基,环戊烯基,环己烯基等。
术语“炔基”是指包含一个或多个三键的支化或非支化的碳链,包括但不限于丙炔基,丁炔基等。
术语“芳基”或“Ar”指包含0个杂原子的任何芳族环、单环或双环。
术语“杂环”是指包含一个或多个杂原子的任何芳族或非芳族的环、单环或双环。
术语“杂芳基”或“Het”是指包含一个或多个杂原子的任何芳族环、单环或双环。
术语“脂族饱和烃基氧基”是指-OR取代基。
术语“芳氧基”是指-OAr取代基。
术语“杂芳氧基”是指-OHet取代基。
术语“芳基炔基”是指-≡-Ar取代基。
术语“杂芳基炔基”是指-≡-Het取代基。
术语“氰基”是指-C≡N取代基。
术语“羟基”是指-OH取代基。
术语“氨基”是指-NR2取代基。
术语“芳基脂族饱和烃基”是指-脂族饱和烃基-Ar取代基。
术语“杂芳基脂族饱和烃基”是指-脂族饱和烃基-Het取代基。
术语“芳基脂族饱和烃基氧基”是指-O(CH2)nAr,其中n是选自1、2、3、4、5、或6的整数。
术语“杂芳基脂族饱和烃基氧基”是指-O(CH2)nHet,其中n是选自1、2、3、4、5、或6的整数。
术语“卤代脂族饱和烃基氧基”是指-OR取代基,其中R取代有Cl,F,Br,或I,或一个或多个卤素原子的任何组合。
术语“卤代脂族饱和烃基”是指取代有一个或多个卤素原子的脂族饱和烃基。
术语“氰基脂族饱和烃基”取代有氰基的脂族饱和烃基。
术语“卤素”或“卤代”是指一个或多个卤素原子,限定为F,Cl,Br,和I。
术语“硝基”是指-NO2取代基。
术语硫代脂族饱和烃基是指-SR取代基。
在本申请全文中,当提到式I化合物时还包括非对映异构体、对映异构体、及其混合物。在另一种实施方式中,提到的式I也包括其盐或水合物。示例性的盐包括但不限于:氢氯酸盐、氢溴酸盐、和氢碘酸盐。
本领域技术人员还应当理解的是,除非另有说明,允许额外的取代,只要满足化学键合和应变能规则并且产物仍表现杀真菌活性。
本申请另一实施方式为式I化合物的用途,用于保护植物免受致植物病微生物侵袭或用于处理被致植物病微生物侵害的植物,所述用途包括将式I化合物或含有所述化合物的组合物施用至土壤、植物、植物的一部分、叶子、种子、和/或根。
此外,本申请的另一种实施方式为用于保护植物免受致植物病微生物侵袭和/或处理被致植物病微生物侵害的植物的组合物,所述组合物包含式I化合物和植物学可接受的载体物质。
具体实施方式
可通过各种已知技术中的任一种将本申请化合物作为化合物或作为含有所述化合物的制剂来施用。例如,可将所述化合物施用至植物的种子、根或叶子以防治各种真菌,而不破坏植物的商业价值。所述物质可按通常使用的任意制剂类型的形式施用,例如作为溶液剂、粉剂、可润湿粉末、可流动浓缩物、或乳油(emulsifiable concentrate)。
优选地,本申请化合物以制剂形式施用,所述制剂包含一种或多种式I化合物和植物学可接受的载体。可将浓缩制剂分散在水中或其它液体中用于施用,或制剂可以是粉尘或颗粒,其不经进一步处理随即可施用。可根据农业化学领域常见的方法制备所述制剂。
本申请预期使用所有媒介物,可通过所述媒介物配制所述一种或多种化合物用于递送并用作杀真菌剂。通常,作为含水悬浮液或乳液的形式施用制剂。所述悬浮液或乳液可由水可溶、水可悬浮或可乳化制剂制备,当所述水可溶、水可悬浮或可乳化制剂为固体时通常称作可润湿粉末;或者当所述水可溶、水可悬浮或可乳化制剂为液体时通常称作乳油、含水悬浮液或悬浮浓缩物。容易理解的是,可使用能将这些化合物加入其中的任意物质,条件是得到所需的用途而不明显妨碍这些化合物作为抗真菌剂的活性。
可被压制成水可分散颗粒的可润湿粉末包含一种或多种式I化合物、惰性载体和表面活性剂的匀质混合物(intimate mixture)。以可润湿粉末的总重量计,所述可润湿粉末中的化合物的浓度可从约10wt%至约90wt%,更优选从约25wt%至约75wt%。在可润湿粉末制剂的制备中,所述化合物可与任意微细粉碎的固体混合,所述微细粉碎的固体为例如叶蜡石(prophyllite)、滑石、白垩、石膏、漂白土(Fuller's earth)、膨润土、凹凸棒石、淀粉、酪蛋白(casein)、麸质(gluten)、蒙脱土(montmorillonite clay)、硅藻土(diatomaceous earth)、精制硅酸盐(purified silicate)等。在所述操作中,通常将微细粉碎的载体和表面活性剂与所述化合物共混并研磨。
以所述乳油的总重量计,式I化合物的乳油可以包含于合适液体中的常规浓度的所述化合物,例如从约1wt%至约50wt%。可将所述化合物溶解在惰性载体中,所述惰性载体是水混溶性溶剂或水不混溶性有机溶剂和乳化剂的混合物。所述乳油可用水和油稀释以形成水包油乳液形式的喷雾混合物。有用的有机溶剂包括石油的芳族部分特别是高沸点环烷部分和烯部分例如重芳香族石脑油。也可使用其它有机溶剂例如萜烯溶剂包括松香衍生物、脂肪族酮例如环己酮和复杂的醇(complex alchol)例如2-乙氧基乙醇。
可被本申请有利地采用的乳化剂可容易地由本领域技术人员确定并包括各种非离子乳化剂、阴离子乳化剂、阳离子乳化剂和两性乳化剂,或两种或多种乳化剂的共混物。用在制备所述乳油中的非离子乳化剂的实例包括聚亚烷基二醇醚,和脂族饱和烃基和芳基酚、脂肪族醇、脂肪族胺或脂肪酸与环氧乙烷、环氧丙烷的缩合产物,例如乙氧基化脂族饱和烃基酚和用多元醇或聚氧化烯溶解的羧酸酯。阳离子乳化剂包括季铵化合物和脂肪胺盐。阴离子乳化剂包括脂族饱和烃基芳基磺酸的油溶盐(例如,钙盐)、油溶盐或硫酸化聚二醇醚和磷酸化聚二醇醚的合适盐。
本申请化合物的乳油的制备中可采用的代表性有机液体为芳族液体例如二甲苯和丙基苯馏分;或混合的萘馏分、矿物油、取代的芳族有机液体例如邻苯二甲酸二辛酯;煤油(kerosene);各种脂肪酸的二脂族饱和烃基酰胺,特别是脂肪二醇的二甲基酰胺和二醇衍生物例如二甘醇的正丁基醚、乙基醚或甲基醚,三甘醇的甲基醚,石油馏分或烃例如矿物油,芳族溶剂,石蜡油等;植物油,例如大豆油,油菜籽油,橄榄油,蓖麻油,向日葵种子油,椰子油,玉米油,棉籽油,亚麻子油,棕榈油,花生油,红花油,芝麻油,桐油等;以上植物油的酯;和类似物。在乳油的制备中也可采用两种或多种有机液体的混合物。有机液体包括二甲苯和丙基苯馏分,在一些情况下二甲苯是最优选的。在液体制剂中通常采用表面活性分散剂,并且以所述分散剂和一种或多种化合物的组合重量计,所述表面活性分散剂的量为0.1至20wt%。所述制剂也可含有其它相容的添加剂,例如植物生长调节剂和其它农业中使用的生物活性化合物。
含水悬浮液包括一种或多种水不可溶式I化合物分散在含水媒介物中的悬浮液,以含水悬浮液的总重量计,浓度为约1wt%-约50wt%。如下制备悬浮液:精细研磨一种或多种所述化合物,将经研磨的化合物剧烈混合到媒介物中,所述媒介物由水和选自上述相同类型的表面活性剂构成。也可加入其它成分,例如无机盐以及合成胶或天然胶,以增加含水媒介物的密度和粘度。
式I化合物也可作为颗粒制剂的形式施用,所述颗粒制剂可特别用于施用至土壤。以颗粒制剂的总重量计,所述颗粒制剂通常含有分散在惰性载体中的约0.5wt%-约10wt%所述化合物,所述惰性载体完全或大部分由粗糙粉碎的惰性物质组成,所述惰性物质为例如凹凸棒石、膨润土、硅藻土、粘土或相似的廉价物质。所述制剂通常如下制备:将所述化合物溶解在合适的溶剂中,将其施用至颗粒载体,所述颗粒载体已经被预先制成合适的粒度(范围为约0.5至3mm)。合适的溶剂为所述化合物可基本或完全溶于其中的溶剂。所述制剂也可如下制备:将所述载体和化合物和溶剂制成糊状或膏状,然后压碎并干燥得到所需颗粒粒度。
含有式I化合物的粉剂(dust)可以如下制备:匀质混合粉末状的一种或多种所述化合物和合适的粉尘状农用载体(例如高岭粘土、研碎的火山石等)。以粉剂的总重量计,所述粉剂可合适地含有约1%-约10%所述化合物。
所述制剂可额外含有辅助表面活性剂以增强所述化合物沉积、润湿和渗透到目标作物和微生物上。这些辅助表面活性剂可任选作为制剂的组分或作为罐混合物使用。以水的喷雾体积计,所述辅助表面活性剂的量通常从0.01至1.0体积%,优选0.05至0.5体积%。合适的辅助表面活性剂包括但不限于乙氧基化壬基酚、乙氧基化合成醇或乙氧基化天然醇、磺基琥珀酸酯或磺基琥珀酸盐、乙氧基化有机硅、乙氧基化脂肪胺,表面活性剂与矿物油或植物油的共混物,作物油浓缩物(矿物油(85%)+乳化剂(15%));壬基酚乙氧基化物;苄基椰油脂族饱和烃基二甲基季铵盐;石油烃、脂族饱和烃基酯、有机酸、和阴离子表面活性剂的共混物;C9-C11脂族饱和烃基聚糖苷;磷酸化的醇乙氧基化物;天然伯醇(C12-C16)乙氧基化物;二-仲-丁基苯酚EO-PO嵌段共聚物;聚硅氧烷-甲基封端物;壬基酚乙氧基化物+脲硝酸铵;乳化的甲基化的种子油;十三脂族饱和烃基醇(合成)乙氧基化物(8EO);牛油胺乙氧基化物(15EO)和PEG(400)二油酸酯-99。所述制剂也可包括水包油乳液例如在美国专利申请11/495,228中披露的那些,将美国专利申请11/495,228披露的内容并入本文作为参考。
所述制剂可任选包括含有其它杀生物化合物的组合。所述额外的杀生物化合物可以是杀真菌剂、杀昆虫剂、除草剂、杀线虫剂、杀螨剂、杀节肢动物剂(arthropodicide)、杀细菌剂或它们的组合,所述额外的杀生物化合物在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物的活性。因此,在所述实施方式中,将所述其它杀生物化合物作为增补毒剂使用,用于相同或不同的杀生物用途。所述组合中的所述式I化合物和杀生物化合物通常可以1:100至100:1的重量比存在。
本申请化合物也可与其它杀真菌剂组合形成杀真菌混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种其它杀真菌剂联合施用,从而防治更宽范围的不期望病害。当与其它杀真菌剂联合施用时,本申请要求保护的化合物可与一种或多种其它杀真菌剂配制在一起,可与一种或多种其它杀真菌剂桶混(tank mix)在一起,或可与一种或多种其它杀真菌剂顺序施用。所述其它杀真菌剂可包括2-(氰硫基甲硫基)-苯并噻唑(2-(thiocyanatomethylthio)-benzothiazole),2-苯基-苯酚(2-phenylphenol),8-羟基喹啉硫酸盐(8-hydroxyquinoline sulfate),辛唑嘧菌胺(ametoctradin),吲唑磺菌胺(amisulbrom),抗霉素(antimycin),白粉寄生孢(Ampelomyces quisqualis),阿扎康唑(azaconazole),腈嘧菌酯(azoxystrobin),芽孢杆菌(Bacillus subtilis),芽孢杆菌菌株QST713(Bacillus subtilis strain QST713),苯霜灵(benalaxyl),苯菌灵(benomyl),苯噻菌胺酯(benthiavalicarb-isopropyl),苯并烯氟菌唑(benzovindiflupyr),苄基氨基苯-磺酸(BABS)盐(benzylaminobenzene-sulfonate(BABS)salt),碳酸氢盐(bicarbonates),联苯类化合物(biphenyl),叶枯唑(bismerthiazol),联苯三唑醇(bitertanol),联苯吡菌胺(bixafen),灭瘟素(blasticidin-S),硼砂(borax),波尔多液(Burgundy mixture),烟酰胺(boscalid),糠菌唑(bromuconazole),乙嘧酚磺酸酯(bupirimate),石硫合剂(calcium polysulfide),敌菌丹(captafol),克菌丹(captan),多菌灵(carbendazim),萎锈灵(carboxin),环丙酰菌胺(carpropamid),香芹酮(carvone),氯芬同(chlazafenone),地茂散(chloroneb),百菌清(chlorothalonil)、乙菌利(chlozolinate),盾壳霉(Coniothyrium Minitans),氢氧化铜(copper hydroxide),辛酸酮(copper octanoate),王铜(copper oxychloride),硫酸铜(copper sulfate),碱式硫酸铜(copper sulfate(tribasic)),氧化亚铜(cuprous oxide),氰霜唑(cyazofamid),环氟苄酰胺(cyflufenamid),霜脲氰(cymoxanil),环菌唑(cyproconazole),嘧菌环胺(cyprodinil),棉隆(dazomet),咪菌威(debacarb),亚乙基二-(二硫代氨基甲酸)二铵(diammonium ethylenebis-(dithiocarbamate)),苯氟磺胺(dichlofluanid),双氯酚(dichlorophen),双氯氰菌胺(diclocymet),哒菌酮(diclomezine),氯硝胺(dichloran),乙霉威(diethofencarb),苯醚甲环唑(difenoconazole),野燕枯离子(difenzoquat ion),氟嘧菌胺(diflumetorim),烯酰吗啉(dimethomorph),醚菌胺(dimoxystrobin),烯唑醇(diniconazole),精烯唑醇(diniconazole-M),消螨通(dinobuton),二硝巴豆酸酯(dinocap),二苯基胺(diphenylamine),二氰蒽醌(dithianon),十二环吗啉(dodemorph),十二环吗啉乙酸盐(dodemorph acetate),多果定(dodine),多果定游离碱(dodine freebase),敌瘟磷(edifenphos),enestrobin,烯肟菌酯(enestroburin),氟环唑(epoxiconazole),噻唑菌胺(ethaboxam),乙氧喹啉(ethoxyquin),土菌灵(etridiazole),噁唑菌酮(famoxadone),咪唑菌酮(fenamidone),氯苯嘧啶醇(fenarimol),腈苯唑(fenbuconazole),甲呋酰胺(fenfuram),环酰菌胺(fenhexamid),稻瘟酰胺(fenoxanil),拌种咯(fenpiclonil),苯锈啶(fenpropidin),丁苯吗啉(fenpropimorph),fenpyrazamine,三苯锡(fentin),三苯基乙酸锡(fentin acetate),三苯基氢氧化锡(fentin hydroxide),福美铁(ferbam),嘧菌腙(ferimzone),氟啶胺(fluazinam),咯菌腈(fludioxonil),氟吗啉(flumorph),氟吡菌胺(fluopicolide),氟吡菌酰胺(fluopyram),氟氯菌核利(fluoroimide),氟嘧菌酯(fluoxastrobin),氟喹唑(fluquinconazole),氟硅唑(flusilazole),磺菌胺(flusulfamide),氟噻菌净(flutianil),氟酰胺(flutolanil),粉唑醇(flutriafol),氟唑菌酰胺(fluxapyroxad),灭菌丹(folpet),甲醛(formaldehyde),三乙膦酸(fosetyl),三乙膦酸铝(fosetyl-aluminium),麦穗宁(fuberidazole),呋霜灵(furalaxyl),呋吡菌胺(furametpyr),双胍辛(guazatine),双胍辛乙酸盐(guazatine acetates),四硫钠(GY-81),六氯苯(hexachlorobenzene),己唑醇(hexaconazole),噁霉灵(hymexazol),抑霉唑(imazalil),硫酸抑霉唑(imazalilsulfate),亚胺唑(imibenconazole),双胍辛胺(iminoctadine),三乙酸双胍辛胺(iminoctadine triacetate),双胍辛胺三(对十二脂族饱和烃基苯磺酸盐)[iminoctadinetris(albesilate)],iodocarb,种菌唑(ipconazole),ipfenpyrazolone,异稻瘟净(iprobenfos),异菌脲(iprodione),缬霉威(iprovalicarb),稻瘟灵(isoprothiolane),吡唑萘菌胺(isopyrazam),异噻菌胺(isotianil),春雷霉素(kasugamycin),春雷霉素盐酸盐水合物(kasugamycin hydrochloride hydrate),醚菌甲酯(kresoxim-methyl),laminarin,代森锰铜(mancopper),代森锰锌(mancozeb),双炔酰菌胺(mandipropamid),代森锰(maneb),精甲霜灵(mefenoxam),嘧菌胺(mepanipyrim),灭锈胺(mepronil),二硝巴豆酸酯(meptyl-dinocap),氯化汞(mercuric chloride),氧化汞(mercuric oxide),氯化亚汞(mercurous chloride),甲霜灵(metalaxyl),精甲霜灵(metalaxyl-M),威百亩(metam),安百亩(metam-ammonium),metam-potassium,威百亩(metam-sodium),叶菌唑(metconazole),磺菌威(methasulfocarb),碘甲烷(methyl iodide),异硫氰酸甲酯(methyl isothiocyanate),代森联(metiram),苯氧菌胺(metominostrobin),苯菌酮(metrafenone),米多霉素(mildiomycin),腈菌唑(myclobutanil),代森钠(nabam),酞菌异丙酯(nitrothal-isopropyl),氟苯嘧啶醇(nuarimol),辛噻酮(octhilinone),呋酰胺(ofurace),油酸(脂肪酸)(oleic acid(fatty acid)),肟醚菌胺(orysastrobin),噁霜灵(oxadixyl),喹啉铜(oxine-copper),富马酸噁咪唑(oxpoconazole fumarate),氧化萎锈灵(oxycarboxin),稻瘟酯(pefurazoate),戊菌唑(penconazole),戊菌隆(pencycuron),戊苯吡菌胺(penflufen),五氯酚(pentachlorophenol),月桂酸五氯苯酯(pentachlorophenyl laurate),吡噻菌胺(penthiopyrad),乙酸苯汞(phenylmercuryacetate),膦酸(phosphonic acid),四氯苯酞(phthalide),啶氧菌酯(picoxystrobin),多抗霉素B(polyoxin B),多抗霉素(polyoxins),多氧霉素(polyoxorim),碳酸氢钾(potassium bicarbonate),羟基喹啉硫酸钾(potassium hydroquinoline sulfate),烯丙苯噻唑(probenazole),咪鲜胺(prochloraz),腐霉利(procymidone),霜霉威(propamocarb),盐酸霜霉威(propamocarb hydrochloride),丙环唑(propiconazole),丙森锌(propineb),丙氧喹啉(proquinazid),丙硫菌唑(prothioconazole),吡唑醚菌酯(pyraclostrobin),唑胺菌酯(pyrametostrobin),唑菌酯(pyraoxystrobin),吡菌磷(pyrazophos),pyribencarb,稗草丹(pyributicarb),啶斑肟(pyrifenox),嘧霉胺(pyrimethanil),pyriofenone,咯喹酮(pyroquilon),灭藻醌(quinoclamine),苯氧喹啉(quinoxyfen),五氯硝基苯(quintozene),大虎杖提取物(Reynoutria sachalinensisextract),环丙吡菌胺(sedaxane),硅噻菌胺(silthiofam),硅氟唑(simeconazole),2-苯基苯酚钠(sodium 2-phenyl phenoxide),碳酸氢钠(sodium bicarbonate),五氯苯酚钠(sodium pentachlorophenoxide),螺环菌胺(spiroxamine),硫黄(sulfur),SYP-Z048,木焦油(tar oil),戊唑醇(tebuconazole),异丁乙氧喹啉(tebufloquin),四氯硝基苯(tecnazene),四氟醚唑(tetraconazole),噻菌灵(thiabendazole),噻氟菌胺(thifluzamide),甲基硫菌灵(thiophanate-methyl),福美双(thiram),噻酰菌胺(tiadinil),甲基立枯磷(tolclofos-methyl),甲苯氟磺胺(tolylfluanid),三唑酮(triadimefon),三唑醇(triadimenol),咪唑嗪(triazoxide),三环唑(tricyclazole),十三吗啉(tridemorph),肟菌酯(trifloxystrobin),氟菌唑(triflumizole),嗪氨灵(triforine),灭菌唑(triticonazole),井冈霉素(validamycin),valifenalate,valiphenal,乙烯菌核利(vinclozolin),代森锌(zineb),福美锌(ziram),苯酰菌胺(zoxamide),假丝酵母(Candida oleophila),枯萎病菌(Fusarium oxysporum),绿粘帚霉属种(Gliocladium spp.),大隔孢拟射脉霉素(Phlebiopsis gigantea),灰绿链霉菌(Streptomyces griseoviridis),木霉属种(Trichoderma spp.),(RS)-N-(3,5-二氯苯基)-2-(甲氧基甲基)-琥珀酰亚胺((RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide),1,2-二氯丙烷(1,2-dichloropropane),1,3-二氯-1,1,3,3-四氟丙酮水合物(1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate),1-氯-2,4-二硝基萘(1-chloro-2,4-dinitronaphthalene),1-氯-2-硝基丙烷(1-chloro-2-nitropropane),2-(2-十七脂族饱和烃基-2-咪唑啉-1-基)乙醇(2-(2-heptadecyl-2-imidazolin-1-yl)ethanol),2,3-二氢-5-苯基-1,4-二硫杂环己二烯-1,1,4,4-四氧化物(2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide),乙酸2-甲氧基乙基汞(2-methoxyethylmercury acetate),氯化2-甲氧基乙基汞(2-methoxyethylmercurychloride),硅酸2-甲氧基乙基汞(2-methoxyethylmercury silicate),3-(4-氯苯基)-5-甲基绕丹宁(3-(4-chlorophenyl)-5-methyl rhodanine),硫氰酸4-(2-硝基丙-l-烯基)苯酯(4-(2-nitroprop-l-enyl)phenyl thiocyanateme),氨丙膦酸(ampropylfos),敌菌灵(anilazine),氧化福美双(azithiram),多硫化钡(barium polysulfide),铁菌清(Bayer32394),麦锈灵(benodanil),醌肟腙(benquinox),丙唑草隆(bentaluron),苄烯酸(benzamacril);苄烯酸异丁酯(benzamacril-isobutyl),苯杂吗(benzamorf),乐杀螨(binapacryl),硫酸二(甲基汞)(bis(methylmercury)sulfate),氧化二(三丁基锡)(bis(tributyltin)oxide),丁硫啶(buthiobate),草菌盐(cadmium calcium copper zincchromate sulfate),吗菌威(carbamorph),氰粉灵(CECA),灭瘟唑(chlobenthiazone),双胺灵(chloraniformethan),苯咪唑菌(chlorfenazole),四氯喹噁啉(chlorquinox),咪菌酮(climbazole),二(3-苯基水杨酸)铜(copper bis(3-phenylsalicylate)),铬酸铜锌(copper zinc chromate),硫杂灵(cufraneb),硫酸肼铜(cupric hydrazinium sulfate),福美铜氯(cuprobam),环糠酰胺(cyclafuramid),氰菌灵(cypendazole),酯菌胺(cyprofuram),癸磷锡(decafentin),二氯萘醌(dichlone),菌核利(dichlozoline),苄氯三唑醇(diclobutrazol),甲菌定(dimethirimol),敌螨通(dinocton),硝辛酯(dinosulfon),硝丁酯(dinoterbon),吡菌硫(dipyrithione),灭菌磷(ditalimfos),多敌菌(dodicin),敌菌酮(drazoxolon),稻瘟净(EBP),枯瘟净(ESBP),乙环唑(etaconazole),代森硫(etem),乙嘧酚(ethirim),敌磺钠(fenaminosulf),咪菌腈(fenapanil),种衣酯(fenitropan),三氟苯唑(fluotrimazole),灭菌胺(furcarbanil),呋菌唑(furconazole),顺式呋菌唑(furconazole-cis),拌种胺(furmecyclox),呋菌隆(furophanate),果绿啶(glyodine),灰黄霉素(griseofulvin),丙烯酸喹啉酯(halacrinate),噻茂铜(Hercules3944),环己硫磷(hexylthiofos),丙环啶菌(ICIA0858),壬氧磷胺(isopamphos),氯苯咪菌酮(isovaledione),邻酰胺(mebenil),咪卡病西(mecarbinzid),肼叉噁唑酮(metazoxolon),呋菌胺(methfuroxam),氰胍甲汞(methylmercury dicyandiamide),噻菌胺(metsulfovax),代森环(milneb),粘氯酸酐(mucochloric anhydride),甲菌利(myclozolin),N-3,5-二氯苯基琥珀酰亚胺(N-3,5-dichlorophenylsuccinimide),N-3-硝基苯基衣康酰亚胺(N-3-nitrophenylitaconimide),多马霉素(natamycin),N-乙基汞基-4-甲苯磺酰苯胺(N-ethylmercurio-4-toluenesulfonanilide),二(二甲基二硫代氨基甲酸)镍(nickel bis(dimethyldithiocarbamate)),八氯酮(OCH),二甲基二硫代氨基甲酸苯汞(phenylmercury dimethyldithiocarbamate),硝酸苯汞(phenylmercury nitrate),氯瘟磷(phosdiphen),硫菌威(prothiocarb);盐酸硫菌威(prothiocarb hydrochloride),吡喃灵(pyracarbolid),啶菌腈(pyridinitril),吡氧氯(pyroxychlor),氯吡呋醚(pyroxyfur),5-乙酰基-8-羟基喹啉(quinacetol);5-乙酰基-8-羟基喹啉硫酸盐(quinacetol sulfate),酯菌腙(quinazamid),喹唑菌酮(quinconazole),吡咪唑菌(rabenzazole),水杨酰胺(salicylanilide),唑菌庚醇(SSF-109,戊苯砜(sultropen),福代硫(tecoram),噻二氟(thiadifluor),噻菌腈(thicyofen),苯菌胺(thiochlorfenphim),硫菌灵(thiophanate),克杀螨(thioquinox),硫氰苯甲酰胺(tioxymid),三唑磷胺(triamiphos),嘧菌醇(triarimol),叶锈特(triazbutil),水杨菌胺(trichlamide),福美甲胂(urbacid),灭杀威(zarilamid),及其任何组合。
此外,本申请所述的化合物可与其它杀虫剂结合,包括杀昆虫剂、杀线虫剂、杀螨剂、杀节肢动物剂(arthropodicide)、杀细菌剂或它们的组合,所述其它杀害虫剂在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物的活性以形成杀虫混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种其它杀虫剂联合施用,从而防治更宽范围的不期望害虫。当与其它杀虫剂联合施用时,本申请要求保护的化合物可与一种或多种其它杀虫剂配制在一起、可与一种或多种其它杀虫剂桶混(tank mix)在一起或可与一种或多种其它杀虫剂顺序施用。常见的杀昆虫剂包括但不限于:1,2-二氯丙烷(1,2-dichloropropane)、阿维菌素(abamectin)、高灭磷(acephate)、吡虫清(acetamiprid)、家蝇磷(acethion)、乙酰虫腈(acetoprole)、氟酯菊酯(acrinathrin)、丙烯腈(acrylonitrile)、棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、艾氏剂(aldrin)、丙烯除虫菊(allethrin)、阿洛氨菌素(allosamidin)、除害威(allyxycarb)、α-氯氰菊酯(alpha-cypermethrin)、α-蜕皮素(alpha-ecdysone)、α-硫丹(alpha-endosulfan)、赛果(amidithion)、灭害威(aminocarb)、胺吸磷(amiton)、草酸胺吸磷(amiton oxalate)、虫螨脒(amitraz)、新烟碱(anabasine)、艾噻达松(athidathion)、艾扎丁(azadirachtin)、唑啶磷(azamethiphos)、益棉磷(azinphos-ethyl)、保棉磷(azinphos-methyl)、偶氮磷(azothoate)、六氟硅酸钡(barium hexafluorosilicate)、熏虫菊(barthrin)、唑虫威(bendiocarb)、丙硫克拜威(benfuracarb)、杀虫磺(bensultap)、β-氟氯氰菊酯(beta-cyfluthrin)、β-氯氰菊酯(beta-cypermethrin)、联苯菊酯(bifenthrin)、反式丙烯除虫菊(bioallethrin)、bioethanomethrin、生物氯菊酯(biopermethrin)、双二氟虫脲(bistrifluron)、硼砂(borax)、硼酸(boric acid)、溴苯烯磷(bromfenvinfos)、溴烯杀(bromocyclen)、溴-DDT、溴硫磷(bromophos)、乙基溴硫磷(bromophos-ethyl)、合杀威(bufencarb)、噻嗪酮(buprofezin)、畜虫威(butacarb)、特嘧硫磷(butathiofos)、丁叉威(butocarboxim)、丁酯磷(butonate)、氧丁叉威(butoxycarboxim)、硫线磷(cadusafos)、砷酸钙(calcium arsenate)、石硫合剂(calcium polysulfide)、毒杀芬(camphechlor)、氯灭杀威(carbanolate)、甲萘威(carbaryl)、虫螨威(carbofuran)、二硫化碳(carbondisulfide)、四氯化碳(carbon tetrachloride)、三硫磷(carbophenothion)、丁硫克百威(carbosulfan)、巴丹(cartap)、盐酸巴丹(cartap hydrochloride)、氯虫酰胺(chlorantraniliprole)、冰片丹(chlorbicyclen)、氯丹(chlordane)、开蓬(chlordecone)、氯苯脒(chlordimeform)、盐酸氯苯脒(chlordimeform hydrochloride)、壤土氯磷(chlorethoxyfos)、氟唑虫清(chlorfenapyr)、毒虫畏(chlorfenvinphos)、定虫隆(chlorfluazuron)、氯甲磷(chlormephos)、氯仿(chloroform)、氯化苦(chloropicrin)、氯腈肟磷(chlorphoxim)、氯吡唑磷(chlorprazophos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、氯甲硫磷(chlorthiophos)、环虫酰胺(chromafenozide)、瓜菊酯I(cinerin I)、瓜菊酯I(cinerin II)、瓜菊酯(cinerins)、左旋反灭虫菊酯(cismethrin)、除线威(cloethocarb)、氯氰碘柳胺(closantel)、噻虫胺(clothianidin)、乙酰亚砷酸铜(copper acetoarsenite)、砷酸铜(copper arsenate)、环烷酸铜(coppernaphthenate)、油酸铜(copper oleate)、库马磷(coumaphos)、畜虫磷(coumithoate)、克罗米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、氟铝酸钠(cryolite)、苯腈磷(cyanofenphos)、杀螟磷(cyanophos)、果虫磷(cyanthoate)、氰虫酰胺(cyantraniliprole)、环戊烯菊酯(cyclethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、氯氰菊酯(cypermethrin)、苯醚氰菊酯(cyphenothrin)、灭蝇胺(cyromazine)、赛灭磷(cythioate)、DDT、一甲呋喃丹(decarbofuran)、溴氰菊酯(deltamethrin)、田乐磷(demephion)、田乐磷-O(demephion-O)、田乐磷-S(demephion-S)、内吸磷(demeton)、甲基内吸磷(demeton-methyl)、内吸磷-O(demeton-O)、内吸磷-O-甲基(demeton-O-methyl)、内吸磷-S(demeton-S)、内吸磷-S-甲基(demeton-S-methyl)、内吸磷-S-甲基硫(demeton-S-methylsulphon)、杀螨硫隆(diafenthiuron)、氯亚磷(dialifos)、硅藻土(diatomaceous earth)、二嗪农(diazinon)、异氯硫磷(dicapthon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)、N-(3-甲基苯基)氨基甲酸甲酯(dicresyl)、百治磷(dicrotophos)、环虫腈(dicyclanil)、狄氏剂(dieldrin)、氟脲杀(diflubenzuron)、丙羟茶碱(dilor)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、地麦威(dimetan)、乐果(dimethoate)、苄菊酯(dimethrin)、甲基毒虫畏(dimethylvinphos)、敌蝇威(dimetilan)、消螨酚(dinex)、dinex-diclexine、丙硝酚(dinoprop)、戊硝酚(dinosam)、呋虫胺(dinotefuran)、噁茂醚(diofenolan)、杀抗松(dioxabenzofos)、二氧威(dioxacarb)、敌噁磷(dioxathion)、乙拌磷(disulfoton)、噻喃磷(dithicrofos)、右旋柠檬烯(d-limonene)、二硝甲酚(DNOC)、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、多拉克汀(doramectin)、促蜕皮甾酮(ecdysterone)、甲氨基阿维菌素(emamectin)、苯甲酸甲氨基阿维菌素(emamectin benzoate)、多杀威(EMPC)、烯炔菊酯(empenthrin)、硫丹(endosulfan)、因毒磷(endothion)、异狄氏剂(endrin)、苯硫磷(EPN)、保幼醚(epofenonane)、爱普瑞菌素(eprinomectin)、Es-生物烯丙菊酯(esdepalléthrine)、高氰戊菊酯(esfenvalerate)、etaphos、苯虫威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、益果(ethoate-methyl)、灭克磷(ethoprophos)、甲酸乙酯(ethyl formate)、乙基-DDD、1,2-二溴乙烷(ethylene dibromide)、1,2-二氯乙烷(ethylene dichloride)、环氧乙烷(ethylene oxide)、醚菊酯(etofenprox)、乙嘧硫磷(etrimfos)、EXD、氨磺磷(famphur)、克线磷(fenamiphos)、抗螨唑(fenazaflor)、皮蝇磷(fenchlorphos)、乙苯威(fenethacarb)、五氟苯菊酯(fenfluthrin)、杀螟硫磷(fenitrothion)、丁苯威(fenobucarb)、fenoxacrim、双氧威(fenoxycarb)、吡氯氰菊酯(fenpirithrin)、甲氰菊酯(fenpropathrin)、丰索磷(fensulfothion)、倍硫磷(fenthion)、倍硫磷-乙基(fenthion-ethyl)、氰戊菊酯(fenvalerate)、锐劲特(fipronil)、氟啶虫酰胺(flonicamid)、氟虫酰胺(flubendiamide)、氟氯双苯隆(flucofuron)、氟螨脲(flucycloxuron)、氟氰菊酯(flucythrinate)、嘧虫胺(flufenerim)、氟虫脲(flufenoxuron)、氟丙苄醚(flufenprox)、氟胺氰菊酯(fluvalinate)、地虫磷(fonofos)、伐虫脒(formetanate)、盐酸伐虫脒(formetanatehydrochloride)、安果(formothion)、胺甲威(formparanate)、盐酸胺甲威(formparanatehydrochloride)、丁苯硫磷(fosmethilan)、甲基毒死蜱(fospirate)、伐线丹(fosthietan)、呋线威(furathiocarb)、糠醛菊酯(furethrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、γ-HCH、卤醚菊酯(halfenprox)、特丁苯酰肼(halofenozide)、HCH、HEOD、七氯(heptachlor)、庚虫磷(heptenophos)、速杀硫磷(heterophos)、氟铃脲(hexaflumuron)、艾氏剂(HHDN)、灭蚁腙(hydramethylnon)、氰化氢(hydrogen cyanide)、蒙五一二(hydroprene)、喹啉威(hyquincarb)、吡虫啉(imidacloprid)、咪炔菊酯(imiprothrin)、茚虫威(indoxacarb)、碘甲烷(iodomethane)、丰丙磷(IPSP)、氯唑磷(isazofos)、碳氯灵(isobenzan)、水胺硫磷(isocarbophos)、异艾氏剂(isodrin)、丙胺磷(isofenphos)、丙胺磷-甲基(isofenphos-methyl)、异丙威(isoprocarb)、稻瘟灵(isoprothiolane)、叶蚜磷(isothioate)、噁唑磷(isoxathion)、齐墩螨素(ivermectin)、茉莉菊酯I(jasmolin I)、茉莉菊酯II(jasmolin II)、碘硫磷(jodfenphos)、保幼激素I(juvenile hormone I)、保幼激素II(juvenile hormone II)、保幼激素III(juvenile hormone III)、克来范(kelevan)、蒙七七七(kinoprene)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、砷酸铅(lead arsenate)、lepimectin、溴苯磷(leptophos)、林丹(lindane)、啶虫磷(lirimfos)、氟丙氧脲(lufenuron)、噻唑磷(lythidathion)、马拉硫磷(malathion)、苄丙二腈(malonoben)、叠氮磷(mazidox)、灭蚜磷(mecarbam)、甲基灭蚜磷(mecarphon)、灭蚜松(menazon)、二噻磷(mephosfolan)、氯化亚汞(mercurous chloride)、甲亚砜磷(mesulfenfos)、氰氟虫腙(metaflumizone)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、灭虫威(methiocarb)、丁烯胺磷(methocrotophos)、灭多虫(methomyl)、蒙五一五(methoprene)、甲氧滴滴涕(emthoxychlor)、甲氧苯酰肼(methoxyfenozide)、溴甲烷(methyl bromide)、异硫氰酸甲酯(methyl isothiocyanate)、甲基氯仿(methylchloroform)、二氯甲烷(methylene chloride)、氧卞氟菊酯(metofluthrin)、速灭威(metolcarb)、噁虫酮(metoxadiazone)、速灭磷(mevinphos)、自克威(mexacarbate)、米尔螨素(milbemectin)、米尔贝肟(milbemycin oxime)、丙胺氟磷(mipafox)、灭蚁灵(mirex)、molosultap、久效磷(monocrotophos)、杀虫单(monomehypo)、杀虫单(monosultap)、茂果(morphothion)、莫西克丁(moxidectin)、萘肽磷(naftalofos)、二溴磷(naled)、萘(naphthalene)、烟碱(nicotine)、氟蚁灵(nifluridide)、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、腈叉威(nitrilacarb)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氧乐果(omethoate)、甲氨叉威(oxamyl)、砜吸磷(oxydemeton-methyl)、异砜磷(oxydeprofos)、砜拌磷(oxydisulfoton)、对-二氯苯(para-dichlorobenzene)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、氟幼脲(penfluron)、五氯酚(pentachlorophenol)、苄氯菊脂(permethrin)、芬硫磷(phenkapton)、苯醚菊酯(phenothrin)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、棉安磷(phosfolan)、亚胺硫磷(phosmet)、对氯硫磷(phosnichlor)、磷胺(phosphamidon)、磷化氢(phosphine)、肟硫磷(phoxim)、甲基肟硫磷(phoxim-methyl)、甲胺嘧磷(pirimetaphos)、抗蚜威(pirimicarb)、乙基虫螨磷(pirimiphos-ethyl)、甲基虫螨磷(pirimiphos-methyl)、亚砷酸钾(potassium arsenite)、硫氰酸钾(potassium thiocyanate)、pp'-DDT、炔酮菊酯(prallethrin)、早熟素I(precocene I)、早熟素II(precocene II)、早熟素III(precocene III)、酰胺嘧啶啉(primidophos)、丙溴磷(profenofos)、环丙氟灵(profluralin)、蜱虱威(promacyl)、猛杀威(promecarb)、丙虫磷(propaphos)、烯虫磷(propetamphos)、残杀威(propoxur)、乙噻唑磷(prothidathion)、丙硫磷(prothiofos)、发果(prothoate)、protrifenbute、吡唑硫磷(pyraclofos)、嘧啶威(pyrafluprole)、吡菌磷(pyrazophos)、反灭虫菊(pyresmethrin)、除虫菊酯I(pyrethrin I)、除虫菊酯II(pyrethrin II)、除虫菊(pyrethrins)、哒螨酮(pyridaben)、啶虫丙醚(pyridalyl)、打杀磷(pyridaphenthion)、pyrifluquinazon、嘧胺苯醚(pyrimidifen)、嘧啶磷(pyrimitate)、吡啶醇(pyriprole)、蚊蝇醚(pyriproxyfen)、苦木(quassia)、喹噁啉(quinalphos)、甲基喹噁啉(quinalphos-methyl)、喹塞昂(quinothion)、碘醚柳胺(rafoxanide)、苄呋菊酯(resmethrin)、鱼藤酮(rotenone)、鱼泥汀(ryania)、沙巴草(sabadilla)、八甲磷(schradan)、赛拉菌素(selamectin)、灭虫硅醚(silafluofen)、硅胶(silica gel)、亚砷酸钠(sodium arsenite)、氟化钠(sodium fluoride)、六氟硅酸钠(sodiumhexafluorosilicate)、硫氰酸钠(sodium thiocyanate)、苏果(sophamide)、多虫菌素(spinetoram)、艾克敌(spinosad)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、磺苯醚隆(sulcofuron)、磺苯醚隆钠(sulcofuron-sodium)、氟虫胺(sulfluramid)、硫特普(sulfotep)、氟啶虫胺腈(sulfoxaflor)、氟化硫(sulfuryl fluoride)、乙丙硫磷(sulprofos)、τ-氟胺氰菊酯(tau-fluvalinate)、噻螨威(tazimcarb)、滴滴滴(TDE)、双苯酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、嘧丙磷(tebupirimfos)、伏虫隆(teflubenzuron)、七氟菊酯(tefluthrin)、双硫磷(temephos)、特普(TEPP)、环戊烯丙菊酯(terallethrin)、特丁磷(terbufos)、四氯乙烷(tetrachloroethane)、杀虫畏(tetrachlorvinphos)、胺菊酯(tetramethrin)、tetramethylfluthrin、θ-氯氰菊酯(theta-cypermethrin)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、噻氯磷(thicrofos)、抗虫威(thiocarboxime)、硫环杀(thiocyclam)、草酸硫环杀(thiocyclamoxalate)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、甲基乙拌磷(thiometon)、杀虫双(thiosultap)、杀虫双-二钠(thiosultap-disodium)、杀虫双-单钠(thiosultap-monosodium)、敌贝特(thuringiensin)、唑虫酰胺(tolfenpyrad)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、反氯菊酯(transpermethrin)、苯螨噻(triarathene)、醚苯磺隆(triazamate)、三唑磷(triazophos)、敌百虫(trichlorfon)、异皮蝇磷(trichlormetaphos-3)、壤虫磷(trichloronat)、氯苯乙丙磷(trifenofos)、杀虫隆(triflumuron)、混杀威(trimethacarb)、硫烯酸酯(triprene)、蚜灭多(vamidothion)、氟吡唑虫(vaniliprole)、二甲威(XMC)、灭杀威(xylylcarb)、ζ-氯氰菊酯(zeta-cypermethrin)、zolaprofos和它们的任意组合。
此外,本申请所述的化合物可在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物活性的除草剂结合以形成杀虫混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种除草剂联合施用,从而防治更宽范围的不期望植物。当与除草剂联合施用时,本申请要求保护的化合物可与一种或多种除草剂配制在一起、可与一种或多种除草剂桶混(tankmix)在一起或可与一种或多种除草剂顺序施用。常见的除草剂包括但不限于:4-CPA;4-CPB;4-CPP;2,4-D;3,4-DA;2,4-DB;3,4-DB;2,4-DEB;2,4-DEP;3,4-DP;2,3,6-TBA;2,4,5-T;2,4,5-TB;刈草胺(acetochlor)、三氟羧草醚(acifluorfen)、苯草醚(aclonifen)、丙烯醛(acrolein)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、烯丙醇(allyl alcohol)、五氯戊酮酸(alorac)、特津酮(ametridione)、莠灭净(ametryn)、特草嗪酮(amibuzin)、氨唑草酮(amicarbazone)、磺氨磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨基吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、莎稗磷(anilofos)、疏草隆(anisuron)、磺草灵(asulam)、莠去通(atraton)、莠去津(atrazine)、唑啶炔草(azafenidin)、四唑磺隆(azimsulfuron)、叠氮净(aziprotryne)、燕麦灵(barban)、BCPC、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、bencarbazone、氟草胺(benfluralin)、呋草磺(benfuresate)、苄嘧磺隆(bensulfuron)、地散磷(bensulide)、灭草松(bentazone)、胺酸杀(benzadox)、双苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、噻草隆(benzthiazuron)、bicyclopyrone、治草醚(bifenox)、双丙氨酰膦(bilanafos)、双嘧苯甲酸(bispyribac)、硼砂(borax)、除草定(bromacil)、糠草腈(bromobonil)、溴丁酰草胺(bromobutide)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)、杀莠敏(brompyrazon)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草膦(butamifos)、丁烯草胺(butenachlor)、特咪唑草(buthidazole)、丁噻隆(buthiuron)、地乐胺(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、苏达灭(butylate)、二甲胂酸(cacodylic acid)、苯酮唑(cafenstrole)、氯酸钙(calciumchlorate)、氰氨化钙(calcium cyanamide)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、长杀草(carbetamide)、特噁唑威(carboxazole)、草败死(chlorprocarb)、氟酮唑草(carfentrazone)、CDEA、CEPC、氯硝醚(chlomethoxyfen)、草灭平(chloramben)、丁酰草胺(chloranocryl)、炔禾灵(chlorazifop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、乙氧苯隆(chloreturon)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氟嘧杀(chlorflurazole)、氯甲丹(chlorflurenol)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、草枯醚(chlornitrofen)、三氯丙酸(chloropon)、氯麦隆(chlorotoluron)、枯草隆(chloroxuron)、羟敌草腈(chloroxynil)、氯苯胺灵(chlorpropham)、绿磺隆(chlorsulfuron)、氯酞酸(chlorthal)、草克乐(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、咯草隆(cisanilide)、烯草酮(clethodim)、碘氯啶酯(cliodinate)、炔草酯(clodinafop)、氯丁草(clofop)、异噁草酮(clomazone)、稗草胺(clomeprop)、调果酸(cloprop)、环丁烯草酮(cloproxydim)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、CMA、硫酸铜(copper sulfate)、CPMF、CPPC、醚草敏(credazine)、甲酚(cresol)、苄草隆(cumyluron)、氰草净(cyanatryn)、氰草津(cyanazine)、草灭特(cycloate)、环丙磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、牧草快(cyperquat)、环丙津(cyprazine)、三环塞草胺(cyprazole)、环酰草胺(cypromid)、香草隆(daimuron)、茅草枯(dalapon)、棉隆(dazomet)、敌草乐(delachlor)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-allate)、麦草畏(dicamba)、敌草腈(dichlobenil)、氯全隆(dichloralurea)、苄胺灵(dichlormate)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、氯甲草(diclofop)、唑嘧磺胺(diclosulam)、二乙除草双(diethamquat)、安塔(diethatyl)、氟苯戊烯酸(difenopenten)、枯莠隆(difenoxuron)、苯敌快(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、克草胺(dimethachlor)、戊草津(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、敌灭生(dimexano)、敌米达松(dimidazon)、敌乐胺(dinitramine)、地乐特(dinofenate)、丙硝酚(dinoprop)、戊硝酚(dinosam)、地乐酚(dinoseb)、特乐酚(dinoterb)、草乃敌(diphenamid)、杀草净(dipropetryn)、敌草快(diquat)、2,4-滴硫酸(disul)、氟硫草定(dithiopyr)、敌草隆(diuron)、DMPA、DNOC、DSMA、EBEP、甘草津(eglinazine)、草藻灭(endothal)、磺唑草(epronaz)、EPTC、抑草蓬(erbon)、禾草畏(esprocarb)、丁氟消草(ethalfluralin)、胺苯磺隆(ethametsulfuron)、噻二唑隆(ethidimuron)、抑草威(ethiolate)、乙呋草磺(ethofumesate)、氯氟草醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、硝草酚(etinofen)、乙胺草醚(etnipromid)、乙氧苯酰草(etobenzanid)、EXD、酰苯磺威(fenasulam)、2,4,5-涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、fenoxasulfone、氯苯氧乙醇(fenteracol)、噻唑禾草灵(fenthiaprop)、四唑草胺(fentrazamide)、非草隆(fenuron)、硫酸亚铁(ferrous sulfate)、氟燕灵(flamprop)、强氟燕灵(flamprop-M)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr)、氟唑啶草(flumetsulam)、三氟噁嗪(flumezin)、氟烯草酸(flumiclorac)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、伏草隆(fluometuron)、消草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、氟苯隆(fluothiuron)、氟胺草唑(flupoxam)、flupropacil、四氟丙酸(flupropanate)、氟啶磺隆(flupyrsulfuron)、氟草同(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、呋草酮(flurtamone)、达草氟(fluthiacet)、氟磺胺草醚(fomesafen)、甲酰胺磺隆(foramsulfuron)、膦铵素(fosamine)、氟呋草醚(furyloxyfen)、草丁膦(glufosinate)、草铵膦(glufosinate-P)、草甘膦(glyphosate)、氟氯吡啶酯(halauxifen)、氟硝磺酰胺(halosafen)、吡氯磺隆(halosulfuron)、卤草定(haloxydine)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、六氯丙酮(hexachloroacetone)、六氟胂酸盐(hexaflurate)、六嗪酮(hexazinone)、咪草酯(imazamethabenz)、咪草啶酸(imazamox)、甲咪唑烟酸(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、啶咪磺隆(imazosulfuron)、茚草酮(indanofan)、indaziflam、碘草腈(iodobonil)、碘甲烷(iodomethane)、碘磺隆(iodosulfuron)、碘苯腈(ioxynil)、抑草津(ipazine)、ipfencarbazone、丙草定(iprymidam)、丁咪胺(isocarbamid)、异草定(isocil)、丁嗪草酮(isomethiozin)、异草完隆(isonoruron)、氮草(isopolinate)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁氟草酮(isoxaflutole)、噁草醚(isoxapyrifop)、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、甲基胂酸(MAA)、甲胂一铵(MAMA)、2甲4氯(MCPA)、酚硫杀(MCPA-thioethyl)、2甲4氯丁酸(MCPB)、2甲4氯丙酸(mecoprop)、精2甲4氯丙酸(mecoprop-P)、丁硝酚(medinoterb)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、灭莠津(mesoprazine)、甲基二磺隆(mesosulfuron)、甲基磺草酮(mesotrione)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、氟哒草(metflurazon)、噻唑隆(methabenzthiazuron)、氟烯硝草(methalpropalin)、灭草定(methazole)、甲硫苯威(methiobencarb)、methiozolin、灭草恒(methiuron)、醚草通(methometon)、盖草津(methoprotryne)、溴甲烷(methyl bromide)、异硫氰酸甲酯(methyl isothiocyanate)、苯丙隆(methyldymron)、色满隆(metobenzuron)、秀谷隆(metobromuron)、异丙甲草胺(metolachlor)、唑草磺胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、草达灭(molinate)、庚酰草胺(monalide)、特噁唑隆(monisouron)、单氯代乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、灭草隆(monuron)、伐草快(morfamquat)、甲胂一钠(MSMA)、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、吡氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、达草灭(norflurazon)、草完隆(noruron)、八氯酮(OCH)、坪草丹(orbencarb)、邻-二氯苯(ortho-dichlorobenzene)、orthosulfamuron、黄草消(oryzalin)、炔丙噁唑草(oxadiargyl)、噁草灵(oxadiazon)、噁杀草敏(oxapyrazon)、环丙氧磺隆(oxasulfuron)、氯噁嗪草(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、对伏隆(parafluron)、百草枯(paraquat)、克草猛(pebulate)、壬酸(pelargonic acid)、胺硝草(pendimethalin)、五氟磺草胺(penoxsulam)、五氯酚(pentachlorophenol)、甲氯酰草胺(pentanochlor)、戊噁唑草(pentoxazone)、氟草磺胺(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙基(phenmedipham-ethyl)、稀草隆(phenobenzuron)、乙酸苯汞(phenylmercury acetate)、氨氯吡啶酸(picloram)、氟吡草胺(picolinafen)、pinoxaden、哌草磷(piperophos)、亚砷酸钾(potassium arsenite)、叠氮化钾(potassiumazide)、氰酸钾(potassium cyanate)、冰草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、环氰津(procyazine)、氨氟乐灵(prodiamine)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、丙草止津(proglinazine)、扑灭通(prometon)、扑草净(prometryn)、毒草安(propachlor)、敌稗(propanil)、喔草酯(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟丙磺隆(prosulfuron)、扑灭生(proxan)、广草胺(prynachlor)、比达农(pydanon)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、pyrasulfotole、吡唑特(pyrazolynate)、吡嘧磺隆(pyrazosulfuron)、苄草唑(pyrazoxyfen)、嘧苯草肟(pyribenzoxim)、稗草丹(pyributicarb)、氯草定(pyriclor)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、pyrimisulfan、嘧硫草醚(pyrithiobac)、pyroxasulfone、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、硫氰苯乙胺(rhodethanil)、玉嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、S-异丙甲草胺(S-metolachlor)、另丁津(sebuthylazine)、密草通(secbumeton)、稀禾定(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西玛通(simeton)、西草净(simetryn)、氯乙酸(SMA)、亚砷酸钠(sodium arsenite)、叠氮化钠(sodium azide)、氯酸钠(sodium chlorate)、磺草酮(sulcotrione)、草克死(sulfallate)、磺胺草唑(sulfentrazone)、嘧磺隆(sulfometuron)、乙磺磺隆(sulfosulfuron)、硫酸(sulfuric acid)、吖庚磺酯(sulglycapin)、灭草灵(swep)、三氯醋酸(TCA)、牧草胺(tebutam)、丁唑隆(tebuthiuron)、tefuryltrione、tembotrione、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、猛杀草(terbuchlor)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、氟氧隆(tetrafluron)、噻醚草胺(thenylchlor)、赛唑隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑胺(thidiazimin)、赛二唑素(thidiazuron)、噻酮磺隆-甲基(thiencarbazone-methyl)、噻磺隆(thifensulfuron)、禾草丹(thiobencarb)、丁草威(tiocarbazil)、嘧草胺(tioclorim)、topramezone、苯草酮(tralkoxydim)、triafamone、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、杀草畏(tricamba)、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三羟基三嗪(trihydroxytriazine)、三甲隆(trimeturon)、茚草酮(tripropindan)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、灭草猛(vernolate)、和二甲苯草胺(xylachlor)。
本申请另一种实施方式为用于防治或预防真菌侵袭的方法。该方法包括向土壤、植物、根、叶子、种子、或真菌所在地(locus)或向要预防感染(infestation)的所在地(例如施用至谷物或葡萄植物)施用杀真菌有效量的一种多种式I化合物。所述化合物适于在抗真菌水平处理各种植物,同时表现出低植物毒性。所述化合物可以用于保护剂和/或铲除剂方式二者中。
发现所述化合物具有显著的杀真菌作用,特别是用于农业用途。多种所述化合物特别有效用于农业作物和园艺植物。
本领域技术人员理解的是,所述化合物针对前述真菌的效力确立了所述化合物作为杀真菌剂的一般效用。
所述化合物具有宽的抗真菌病原体(fungicidal pathogen)活性的范围。示例性病原体可包括但不限于以下病害的引发剂(causing agent):小麦斑枯病(wheat leafblotch)(禾生球腔菌(Mycosphaerella graminicola);不完整阶段(inperfect stage):小麦叶斑病病原菌(Septoria tritici)),小麦褐锈病(wheat brown rust)(小麦叶锈菌(Puccinia triticina)),小麦条锈病(wheat stripe rust)(小麦条锈菌(Pucciniastriiformis)),苹果黑星病(scab of apple)(苹果黑星病菌(Venturia inaequalis)),葡萄白粉病(powdery mildew of grapevine)(葡萄白粉病(Uncinula necator)),大麦烫伤(barley scald)(大麦云纹病菌(Rhynchosporiumsecalis)),稻瘟病(blast of rice)(稻瘟病菌(Magnaporthe grisea)),大豆锈病(rust of soybean)(豆薯层锈菌(Phakopsorapachyrhizi)),小麦颖枯病(glume blotch of wheat)(小麦颖枯病菌(Leptosphaerianodorum)),小麦白粉病(powdery mildew of wheat)(小麦白粉菌(Blumeria graminisf.sp.tritici)),大麦白粉病(powdery mildew of barley)(大麦白粉病菌(Blumeriagraminis f.sp.hordei)),瓜类白粉病(powdery mildew of cucurbits)(黄瓜白粉病(Erysiphe cichoracearum)),瓜类炭疽病(Anthracnose of cucurbits)(瓜类炭疽病(Glomerella lagenarium)),甜菜褐斑病(leaf spot of beet)(甜菜尾孢菌(Cercosporabeticola)),番茄绵疫病(early blight of eggplant)(番茄早疫病菌(Alternariasolani)),和大麦斑枯(spot blotch of barley)(禾旋孢腔菌(Cochliobolus sativus))。所施用的活性物质的确切量不仅依赖于所施用的具体活性物质而且还依赖于所需的具体作用、所防治的真菌种类及其生长阶段,以及将与所述化合物接触的植物的部分或其它产物。因此,所有化合物和含有所述化合物的制剂在相似浓度时可能不是同等有效的或不能抗相同种类的真菌。
所述化合物以病害抑制和植物学可接受的量有效用于植物。术语"病害抑制和植物学可接受的量"是指杀死或抑制植物病害(希望对其进行防治)但对植物不是明显具有毒性的化合物的量。该量通常为约0.1至约1000ppm(份每百万份),优选的是1至500ppm。所需化合物的确切浓度随所防治的真菌病害、所采用的制剂类型、施用方法、具体植物种类、气候条件等变化。合适的施用率通常在约0.10至约4磅/英亩(约0.01至0.45克/平方米,g/m2)范围内。
可将本文所给出的任意范围或所需值进行扩展或改变而不丧失所寻求的作用,这一点对技术人员理解本文教导内容来说是显而易见的。
式I化合物可使用公知的化学方法制备。在本说明书没有专门提及的中间体是商购的、可通过化学文献中披露的路线制备或可容易地使用标准方法由商业起始物质合成。
一般方案
以下方案说明生成式(I)的金属酶抑制剂化合物的方法。以下说明书和实施例用于说明目的,不应将其理解为对取代基或取代类型的限制。对于本领域技术人员显而易见的是,很多式I化合物可以使用以下方案内公开的多于一种路线合成。
式1.7的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以根据方案1,步骤c-e中所示的方法由适当取代的前体例如式1.3和1.4的化合物(其可以根据方案1,步骤a-b中所示的方法制备)制备。式1.3的化合物可以经式1.0的化合物与用铜(Cu(0))活化的2,2-二氟-2-溴乙酸乙酯在极性非质子溶剂例如二甲基亚砜(DMSO)中的缩合反应制备,如步骤a中所示。化合物1.4可以如下制备:在极性溶剂如N,N-二甲基甲酰胺(DMF)中在升高温度例如80-100℃用亲核试剂例如式1.2的化合物的酚盐阴离子(通过用碱金属碳酸盐碱例如碳酸铯(Cs2CO3)处理式1.2的苯酚生成)处理适当缺电子的式1.1的4-氟苯甲腈,如步骤b中所示。式1.5的酮可以经式1.3的化合物与适当取代的亲核试剂如锂化吡啶(其通过用正丁基锂(n-BuLi)处理式1.4的溴吡啶生成)在非质子溶剂例如甲苯中在约-78℃的降低温度的缩合反应制备,如步骤c中所示。式1.6的环氧化物可以通过在极性非质子溶剂的混合物例如四氢呋喃(THF)和DMSO的混合物中在降低温度例如约-20℃至0℃用二甲亚砜亚甲基叶立德(通过用强碱如叔丁醇钾(KOtBu)或氢化钠(NaH)处理三甲基碘化亚砜生成)处理式1.5的酮制备,如步骤d中所示。式1.7的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过在碱金属碳酸盐碱例如碳酸钾(K2CO3)存在下在极性溶剂如DMF中在约60℃的升高温度用亲核试剂例如1H-四唑处理适当取代的环氧化物例如式1.6的环氧化物制备,如步骤e中所示。
方案1
式2.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以根据方案2,步骤b-d所示的方法由适当取代的前体例如式2.1和2.2的化合物(其可以根据方案2,步骤a所示的方法制备)制备。式2.1的Weinreb酰胺可以由式2.0的丙酸使用由Trost等人(J.Am.Chem.Soc.2010,132,8915-8917)报告的方法制备,如步骤a中所示。式2.3的酮可以经由式2.1的Weinreb酰胺与亲核试剂剂如锂化吡啶(经过用n-BuLi处理适当取代的溴吡啶例如式2.2的溴吡啶生成)在非质子溶剂例如乙醚(Et2O)中在约-78℃的降低温度的缩合反应制备,如步骤b中所示。式2.4的环氧化物可以由式2.3的酮使用方案1,步骤d中所述的方法制备,如步骤c中所示。式2.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过在有机胺碱例如二异丙基胺存在下在极性非质子溶剂如DMSO中在约60℃的升高温度用亲核试剂例如1H-四唑处理适当取代的环氧化物例如式2.4的环氧化物制备,如步骤d中所示。
方案2
式3.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以根据方案3,步骤a-c所示的方法由适当取代的前体例如式3.0-3.1的化合物制备。式3.2的酮可以通过在非质子溶剂如甲苯中在约0℃至23℃的温度用格氏试剂(例如用异丙基氯化镁(i-PrMgCl)处理式3.2的溴吡啶进行转移金属化所制备的格氏试剂)处理式3.0的Weinreb酰胺制备,如步骤a中所示。式3.4的4-三氟甲基苯基醚由式3.2的酮通过用式3.3的酚在碱金属碳酸盐碱例如Cs2CO3存在下在极性溶剂例如DMF中在约110℃的升高温度进行处理制备,如步骤b中所示。式3.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以通过在氯化锌(ZnCl2)和氯化锂(LiCl)存在下在极性非质子溶剂如THF中在约0℃的降低温度用亲核试剂例如格氏试剂如i-PrMgCl处理适当取代的酮例如式3.4的酮制备,如由Hatano等人所述(J.Am.Chem.Soc.2006,128,9998-9999)且如步骤c中所示。
方案3
式4.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以根据方案4,步骤a-d所示的方法由适当取代的前体例如式4.0合3.2的化合物制备。式4.1的酮可以通过按方案3,步骤a中所述处理式4.0的Weinreb酰胺和式3.1的溴吡啶制备,如步骤a中所示。式4.3的酮可以按方案3,步骤b中所述由式4.1的酮和式4.2的酚制备,如步骤b中所示。式4.4的环氧化物可以由式4.3的酮使用方案1,步骤d中所述的方法制备,如步骤c中所示。式4.5的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过在有机胺碱例如二异丙基胺存在下在极性非质子溶剂如DMF在约70℃的升高温度用亲核试剂例如1H-四唑处理适当取代的环氧化物例如式4.4的环氧化物制备,如步骤d中所示。
方案4
式5.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以按照方案5,步骤a所示如下制备:在极性非质子溶剂如THF中在约0℃的降低温度用亲核试剂例如适当取代的格氏试剂处理适当取代的酮例如式5.0的酮。格氏试剂可以由(氯甲基)环丙烷和镁(Mg)在催化剂碘(I2)存在下在极性非质子溶剂如THF中在约65℃的升高温度制备。
方案5
式6.8的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以按照方案6,步骤c-d所示由适当取代的前体例如式6.0-6.4的化合物(其可以根据方案6,步骤a-b所示的方法制备)制备,式6.5的化合物可以使用由等人报告的方法(Tet.Lett.1998,39,1717-1720)制备,该方法描述式6.3的膦酸酯化合物的制备及其之后用于与式6.4的嘧啶甲醛的Horner-Emmons缩合反应,如步骤a和b中所示。式6.7的化合物可以经由在碱金属碳酸盐碱例如碳酸钠(Na2CO3)和钯催化剂例如[1,1′-双(二苯基膦基)二茂铁]二氯钯[PdCl2(dppf)]存在下在混合溶剂系统中在约85℃的升高温度式6.5的溴吡啶和适当取代的硼酸或硼酸酯例如式6.6的硼酸之间的Suzuki偶联反应制备,所述混合溶剂系统例如为极性非质子溶剂如二氧杂环己烷或乙腈(CH3CN)与水的混合物,其中组合物中有机溶剂与水的比率为约3:1,如步骤c中所示。式6.8的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过在极性非质子溶剂如THF中在约-78℃的降低温度用亲核试剂例如格氏试剂如甲基溴化镁(MeMgBr)处理适当取代的酮例如式6.7的酮制备,如步骤d中所示。
方案6
式7.6的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以按照方案7,步骤a-e所示制备。式7.2的溴吡啶可以经由在碱金属碳酸盐碱例如K2CO3和钯催化剂例如四(三苯基膦)钯(0)[Pd(PPh3)4]存在下在混合溶剂系统中适当取代的芳基卤化物如式7.0的碘苯和硼酸或硼酸酯如式7.1的吡啶硼酸之间的Suzuki偶联反应制备,所述混合溶剂系统例如为极性非质子溶剂如DMF、二氧杂环己烷、或CH3CN与水的混合物,其中组合物中有机溶剂与水的比率为约4:1。该反应在约120℃的升高温度进行,这样的温度可以通过常规加热技术或经微波辐射实现,如步骤a中所示。式7.3的仲醇可以经由金属化化学制备,其中式7.2的溴吡啶和过量特戊醛的混合物用n-BuLi在约-78℃的降低温度在芳族烃如甲苯中进行处理,如步骤b中所示。式7.4的酮可以通过在卤代烃例如二氯甲烷(CH2Cl2,DCM)中在约0℃的降低温度用1,1,1-三乙酰氧-1,1-二氢-1,2-苯碘酰-3(1H)-酮(戴斯-马丁高碘烷)处理式7.3的仲醇制备,如步骤c中所示。式7.5的环氧化物可以由式7.4的酮使用方案1,步骤d中所述的方法制备,如步骤d中所示。式7.6的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过在碱金属碳酸盐碱例如K2CO3存在下在极性非质子溶剂如DMSO中在约70℃的升高温度用亲核试剂例如1H-四唑处理适当取代的环氧化物例如式7.5的环氧化物制备,如步骤e中所示。
方案7
式8.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以按照方案8,步骤a-b所示制备。式8.0的酮可以按照方案3,步骤a中所述制备。式8.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以通过在ZnCl2和LiCl存在下在极性非质子溶剂如THF中在约0℃的降低温度用亲核试剂例如格氏试剂如叔丁基氯化镁(tBuMgCl)处理适当取代的酮例如式8.0的酮制备,如步骤b中所示。
方案8
式9.4的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以按照方案9,步骤a-e中所示制备。式9.0的吡啶基甲醛可以经由金属化化学制备,其中式7.2的溴吡啶在芳族烃如甲苯中的溶液用n-BuLi在约-78℃的降低温度进行处理,将所得的锂化吡啶用无水DMF淬灭,如步骤a中所示。式9.1的仲醇可以通过在非质子溶剂如Et2O中用亲核试剂剂如格氏试剂处理式9.0的醛在非质子溶剂如Et2O中的溶液制备,所述格氏试剂可以通过用Mg粉处理适当取代的苄基溴例如4-氯-2-氟苄基溴制备,如步骤b中所示。式9.2的酮可以经由使用戴斯-马丁高碘烷在方案7,步骤c中所述的条件下对式9.1的仲醇进行氧化来制备,如步骤c中所示。式9.3的环氧化物可以由式9.2的酮使用方案1,步骤d中所述的方法(如步骤d中所示)但是使用醇例如叔丁醇(tBuOH)作为反应溶剂制备。式9.4的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以通过使用方案7,步骤e中所述的条件用亲核试剂例如1H-四唑处理适当取代的环氧化物例如式9.3的环氧化物制备,如步骤e中所示。
方案9
式10.0和10.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以按照方案10,步骤a中所示制备。式10.0的炔烃可以通过在约0℃的降低温度用适当取代的亲核试剂剂如乙炔化物阴离子处理适当取代的酮例如式5.0的酮在极性非质子溶剂如THF中的溶液制备。乙炔化物阴离子可以通过在极性非质子溶剂如THF中在添加格氏试剂期间的约0℃至在添加以后的约40℃的温度用格氏试剂例如乙基溴化镁(EtMgBr)处理适当取代的端炔基例如3,3二甲基丁-1-炔制备。式10.1的化合物是残留的格氏试剂即EtMgBr简单加成到式5.0的酮中的产物,如方案5,步骤a中所述。
方案10
式11.0的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以按照方案10,步骤a中所示如下制备:在约0℃的降低温度,用适当取代的亲核试剂例如格氏试剂处理适当取代的酮例如式5.0的酮在非质子溶剂如Et2O中的溶液。格氏试剂可以通过在非质子溶剂如Et2O中在约23℃至约35℃的温度用Mg处理适当取代的苄基溴例如1-(溴甲基)-4-氯-2-氟苯制备。
方案11
式12.8的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以根据方案12,步骤c-f所示的方法由适当取代的前体例如式12.0-12.3的化合物(其可以根据方案12,步骤a-b所示的方法制备)制备。式12.2的醚可以通过在极性非质子溶剂如DMSO中在约120℃的升高温度用碱金属碳酸盐碱例如K2CO3处理适当缺电子的式12.0的4-氟苯甲腈与适当取代的酚如式12.1的酚的混合物制备,如步骤a中所示。式12.3的醛可以通过在约-78℃的降低温度用还原剂例如二异丁基氢化铝(DIBAL-H)处理式12.2的腈在极性非质子溶剂如THF中的溶液制备,如步骤b中所示。式12.5的仲醇可以通过在约0℃的降低温度用适当取代的亲核试剂例如格氏试剂处理式12.3的醛在非质子溶剂如Et2O中的溶液制备,其中所述格氏试剂通过在非质子溶剂如Et2O中在约23℃至约35℃的温度用Mg处理适当取代的苄基溴例如1-(溴甲基)-4-氯-2-氟苯(式12.4)制备,如步骤c中所示。式12.6的酮可以经由使用戴斯-马丁高碘烷在方案7,步骤c中所述的条件下对式12.5的仲醇进行氧化来制备,如步骤d中所示。式12.7的环氧化物可以通过在约0℃的降低温度用重氮甲烷处理式12.6的酮在非质子溶剂如Et2O中的溶液制备,如步骤e中所示。式12.8的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以按照方案7,步骤e中所述的方法制备,如步骤f中所示。
方案12
式13.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以经方案13,步骤a中所示的金属化方法如下制备:在约-78℃的降低温度用n-BuLi处理适当取代的酮例如式13.0的酮和适当取代的芳基卤化物例如5-溴嘧啶在非质子溶剂如THF的溶液的混合物。
方案13
式14.0的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为1)可以按照方案14,步骤a中所示如下制备:在约0℃的降低温度用氟化物源如氟化铯(CsF)处理适当取代的酮例如式6.7的酮和三甲基-(三氟甲基)硅烷在非质子溶剂如THF中的溶液的混合物,然后用无机酸如氯化氢水溶液(HCl)进行水解。
方案14
式15.0的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)可以经方案15,步骤a中所示的金属化方法如下制备:在约-78℃的降低温度用适当取代的亲核试剂处理适当取代的酮例如式8.0的酮在非质子溶剂如Et2O中的溶液,所述亲核试剂例如为通过在约-78℃的降低温度用n-BuLi处理适当取代的芳基溴例如1-溴-2,4-二氟苯在非质子溶剂如Et2O中的溶液制备的苯基锂。
方案15
式16.3的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)是代表性的式I的金属酶抑制剂,并且可以根据方案16,步骤a-c所示的方法制备。式16.1的酮可以通过按照方案3,步骤a中所述在约-40℃至23℃的温度在极性非质子溶剂如THF中处理式3.0的Weinreb酰胺和式16.0的碘溴吡啶制备。式16.2的醇可以通过在约-78℃至0℃的温度在极性非质子溶剂如THF中用亲核试剂例如格氏试剂如叔戊基氯化镁处理式16.1的酮制备,如步骤b中所示。或者,利用烷基锂或芳基锂的金属化化学也可以用于得到由式16.2所表示的醇,如方案15,步骤a中所述。式16.3的醇可以由式16.2的醇和硼酸、硼酸酯、或N-甲基亚氨基二乙酸(MIDA)硼酸酯使用方案7,步骤a中所述的Suzuki偶联方法、或使用Angew.Chem.Int.Ed.2012,51,2667中所述的改良的Suzuki偶联过程制备,如步骤c中所示。
方案16
式17.1和17.2的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)是代表性的式I的金属酶抑制剂,并且可以根据方案17,步骤a所示的方法制备。E和Z肟异构体(分别为式17.1和17.2的化合物)可以通过在极性质子溶剂如甲醇(MeOH)中在约22℃用碱例如乙酸钠(NaOAc)和胺例如O-甲基羟胺盐酸盐处理式17.0的酮制备,如步骤a中所示。
方案17
式18.1的化合物(其中R1-R3、R5-R7、和Z按原始限定,n为0)是代表性的式I的金属酶抑制剂,并且可以根据方案18所示的方法制备。式18.1的化合物可以通过在卤代烃如DCM中在约23℃的温度用碘化试剂例如氯碘甲烷(CH2ClI)处理式18.0的化合物制备,如步骤a中所示。
方案18
实施例
实施例1:制备4-((6-(1-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1H-四唑-1-基)丙-2-基)吡啶-3-基)氧基)苯甲腈(1)。
步骤A1:制备2-(2,4-二氟苯基)-2,2-二氟乙酸乙酯。
向铜金属(Cu,10.59克(g),166.6毫摩尔(mmol))在无水DMSO(80毫升(mL))的搅拌悬浮液中添加2,2-二氟-2-溴乙酸乙酯(16.9g,83.3mmol),将溶液在室温搅拌90分钟(min)。向该溶液中添加2,4-二氟碘苯(10.0g,41.7mmol)在DMSO(10mL)中的溶液,将反应混合物在室温搅拌48小时(h)。将反应混合物用乙酸乙酯(EtOAc,800mL)稀释,过滤通过层,并将滤液先后用5%氢氧化铵水溶液(NH4OH)、氯化铵(NH4Cl)饱和水溶液、和氯化钠(NaCl,盐水)饱和水溶液洗涤。将有机相用硫酸钠(Na2SO4)干燥,过滤,并减压浓缩,得到粗产物,将粗产物通过柱色谱纯化(硅胶,SiO2),得到标题化合物(7.9g,80%)。
步骤A2:制备4-(6-溴吡啶-3-基氧基)苯甲腈。
在室温在氮气(N2)气氛下向2-溴-5-羟基吡啶(10.0g,62.1mmol)和4-氟苯甲腈(11.21g,93.10mmol)在DMF(125mL)的搅拌悬浮液中添加Cs2CO3(40.44g,124.1mmol),将反应混合物加热至90℃并在90℃搅拌16h。将反应混合物冷却至室温,用冰水稀释,并用EtOAc萃取。将合并的有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩,得到粗产物,将粗产物通过柱色谱纯化(SiO2),得到标题化合物(9.5g,55%)。
步骤B:制备4-(6-(2-(2,4-二氟苯基)-2,2-二氟乙酰基)吡啶-3-基氧基)苯甲腈。
在-78℃历时10min的时间段向4-(6-溴吡啶-3-基氧基)苯甲腈(1g,3.63mmol)在无水甲苯(10mL)的搅拌悬浮液中逐滴添加n-BuLi在己烷中的溶液(2.5摩尔浓度(M),4.36mL,10.9mmol),将混合物在-78℃搅拌2h。将反应混合物用2-(2,4-二氟苯基)-2,2-二氟乙酸乙酯(1.71g,7.26mmol)在甲苯(10mL)中的溶液处理,将混合物缓慢升温至室温并搅拌16h。将反应混合物用1当量浓度(N)的HCl水溶液淬灭,并用EtOAc萃取。将有机萃取物用Na2SO4干燥,过滤,并减压浓缩,得到标题化合物(1.75g),其无需进一步纯化即可用于下一步骤。
步骤C:制备4-(6-(2-(2,4-二氟苯基)二氟甲基)环氧乙-2-基)吡啶-3-基氧基)苯甲腈。
向三甲基碘化亚砜(660毫克(mg),3.02mmol)在无水THF(10mL)和DMSO(4mL)的混合物的0℃搅拌悬浮液中添加叔丁醇钾(KOtBu,339mg,3.02mmol),将混合物在0℃搅拌90min。将反应冷却至-20℃,历时10min的时间段将4-(6-(2-(2,4-二氟-苯基)-2,2-二氟乙酰基)吡啶-3-基氧基)苯甲腈(0.9g,2.32mmol)在THF(19mL)中的溶液逐滴添加到该混合物中。将反应混合物升温至0℃,在0℃搅拌30min,并用1N HCl溶液和之后的碳酸氢钠(NaHCO3)饱和水溶液淬灭。将混合物用EtOAc萃取,将有机相用Na2SO4干燥,过滤,并减压浓缩,得到粗产物,将粗产物通过柱色谱纯化(SiO2),得到标题化合物(150mg,10%)。
步骤D:制备4-((6-(1-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1H-四唑-1-基)丙-2-基)吡啶-3-基)氧基)苯甲腈(1)。
向4-(6-(2-(2,4-二氟苯基)二氟甲基)环氧乙-2-基)吡啶-3-基氧基)苯甲腈(150mg,0.2mmol)在DMF(2mL)的搅拌溶液中添加1H-四唑(26mg,0.3mmol)和K2CO3(51mg,0.3mmol),将反应混合物在60℃搅拌16h。将反应混合物冷却至室温,用冰水淬灭,并用EtOAc萃取。将合并的有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩,将所得粗残余物通过柱色谱纯化(SiO2),得到作为浅黄色半固体的标题化合物(35mg,20%):参见表2的表征数据。
实施例2:制备2-(5-((5-氯吡啶-2-基)氧基)吡啶-2-基)-4-(2,4-二氟苯基)-1-(1H-四唑-1-基)丁-2-醇(2)。
步骤A:制备3-(2,4-二氟苯基)-N-甲氧基-N-甲基丙酰胺。
遵照由Trost,B.M.等人描述的改编过程(Journal of the American ChemicalSociety(2010),132(26),8915-8917)。在惰性气氛(N2)下在0℃向3-(2,4-二氟苯基)丙酸(1.0g,5.37mmol)和两滴DMF在无水THF(10.8mL)的磁力搅拌的混合物中逐滴添加草酰氯(0.564mL,6.45mmol)。将反应混合物在0℃搅拌1h,然后通过在减压下旋转蒸发移除挥发性组分。将所得油状物溶解于CH2Cl2,再次通过旋转蒸发移除挥发性组分。在包含悬浮在CH2Cl2(5.40mL)的N,O-二甲基羟胺盐酸盐(0.576g,5.91mmol)的单独20mL小瓶中添加吡啶(1.086mL,13.43mmol),将反应混合物冷却至0℃。将新鲜制备的酰氯溶解于CH2Cl2(5.40mL),历时3min的时间段将该溶液添加到混合物中。立即形成白色沉淀物,在逐渐升温至室温的同时搅拌反应。在2h之后,将反应混合物用EtOAc稀释,并先后用2N HCl、NaHCO3饱和水溶液(2x)、和盐水洗涤,然后通过使其穿过相分离器滤芯来干燥。通过旋转蒸发移除溶剂和其它挥发性组分,得到作为淡黄色油状物的标题化合物(1.195g,97%):1H NMR(400MHz,CDCl3)δ7.25-7.18(m,1H),6.83-6.74(m,2H),3.63(s,3H),3.17(s,3H),2.95(t,J=7.7Hz,2H),2.72(t,J=7.6Hz,2H);19F NMR(376MHz,CDCl3)δ-113.29,-114.40(d,J=6.7Hz);ESIMS m/z 230[M+H]+。
步骤B:制备1-(5-((5-氯吡啶-2-基)氧基)吡啶-2-基)-3-(2,4-二氟苯基)丙-1-酮。
历时1min的时间段向2-溴-5-((5-氯吡啶-2-基)氧基)吡啶(243mg,0.851mmol)在无水Et2O(2908微升(μL))的-78℃的磁力搅拌混合物中逐滴添加n-BuLi在己烷中的溶液(2.0M,425μL,0.850mmol)。将反应混合物在-78℃搅拌40-60min,然后逐滴用3-(2,4-二氟苯基)-N-甲氧基-N-甲基丙酰胺(150mg,0.654mmol)在Et2O(1454μL)中的溶液进行处理。在1h之后,通过逐滴添加1N HCl(5mL)将反应淬灭,然后将其升温至室温。将反应用(5mL)稀释,然后使各相分离。将水相用另外的Et2O(2x)萃取,通过使合并的有机物穿过相分离器滤芯来使其干燥,将其在温和的N2流下浓缩。将所得残余物通过柱色谱纯化(SiO2,0→20%EtOAc在己烷中),得到作为灰白色固体的标题化合物(76mg,31.0%):1H NMR(400MHz,CDCl3)δ8.50(dd,J=2.7,0.5Hz,1H),8.13-8.10(m,2H),7.73(dd,J=8.7,2.7Hz,1H),7.61(dd,J=8.6,2.7Hz,1H),7.26-7.21(m,1H),7.02(dd,J=8.7,0.6Hz,1H),6.82-6.74(m,2H),3.53(t,J=7.5Hz,2H),3.06(t,J=7.5Hz,2H);19F NMR(376MHz,CDCl3)δ-113.54(d,J=6.8Hz),-113.99(d,J=6.8Hz);ESIMS m/z 375[M+H]+。
步骤C:制备5-氯-2-((6-(2-(2,4-二氟苯乙基)环氧乙-2-基)吡啶-3-基)氧基)吡啶。
在N2气氛下向三甲基碘化亚砜(103mg,0.468mmol)在THF(961μL)的磁力搅拌的混合物中添加NaH(18.73mg,0.468mmol,60%在矿物油中的分散体),将混合物在室温搅拌1h。将反应混合物冷却至0℃,并用1-(5-((5-氯吡啶-2-基)氧基)吡啶-2-基)-3-(2,4-二氟苯基)丙-1-酮(150mg,0.360mmol)在THF(961μL)中的溶液逐滴进行处理。在2.5h之后,通过逐滴添加NH4Cl饱和水溶液将反应淬灭,将混合物用Et2O(3x)萃取。通过使合并的有机萃取物穿过相分离器滤芯来使其干燥,将其在温和的N2流下浓缩。将所得残余物通过柱色谱纯化(SiO2,0→30%EtOAc在己烷中),得到作为无色油状物的标题化合物(56mg,40.0%):1H NMR(400MHz,CDCl3)δ8.44(dd,J=2.7,0.6Hz,1H),8.10(d,J=2.6Hz,1H),7.72-7.67(m,1H),7.48(dd,J=8.6,2.7Hz,1H),7.39(dd,J=8.6,0.4Hz,1H),7.18-7.10(m,1H),6.97(d,J=8.7Hz,1H),6.80-6.70(m,2H),3.06(d,J=5.2Hz,1H),2.85(d,J=5.2Hz,1H),2.83-2.75(m,2H),2.71(t,J=9.8Hz,1H),2.14-2.07(m,1H);19F NMR(376MHz,CDCl3)δ-113.69(dd,J=6.6,2.1Hz),-114.18(d,J=6.7Hz);ESIMS m/z 389[M+H]+。
步骤D:制备2-(5-((5-氯吡啶-2-基)氧基)吡啶-2-基)-4-(2,4-二氟苯基)-1-(1H-四唑-1-基)-丁-2-醇(2)。
向5-氯-2-((6-(2-(2,4-二氟苯乙基)环氧乙-2-基)吡啶-3-基)氧基)吡啶(56mg,0.144mmol)在DMSO(480μL)的磁力搅拌的混合物中添加二异丙基胺和1H-四唑的混合物(1:1)(123mg,0.720mmol),将反应混合物升温至60℃并在60℃搅拌2-3天(d)。通过添加水将反应淬灭,将其用CH2Cl2(3x)萃取。通过使合并的有机萃取物穿过相分离器滤芯来使其干燥,将其在温和的N2流下浓缩。将所得残余物通过柱色谱纯化(SiO2,20→60%EtOAc在己烷中),得到产物的两种异构体。分离的标题化合物(37.0mg,56%)为白色固体:参见表2的表征数据。
2H-异构体,即2-(5-((5-氯吡啶-2-基)氧基)吡啶-2-基)-4-(2,4-二氟苯基)-1-(2H-四唑-2-基)丁-2-醇(19.0mg,28.7%)分离为无色油状物:1H NMR(400MHz,CDCl3)δ8.43(s,1H),8.37(d,J=2.6Hz,1H),8.11(d,J=2.6Hz,1H),7.71(dd,J=8.7,2.7Hz,1H),7.55(dd,J=8.6,2.6Hz,1H),7.42(dd,J=8.6,0.6Hz,1H),7.04(td,J=8.7,6.6Hz,1H),6.97(d,J=8.7Hz,1H),6.77-6.67(m,2H),5.19(s,1H),5.04(s,2H),2.80-2.70(m,1H),2.43-2.30(m,2H),2.12(ddd,J=13.4,11.9,4.9Hz,1H);19F NMR(376MHz,CDCl3)δ-113.36(d,J=6.7Hz),-114.44(d,J=6.7Hz);ESIMS m/z 459[M+H]+。
实施例3:制备2-甲基-1-(嘧啶-5-基)-1-(5-(4-(三氟甲基)-苯氧基)吡啶-2-基)丙-1-醇(3)。
步骤A:制备(5-氟吡啶-2-基)(嘧啶-5-基)甲酮。
向装备有磁力搅拌棒的圆底烧瓶中添加2-溴-5-氟吡啶(2.063g,11.72mmol),将烧瓶用N2吹洗。添加无水甲苯(11.17mL),将反应在冰浴中冷却至0℃。将反应用i-PrMgCl在THF中的溶液(2.0M,5.86mL,11.7mmol)逐滴进行处理,将混合物在0℃搅拌10min,升温至室温,并在室温搅拌1.5h。将所得深棕色混合物冷却至0℃,用N-甲氧基-N-甲基嘧啶-5-甲酰胺(1.4g,8.37mmol)在无水甲苯(5.58mL)中的溶液处理,在0℃搅拌3h,将所得绿-棕色混合物在其还冷时用NH4Cl饱和水溶液(20mL)淬灭。使各相分离,将水相用EtOAc(2x 20mL)萃取。将合并的有机物用硫酸镁(MgSO4)干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为灰白色松软固体的标题化合物(492mg,32%):IR(薄膜)1678,1577cm-1;1H NMR(400MHz,CDCl3)δ9.50(s,2H),9.38(s,1H),8.59(dd,J=2.8,0.6Hz,1H),8.32(ddd,J=8.8,4.6,0.6Hz,1H),7.66(ddd,J=8.8,7.9,2.8Hz,1H);19F NMR(376MHz,CDCl3)δ-117.71;HRMS-ESI(m/z)[M+H]+,对于C10H7FN3O,计算值为204.0568;实测值为204.0567。
步骤B:制备嘧啶-5-基(5-(4-(三氟甲基)苯氧基)吡啶-2-基)甲酮。
将(5-氟吡啶-2-基)(嘧啶-5-基)甲酮(200mg,0.984mmol)、4-(三氟甲基)苯酚(160mg,0.984mmol)、和Cs2CO3(337mg,1.034mmol)在DMF(1969μL)的磁力搅拌的混合物加热至110℃并搅拌18h。将反应冷却至室温,在水(3mL)和EtOAc(3mL)之间分配,使各相分离。将水相用另外的EtOAc(2x 3mL)萃取,将合并的有机萃取物用盐水(2x 3mL)洗涤,用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→60%EtOAc在己烷中),得到作为微黄色固体的标题化合物(290mg,84%):IR(薄膜)3383,1667,1573,1319,1234cm-1;1H NMR(400MHz,CDCl3)δ9.51(s,2H),9.37(s,1H),8.50(dd,J=2.8,0.6Hz,1H),8.28(dd,J=8.7,0.6Hz,1H),7.78-7.68(m,2H),7.49(dd,J=8.7,2.8Hz,1H),7.25-7.19(m,2H);19F NMR(376MHz,CDCl3)δ-62.13;HRMS-ESI(m/z)[M+H]+,对于C17H11F3N3O2,计算值为346.0798;实测值为346.0780。
步骤C:制备2-甲基-1-(嘧啶-5-基)-1-(5-(4-(三氟甲基)-苯氧基)吡啶-2-基)丙-1-醇(3)。
向装备有磁力搅拌棒的小瓶中添加ZnCl2(10.66mg,0.078mmol)和LiCl(12.16mg,0.287mmol),将小瓶封上盖子并用N2吹洗。在N2下逐滴添加i-PrMgCl在THF中的溶液(2.0M,222μL,0.443mmol),将反应在室温搅拌1h。将所得均匀的棕色溶液在冰浴中冷却至0℃,缓慢添加嘧啶-5-基(5-(4-(三氟甲基)苯氧基)吡啶-2-基)甲酮(90mg,0.261mmol)在无水THF(2738μL)中的溶液,将反应在0℃搅拌4h。将所得红-棕色反应混合物在其还冷时用NH4Cl饱和水溶液(3mL)淬灭,将混合物用EtOAc(3x 5mL)萃取。将合并的萃取物用MgSO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,0→70%EtOAc在己烷中),得到作为微黄色粘性油状物的标题化合物(64mg,62%):参见表2的表征数据。
实施例4:制备4-((6-(1-环丙基-1-羟基-2-(1H-四唑-1-基)乙基)吡啶-3-基)氧基)苯甲腈(19)。
步骤A:制备环丙基(5-氟吡啶-2-基)甲酮。
根据实施例3A中描述的条件由2-溴-5-氟吡啶和N-甲氧基-N-甲基-环丙烷甲酰胺制备标题化合物,其以73%收率分离为黄色油状物:IR(薄膜)1681,1580,1400,1370cm-1;1HNMR(400MHz,CDCl3)δ8.55(d,J=2.8Hz,1H),8.10(ddd,J=8.7,4.7,0.6Hz,1H),7.52(ddd,J=8.7,8.0,2.8Hz,1H),3.55-3.39(m,1H),1.28-1.22(m,2H),1.15-1.08(m,2H);19F NMR(376MHz,CDCl3)δ-120.55(d,J=1.5Hz);EIMS(m/z)165。
步骤B:制备4-((6-(环丙烷羰基)吡啶-3-基)氧基)苯甲腈。
根据实施例3B中描述的条件由环丙基(5-氟吡啶-2-基)甲酮和4-羟基苯甲腈制备标题化合物。其以83%收率分离为淡黄色固体:IR(薄膜)2228,1676,1576,1499,1246cm-1;1H NMR(400MHz,CDCl3)δ8.50(dd,J=2.7,0.7Hz,1H),8.10(dd,J=8.6,0.7Hz,1H),7.75-7.67(m,2H),7.45(dd,J=8.6,2.8Hz,1H),7.16-7.10(m,2H),3.47(tt,J=7.9,4.7Hz,1H),1.30-1.21(m,2H),1.15-1.09(m,2H);HRMS-ESI(m/z)[M+H]+,对于C16H13N2O2,计算值为265.0972;实测值为265.0957。
步骤C:制备4-((6-(环丙基(羟基)(嘧啶-5-基)甲基)吡啶-3-基)氧基)苯甲腈。
向装备有磁力搅拌棒的小瓶中添加三甲基碘化亚砜(100mg,0.454mmol),DMSO(841μL),和无水THF(841μL)。向所得混合物中添加NaH(60%在矿物油中的分散体,18.2mg,0.454mmol),将反应在室温搅拌1h。在停止形成气体之后,将混浊的白色混合物冷却至0℃并用4-((6-(环丙烷羰基)吡啶-3-基)氧基)-苯甲腈(100mg,0.378mmol)在无水THF(841μL)中的溶液逐滴进行处理。将所得混浊的淡黄色混合物缓慢冷却至室温,将反应用水(3mL)淬灭和用EtOAc(3mL)稀释。使各相分离,将水相进一步用EtOAc(3x 3mL)萃取。合并的有机萃取物用MgSO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,0→15%EtOAc在己烷中),得到作为淡黄色粘性油状物的标题化合物(72mg,65%):IR(薄膜)2228,1502,1479,1247cm-1;1H NMR(400MHz,CDCl3)δ8.43(dd,J=2.8,0.7Hz,1H),7.68-7.61(m,2H),7.54(dd,J=8.6,0.7Hz,1H),7.38(dd,J=8.6,2.8Hz,1H),7.08-7.01(m,2H),3.00(dd,J=5.8,0.6Hz,1H),2.95(d,J=5.7Hz,1H),1.85(tt,J=8.4,5.3Hz,1H),0.67-0.58(m,1H),0.58-0.49(m,1H),0.49-0.38(m,2H);HRMS-ESI(m/z)[M+H]+,对于C17H15N2O2,计算值为279.1128;实测值为279.1105。
步骤D:4-((6-(1-环丙基-1-羟基-2-(1H-四唑-1-基)乙基)吡啶-3-基)氧基)-苯甲腈(19)。
向装备有磁力搅拌棒的小瓶中添加4-((6-(2-环丙基环氧乙-2-基)吡啶-3-基)氧基)苯甲腈(69mg,0.248mmol),四唑-1-二异丙基铵(212mg,1.24mmol),和DMF(1653μL)。将反应混合物升温至70℃,在70℃搅拌13h,冷却至室温,并在水(5mL)和EtOAc(5mL)之间分配。使各相分离,将水相进一步用EtOAc(3x 3mL)萃取。将合并的有机物用MgSO4干燥,过滤,浓缩,并通过柱色谱纯化(SiO2,0→75%EtOAc在己烷中),得到作为灰白色粘性半固体的标题化合物(11mg,12%):参见表2的表征数据。
实施例5:制备1-(5-(4-氯苯氧基)吡啶-2-基)-1-(嘧啶-5-基)戊-4-烯-1-醇(21)。
向装备有磁力搅拌棒的烘箱干燥的小瓶中添加Mg(6.36mg,0.262mmol),将小瓶抽空并回充N2。添加无水THF(818μL),然后添加I2晶体和(氯甲基)环丙烷(22.68μL,0.245mmol)。将混合物加热至回流,并在N2下搅拌1.5h。向单独小瓶中添加(5-(4-氯苯氧基)吡啶-2-基)(嘧啶-5-基)甲酮(51mg,0.164mmol)和无水THF(1mL),将混合物冷却至0℃。历时8min的时间段向该溶液中逐滴添加新鲜制备的格氏试剂溶液,将反应混合物在0℃搅拌3h,在其还冷时用NH4Cl饱和水溶液(2mL)淬灭,并升温至室温。将混合物用EtOAc(3x2mL)萃取,将合并的萃取物用MgSO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,0→70%EtOAc在己烷中),得到作为淡黄色粘性半固体的标题化合物(22mg,35%):参见表2的表征数据。
实施例6:制备2-[5-(4-氯苯基)-2-吡啶基]-1-嘧啶-5-基-丙-2-醇(25)。
步骤A:制备((5-溴吡啶-2-基)(苯基氨基)甲基)-膦酸二苯酯。
遵照由Journet,M.等人描述的改编过程(Tetrahdron Letters(1998),39(13),1717-1720)。向5-溴吡啶甲醛(1g,5.38mmol)在异丙醇(IPA,13.44mL)的磁力搅拌的混合物中添加苯胺(0.589mL,6.45mmol),然后添加亚磷酸二苯酯(1.665mL,8.60mmol),将反应混合物在25℃搅拌。在将苯胺添加到部分溶解于IPA的醛中之后,反应形成厚的白色沉淀物,在添加亚磷酸酯之后该沉淀物溶解,得到均匀的黄色溶液,将该溶液搅拌18h。关闭搅拌器,将反应混合物在冰浴中冷却。通过真空过滤分离出所得细的白色沉淀物,将其用冰冷的IPA洗涤几次。将固体在真空烘箱中在室温干燥4h,得到作为白色固体的标题化合物(2.501g,94%):mp 124-127℃:1H NMR(400MHz,CDCl3)δ8.65(d,J=2.3Hz,1H),7.76(ddd,J=8.4,2.3,0.7Hz,1H),7.48-7.45(m,1H),7.30-7.22(m,4H),7.19-7.11(m,4H),7.09(qd,J=2.5,1.3Hz,2H),7.06-7.01(m,2H),6.80-6.74(m,1H),6.71(dd,J=8.6,0.9Hz,2H),5.35-5.23(m,2H);13C NMR(101MHz,CDCl3)δ153.41,150.59,150.56,150.22,150.14,145.93,145.80,139.42,139.40,129.71,129.33,125.44,125.32,124.42,124.38,120.63,120.58,120.32,120.28,119.25,114.31,58.37,56.83。
步骤B:制备1-(5-溴吡啶-2-基)-2-(嘧啶-5-基)乙酮。
在惰性气氛(N2)下向((5-溴吡啶-2-基)(苯基氨基)-甲基)膦酸二苯酯(400mg,0.808mmol)、和嘧啶-5-甲醛(96mg,0.888mmol)在THF(1615μL)和IPA(404μL)的混合物的磁力搅拌的混合物中添加Cs2CO3(342mg,1.050mmol)。将反应混合物在25℃搅拌16.5h,然后用3N HCl(0.81mL,2.42mmol)逐滴进行处理,这会使气体温和形成。在2h后,通过添加5%w/v的NaOH水溶液将反应混合物的pH调节至9,将其用EtOAc(3x)萃取。通过使合并的有机萃取物穿过相分离器滤芯来使其干燥,将挥发性组分在温和的N2流下蒸发。将所得残余物用冰冷的EtOAc粉碎,得到作为淡棕色固体的标题化合物(149mg,66.3%):1H NMR(400MHz,CDCl3)δ9.14(s,1H),8.79(d,J=1.7Hz,1H),8.72(s,2H),8.02(dd,J=8.4,2.2Hz,1H),7.96(d,J=8.2Hz,1H),4.52(s,2H);13C NMR(101MHz,CDCl3)δ196.19,157.96,157.40,150.47,150.37,139.98,128.33,126.16,123.66,38.86;ESIMS m/z 278[M+H]+,m/z 276([M-H]-)。
步骤C:制备1-(5-(4-氯苯基)吡啶-2-基)-2-(嘧啶-5-基)乙酮。
在惰性气氛(N2)下向1-(5-溴吡啶-2-基)-2-(嘧啶-5-基)乙酮(200mg,0.719mmol)、(4-氯苯基)硼酸(141mg,0.899mmol)和Na2CO3(229mg,2.16mmol)在二氧杂环己烷(2697μL)和水(899μL)的混合物的磁力搅拌的混合物中添加[1,1′-双(二苯基膦基)二茂铁]二氯钯(PdCl2(dppf),52.6mg,0.072mmol)。将反应混合物加热至85℃并在85℃搅拌17h,冷却至室温,用CH3CN稀释,使其过滤通过层,将滤液在温和的N2流下蒸发。将所得残余物通过柱色谱纯化(SiO2,30→75%EtOAc在己烷中),得到作为灰白色固体的标题化合物(116mg,52.1%):mp 150-155℃;1H NMR(400MHz,CDCl3)δ9.14(s,1H),8.92(dd,J=2.3,0.8Hz,1H),8.76(s,2H),8.16(dd,J=8.1,0.8Hz,1H),8.02(dd,J=8.2,2.3Hz,1H),7.60-7.56(m,2H),7.53-7.49(m,2H),4.59(s,2H);ESIMS m/z 310[M+H]+,m/z 308([M-H]-)。
步骤D:制备2-(5-(4-氯苯基)吡啶-2-基)-1-(嘧啶-5-基)丙-2-醇(25)。
在N2气氛下向1-(5-(4-氯苯基)吡啶-2-基)-2-(嘧啶-5-基)乙酮(50mg,0.161mmol)在THF(1614μL)的冷却至-78℃的磁力搅拌的混合物中逐滴添加MeMgBr在Et2O中的溶液(3.0M,108μL,0.323mmol)。将反应混合物在-78℃搅拌105min,通过逐滴添加NH4Cl饱和水溶液(2mL)使其淬灭。将反应混合物从冷却浴中取出,升温至室温,用水稀释,并用EtOAc(3x)萃取。通过使合并的有机萃取物穿过相分离器滤芯来使其干燥,将挥发性组分在温和的N2流下蒸发。使所得残余物吸附到层上,并通过柱色谱纯化(SiO2,50→80%EtOAc在己烷中),得到回收的起始原料(42%)和作为淡黄色固体的标题化合物(19mg,36.1%):参见表2的表征数据。
步骤C和D可以按任一顺序进行,以获得所需产物。
实施例7:制备3,3-二甲基-1-(1H-四唑-1-基)-2-[5-[4-(三氟-甲氧基)苯基]吡啶-2-基]丁-2-醇(26)。
步骤A:制备2-溴-5-(4-(三氟甲氧基)苯基)吡啶。
向装备有磁力搅拌棒的微波小瓶中添加(6-溴吡啶-3-基)硼酸(1.37g,6.77mmol)、1-碘-4-(三氟甲氧基)苯(1.5g,5.21mmol)和DMF(11.9mL),然后添加K2CO3(2.52g,18.2mmol)和水(2.98mL)。将反应混合物在N2下搅拌5min并用Pd(PPh3)4(16.05mg,0.014mmol)处理。将反应容器封上盖子,将其在Biotage Initiator微波反应器中在120℃放置1h,所述微波反应器具有从容器侧面进行监测的外部IR-传感器温度。在用EtOAc(100mL)冲洗下使冷却的反应混合物过滤通过层,将滤液先后用NaHCO3饱和水溶液(50mL)、水(3x 50mL)、和盐水洗涤(50mL)。将有机相用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→10%EtOAc在己烷中),得到作为灰白色固体的标题化合物(1.07g,63%):IR(薄膜)3036,1453,1210,1167cm-1;1H NMR(400MHz,CDCl3)δ8.57(dd,J=2.6,0.8Hz,1H),7.71(dd,J=8.2,2.6Hz,1H),7.63-7.54(m,3H),7.38-7.29(m,2H);19F NMR(376MHz,CDCl3)δ-57.83;HRMS-ESI(m/z)[M+H]+,对于C12H8BrF3NO,计算值为317.9736;实测值为317.9735。
步骤B:制备2,2-二甲基-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-1-醇。
在-78℃向2-溴-5-(4-(三氟甲氧基)苯基)吡啶(2g,6.32mmol)和特戊醛(2mL,12.5mmol)在甲苯(20mL)的溶液中添加n-BuLi(10mL,15.8mmol),将混合物在相同温度搅拌1h。将反应混合物用NH4Cl饱和水溶液淬灭,升温至室温,并用EtOAc萃取。将有机萃取物用盐水洗涤,用Na2SO4干燥,并减压浓缩。将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为黄色油状物的标题化合物(3g,60%,通过LCMS得到的纯度)。化合物无需进一步纯化即可用于下一步骤。
步骤C:制备2,2-二甲基-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-1-酮。
在0℃向2,2-二甲基-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-1-醇(3g,5.6mmol,60%纯度)在无水CH2Cl2(30mL)的溶液中按份添加戴斯-马丁高碘烷(7.8g,18.4mmol),将反应混合物在室温搅拌2h。将反应混合物真空过滤,用CH2Cl2洗涤,将滤液减压浓缩。将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为灰白色固体的标题化合物(500mg,25%,历经2步)。
步骤D:制备2-(2-叔丁基环氧乙-2-基)-5-(4-(三氟甲氧基)苯基)吡啶。
向三甲基碘化亚砜(613mg,2.78mmol)在THF(5mL)的悬浮液中添加在0℃的NaH(110mg,2.78mmol,60%在矿物油中的分散体),然后添加DMSO(1mL),将反应混合物在0℃搅拌1h,然后用2,2-二甲基-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-1-酮(600mg,1.85mmol)在THF中的溶液进行处理。将反应混合物升温至室温,搅拌15h,倒入冰水中,并用EtOAc萃取。将有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩。将残余物通过柱色谱纯化(SiO2,15→20%EtOAc在石油醚中),得到作为黄色油状物的标题化合物(150mg,24%)。
步骤E:制备3,3-二甲基-1-(1H-四唑-1-基)-2-[5-[4-(三氟甲氧基)苯基]吡啶-2-基]丁-2-醇(26)。
在惰性气氛下向2-(2-叔丁基环氧乙-2-基)-5-(4-(三氟甲氧基)苯基)吡啶(450mg,1.33mmol)在DMSO(5mL)的溶液中添加1H-四唑(187mg,2.67mmol)和K2CO3(276mg,2.0mmol)。将反应混合物加热至并在70℃搅拌48h,冷却至室温,倒入水中,并用EtOAc萃取。将有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩。将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为灰白色固体的标题化合物(80mg,15%):参见表2的表征数据。
2H区域异构体也分离(18mg,3%)为灰白色固体:1H NMR(400MHz,CDCl3):δ8.61(d,J=2.4Hz,1H),8.26(s,1H),7.84(dd,J=8.3,2.4Hz,1H),7.70(d,J=8.3Hz,1H),7.57(d,J=8.4Hz,2H),7.31(d,J=8.4Hz,2H),5.70(d,J=13.4Hz,1H),5.31(brs,1H),5.09(d,J=13.6Hz,1H),1.09(s,9H);ESIMS m/z 408[M+H]+。
实施例8:制备2,2-二甲基-1-(嘧啶-5-基)-1-(5-(4-(三氟-甲氧基)苯基)吡啶-2-基)丙-1-醇(27)。
步骤A:制备嘧啶-5-基(5-(4-(三氟甲氧基)苯基)吡啶-2-基)甲酮。
标题化合物由2-溴-5-(4-(三氟甲氧基)苯基)-吡啶和N-甲氧基-N-甲基嘧啶-5-甲酰胺使用实施例3A中所述的条件制备。需要通过反相柱色谱进行另外的纯化(C18,10→100%CH3CN在水中),得到收率为31%的作为灰白色固体的标题化合物:IR(薄膜)1663,1316,1163cm-1;1H NMR(400MHz,CDCl3)δ9.56(s,2H),9.40(s,1H),8.96(dd,J=2.3,0.8Hz,1H),8.33(dd,J=8.2,0.8Hz,1H),8.13(dd,J=8.2,2.3Hz,1H),7.73-7.67(m,2H),7.40(m,2H);19F NMR(376MHz,CDCl3)δ-57.77;HRMS-ESI(m/z)[M+H]+,对于C17H11F3N3O2,计算值为346.0798;实测值为346.0803。
步骤B:制备2,2-二甲基-1-(吡啶-3-基)-1-(5-(4-(三氟甲氧基)-苯基)吡啶-2-基)丙-1-醇(27)。
向装备有磁力搅拌棒的小瓶中添加ZnCl2(14.3mg,0.105mmol)和LiCl(16.3mg,0.384mmol),将液面上空间用N2吹洗。在室温添加1MtBuMgCl(593μL,0.593mmol)在THF中的溶液,将反应混合物搅拌1h,冷却至0℃,并用嘧啶-5-基(5-(4-(三氟甲氧基)苯基)吡啶-2-基)甲酮(114mg,0.33mmol)在无水THF(2327μL)中的溶液处理。在0℃保持1h之后,添加另外的tBuMgCl溶液(350μL,0.350mmol),继续在0℃搅拌另外1h,在其还冷时用NH4Cl饱和水溶液(2mL)淬灭。将混合物用EtOAc(3x 2mL)萃取,将合并的萃取物用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→45%EtOAc在己烷中),得到作为亮黄色半固体的标题化合物(47.9mg,36%):参见表2的表征数据。
实施例9:制备1-(4-氯-2-氟苯基)-3-(1H-四唑-1-基)-2-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-2-醇(28)。
步骤A:制备5-(4-(三氟甲氧基)苯基)吡啶甲醛。
在-78℃向2-溴-5-(4-(三氟甲氧基)苯基)吡啶(5.00g,15.8mmol)在甲苯(50mL)的溶液中逐滴添加n-BuLi(2.5M在己烷中,16mL,39.5mmol),将反应混合物搅拌15min,用无水DMF(6mL,79.1mmol)逐滴进行处理,并在-78℃搅拌1h。将反应混合物用NH4Cl饱和水溶液淬灭,升温至室温,并用EtOAc萃取。将萃取物用Na2SO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为黄色固体的标题化合物(1.2g,29%)。
步骤B:制备2-(4-氯-2-氟苯基)-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)乙醇。
向Mg粉(291mg,11.2mmol)在无水Et2O(20mL)的悬浮液中缓慢添加1-(溴甲基)-4-氯-2-氟苯(2.5g,11.2mmol),将反应混合物剧烈搅拌15min(观察到剧烈回流)。在0℃将该格氏试剂溶液逐滴添加到5-(4-(三氟甲氧基)苯基)吡啶甲醛(1.2g,4.5mmol)在Et2O(10mL)的溶液中,将反应混合物升温至室温并搅拌1h。将反应混合物用冰水(100mL)淬灭,并用EtOAc萃取。将萃取物用Na2SO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为灰白色固体的标题化合物(1.1g,59%)。
步骤C:制备2-(4-氯-2-氟苯基)-1-(5-(4-(三氟甲氧基)苯基)-吡啶-2-基)乙酮。
在0℃向2-(4-氯-2-氟苯基)-1-(5-(4-(三氟甲氧基)苯基)-吡啶-2-基)乙醇(1.1g,2.67mmol)在无水CH2Cl2(20mL)的溶液中按份添加戴斯-马丁高碘烷(2.3g,5.35mmol),将反应混合物升温至室温并搅拌16h。将反应混合物真空过滤,将滤饼用CH2Cl2洗涤,将滤液减压浓缩。将残余物通过柱色谱纯化(SiO2,10→15%EtOAc在石油醚中),得到作为灰白色固体的标题化合物(900mg,83%)。
步骤D:制备2-(2-(4-氯-2-氟苄基)环氧乙-2-基)-5-(4-(三氟-甲氧基)苯基)吡啶。
在50℃向三甲基碘化亚砜(320mg,1.45mmol)在tBuOH(5mL)的悬浮液中添加叔丁醇钾(KOtBu,163mg,1.45mmol),将反应混合物搅拌30min,用2-(4-氯-2-氟苯基)-1-(5-(4-(三氟甲氧基)-苯基)吡啶-2-基)乙酮(400mg,0.96mmol)在tBuOH(2mL)中的溶液处理,并在50℃搅拌16h。将反应混合物冷却至室温,倒入冰水中,并用EtOAc萃取。将有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,减压浓缩,将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为黄色油状物的标题化合物(140mg,24%)。
步骤E:制备1-(4-氯-2-氟苯基)-3-(1H-四唑-1-基)-2-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-2-醇(28)。
在惰性气氛下向2-(2-(4-氯-2-氟苄基)环氧乙-2-基)-5-(4-(三氟甲氧基)-苯基)吡啶(130mg,0.3mmol)在DMSO(5mL)的溶液中添加1H-四唑(43mg,0.6mmol)和K2CO3(63mg,0.45mmol)。将反应混合物加热至70℃并搅拌30h。将反应混合物冷却至室温,倒入水中,并用EtOAc萃取。将有机萃取物用盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩。将残余物通过柱色谱纯化(SiO2,5→10%EtOAc在石油醚中),得到作为灰白色固体的标题化合物(23mg,15%):参见表2的表征数据。
2H区域异构体(30mg,20%)也作为灰白色固体获得:1H NMR(300MHz,CDCl3):δ8.63(d,J=2.2Hz,1H),8.40(s,1H),7.84(dd,J=8.2,2.3Hz,1H),7.58(d,J=8.4Hz,2H),7.48(d,J=8.2Hz,1H),7.32(d,J=8.4Hz,2H),7.16(t,J=8.2Hz,1H),7.04-6.92(m,2H),5.32(d,J=13.8Hz,1H),5.10(s,1H),5.06(d,J=13.8Hz,1H),3.35(d,J=13.8Hz,1H),3.26(d,J=13.8Hz,1H);ESIMS m/z 494[M+H]+。
实施例10:制备1-(5-(4-氯苯氧基)吡啶-2-基)-4,4-二甲基-1-(嘧啶-5-基)戊-2-炔-1-醇(29)和1-(5-(4-氯苯氧基)吡啶-2-基)-1-(嘧啶-5-基)丙-1-醇(30)。
向装备有磁力搅拌棒的小瓶中添加3,3-二甲基丁-1-炔(23.7μL,0.289mmol),将小瓶用N2吹洗。添加无水THF(0.2mL),将反应混合物冷却至0℃。将所得溶液用EtMgBr(1.0M,289μL,0.289mmol)在THF中的溶液逐滴进行处理,将混合物在0℃搅拌15min,升温至40℃并在40℃搅拌2h,然后冷却至室温。向单独的小瓶中添加(5-(4-氯苯氧基)吡啶-2-基)(嘧啶-5-基)甲酮(30mg,0.096mmol)和THF(481μL),将混合物冷却至0℃。逐滴添加新鲜制备的乙炔化物,将反应在0℃搅拌4h。将反应在其还冷时用NH4Cl饱和水溶液(2mL)淬灭,用EtOAc(3x 2mL)萃取,将合并的萃取物用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→60%EtOAc在己烷中),得到标题化合物29和30。
化合物29(17mg,45%收率)分离为淡黄色的混浊的粘性油状物:参见表2的表征数据。
化合物30(3.6mg,11%收率)分离为淡黄色的粘性油状物:参见表2的表征数据。
实施例11:制备2-(4-氯-2-氟苯基)-1-(5-(4-氯苯氧基)-吡啶-2-基)-1-(嘧啶-5-基)乙醇(41)。
向Mg粉(0.012g,0.48mmol)在Et2O(2mL)的搅拌悬浮液中缓慢添加1-(溴甲基)-4-氯-2-氟苯(0.076g,0.48mmol),在这一过程中观察到溶剂回流。在添加完全治好,将反应混合物在室温搅拌30min,在0℃将新鲜制备的格氏试剂添加到(5-(4-氯苯氧基)吡啶-2-基)(嘧啶-5-基)甲酮(得自实施例3,在3B中使用4-氯苯酚;0.1g,0.32mmol)在Et2O(3mL)的溶液中。将反应混合物升温至室温,搅拌30min,小心用NH4Cl饱和水溶液淬灭,并用EtOAc(2x20mL)萃取。将合并的有机萃取物用Na2SO4干燥,过滤,减压浓缩,将残余物通过柱色谱纯化(SiO2),得到作为黄色液体的标题化合物(10mg,7%):参见表2的表征数据。
实施例12:制备1-(4-氯-2-氟苯基)-2-(5-(4-氯苯氧基)-吡啶-2-基)-3-(1H-四唑-1-基)丙-2-醇(42)。
步骤A:制备5-(4-氯苯氧基)吡啶甲腈。
向装备有磁力搅拌棒的烘箱干燥的圆底烧瓶中添加2-氰基-5-氟吡啶(10g,81.9mmol)、4-氯苯酚(15.7g,122.9mmol)、和K2CO3(22.1g,163.8mmol),然后添加DMSO(100mL)。将反应混合物加热至120℃并在120℃搅拌3h。将反应冷却至室温,用水(200mL)稀释,通过过滤(Buchner漏斗)收集所得固体,将其风干,用戊烷洗涤,得到5-(4-氯苯氧基)吡啶甲腈和5-(4-氯苯氧基)吡啶甲酰胺的混合物。使固体(10g)溶解于THF,将所得溶液用三乙胺(Et3N,8.14g,80.6mmol)处理,冷却至0℃,并历时30min的时间段用三氟乙酸酐(TFAA,16.9g,80.6mmol)逐滴进行处理。将反应混合物搅拌10min,用水(100mL)淬灭,并用EtOAc(500mL)萃取。将有机萃取物用水和盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩。将残余物通过柱色谱纯化(SiO2),得到标题化合物(7g,48%)。
步骤B:制备5-(4-氯苯氧基)吡啶甲醛。
向5-(4-氯苯氧基)吡啶甲腈(7g,30.4mmol)在THF(70mL)的-78℃的溶液中添加DIBAL-H(25%在甲苯中,86.4mL,152mmol),将反应混合物在-78℃搅拌30min。将反应混合物用2N HCl在-78℃淬灭,升温至室温,并用EtOAc萃取。将有机萃取物用水和盐水洗涤,用Na2SO4干燥,过滤,并减压浓缩。将残余物通过柱色谱纯化(SiO2),得到标题化合物(5.4g,76%)。
步骤C:制备2-(4-氯-2-氟苯基)-1-(5-(4-氯苯氧基)吡啶-2-基)乙醇。
向Mg粉(1.12g,46.9mmol)在Et2O(60mL)的搅拌悬浮液中缓慢添加1-(溴甲基)-4-氯-2-氟苯(0.615g,5.08mmol),在这一过程中观察到溶剂回流。在添加完全之后,将反应混合物在室温搅拌30min。在0℃将新鲜制备的格氏试剂添加到5-(4-氯苯氧基)吡啶甲醛(5.4g,23.4mmol)在Et2O(60mL)的溶液中,将混合物升温至室温,搅拌30min,用NH4Cl饱和水溶液淬灭,并用EtOAc(2x 200mL)萃取。将合并的有机萃取物用Na2SO4干燥,过滤,并减压浓缩,得到残余物,将其通过柱色谱纯化(SiO2),得到作为白色固体的标题化合物(4g,45%)。
步骤D:制备2-(4-氯-2-氟苯基)-1-(5-(4-氯苯氧基)吡啶-2-基)乙酮。
向2-(4-氯-2-氟苯基)-1-(5-(4-氯苯氧基)-吡啶-2-基)乙醇(4.00g,10.6mmol)在CH2Cl2(40mL)的0℃溶液中按份添加戴斯-马丁高碘烷(8.99g,21.2mmol),将反应混合物在室温搅拌16h。在用CH2Cl2冲洗下使反应混合物过滤通过将滤液减压浓缩。将残余物通过柱色谱纯化(SiO2),得到标题化合物(3.6g,92%)。
步骤E:制备2-(2-(4-氯-2-氟苄基)环氧乙-2-基)-5-(4-氯苯氧基)吡啶。
在0℃向2-(4-氯-2-氟苯基)-1-(5-(4-氯苯氧基)吡啶-2-基)乙酮(1g,2.66mmol)在Et2O(10mL)的搅拌悬浮液中缓慢添加重氮甲烷(50mL,0.5M在Et2O中),将混合物在室温搅拌16h。小心用冰冷的水将反应混合物淬灭,并将其用EtOAc萃取。将有机萃取物用Na2SO4干燥,过滤,并减压浓缩,得到油性残余物,将其通过柱色谱纯化(SiO2),得到标题化合物(0.350g,36%)。
步骤F:制备1-(4-氯-2-氟苯基)-2-(5-(4-氯苯氧基)吡啶-2-基)-3-(1H-四唑-1-基)丙-2-醇(42)。
在室温在惰性气氛(N2)下向2-(2-(4-氯-2-氟苄基)-环氧乙-2-基)-5-(4-氯苯氧基)吡啶(0.350g,8.99mmol)在DMSO(3.5mL)的搅拌溶液中添加1H-四唑(0.125g,17.98mmol),然后添加K2CO3(0.186g,13.485mmol)。将反应混合物升温至60℃并在60℃搅拌16h。将反应混合物冷却至室温,用冰冷的水(20mL)稀释,并用EtOAc(2x 100mL)萃取。将合并的有机萃取物用无水Na2SO4干燥,过滤,减压浓缩,将残余物通过柱色谱纯化(SiO2),得到作为灰白色固体的标题化合物(140mg,34%):参见表2的表征数据。
实施例13:制备2-环丙基-1-(嘧啶-5-基)-1-(5-(4-(三氟甲氧基)苯氧基)吡啶-2-基)乙醇(45)。
向装备有磁力搅拌棒的小瓶中添加5-溴嘧啶(33.9mg,0.213mmol)和2-环丙基-1-(5-(4-(三氟甲氧基)苯氧基)吡啶-2-基)乙酮(由2-环丙基-N-甲氧基-N-甲基乙酰胺使用实施例3,步骤A和B中所述的条件制备;40mg,0.119mmol),然后添加THF(593μL),将反应混合物冷却至-78℃,并用2.5Mn-BuLi(95μL,0.237mmol)在己烷中的溶液进行处理。将反应混合物在-78℃搅拌2h,用0.5mL的1M HCl淬灭,将其在水(2mL)和EtOAc(2mL)之间分配。使各相分离,将水相进一步用EtOAc(2x 2mL)萃取。将合并的有机物用盐水(5mL)洗涤,用Na2SO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→100%EtOAc在己烷中),得到作为淡黄色的粘性油状物的标题化合物(4.1mg,8%):参见表2的表征数据。
实施例14:2-(5-(4-氯苯基)吡啶-2-基)-1,1,1-三氟-3-(嘧啶-5-基)丙-2-醇(46)。
在0℃向1-(5-(4-氯苯基)吡啶-2-基)-2-(嘧啶-5-基)乙酮(50mg,0.161mmol)和三甲基(三氟甲基)硅烷(35.8μL,0.242mmol)在THF(807μL)的磁力搅拌的混合物中添加CsF(4.90mg,0.032mmol),将反应混合物搅拌85min,用2mL的1N HCl淬灭,搅拌45min,升温至室温,用水稀释,并用EtOAc萃取(3x)。通过使合并的有机萃取物穿过相分离器滤芯将其干燥。将溶剂蒸发,将所得残余物通过柱色谱纯化(SiO2,30→60%丙酮在己烷中),得到标题化合物及其对应的TMS醚。将TMS醚溶解于THF(1.5mL),用另外的1N HCl(1mL)处理,并在室温搅拌过夜,此时的LCMS显示完全转化为游离羟基产物。通过添加NaHCO3饱和水溶液将反应混合物淬灭(观察到形成气体),用EtOAc(3x)萃取,通过使合并的有机萃取物穿过相分离器滤芯将其干燥。在温和的N2流下移除挥发性组分,得到作为棕色油状物的标题化合物(28mg,45.7%):参见表2的表征数据。
实施例15:制备(2,4-二氟苯基)(嘧啶-5-基)(5-(4-(三氟-甲氧基)苯基)吡啶-2-基)甲醇(91)。
向装备有磁力搅拌棒的小瓶中添加1-溴-2,4-二氟苯(19.9μL,0.176mmol),将小瓶用N2吹洗。添加无水Et2O(306μL),将反应混合物冷却至-78℃并用n-BuLi在己烷中的溶液(2.5M,70.4μL,0.176mmol)处理。将反应混合物在-78℃搅拌30min并用嘧啶-5-基(5-(4-(三氟甲氧基)苯基)-吡啶-2-基)甲酮(实施例8A;52.8mg,0.153mmol)在无水Et2O(306μL)中的溶液进行逐滴处理,用另外的Et2O(0.5mL)和THF(1mL)冲洗。将所得混合物在-78℃搅拌2h,升温至0℃并在0℃搅拌1h,然后在其还冷时用NH4Cl饱和水溶液(2mL)淬灭。将混合物用EtOAc(3x 2mL)萃取,将合并的萃取物用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→40%EtOAc在己烷中),得到作为灰白色粘性半固体的标题化合物(27mg,37%):参见表2的表征数据。
实施例16:制备2,2-二甲基-1-嘧啶-5-基-1-[5-[4-(三氟甲氧基)苯基]-2-吡啶基]丁-1-醇(93)。
步骤A:制备(5-溴吡啶-2-基)(嘧啶-5-基)甲酮。
向装备有磁力搅拌棒的圆底烧瓶中装入5-溴-2-碘吡啶(7.13g,25.1mmol),将烧瓶用N2吹洗。添加无水THF(67mL),将反应混合物冷却至-40℃,用2.0M异丙基氯化镁在THF中的溶液(12.56mL,25.1mmol)历时10min的时间段进行处理,并在-40℃搅拌1h。将所得混浊的亮棕色反应混合物用N-甲氧基-N-甲基嘧啶-5-甲酰胺(4.2g,25.1mmol)在无水THF(16.8mL)中的溶液历时10min的时间段进行处理,将其在-40℃搅拌45min,并升温至室温。将反应混合物用饱和(sat’d)水性(aq)氯化铵(NH4Cl)溶液(100mL)淬灭,并用DCM(3x50mL)萃取。将合并的有机相用Na2SO4干燥,过滤,浓缩,将残余物通过柱色谱纯化(SiO2,0→20%EtOAc在DCM中),得到作为亮黄色固体的标题化合物(3.41g,50%):IR(薄膜)1667,1560,1314cm-1;1H NMR(400MHz,CDCl3)δ9.50(s,2H),9.39(s,1H),8.81(dd,J=2.0,1.0Hz,1H),8.18-8.06(m,2H);HRMS-ESI(m/z)[M+H]+,对于C10H7BrN3O,计算值为263.9767;实测值为263.9767。
步骤B:制备1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丁-1-醇。
将装备有磁力搅拌棒并配有隔膜帽的小瓶用N2吹洗并装入(5-溴吡啶-2-基)(嘧啶-5-基)甲酮(210mg,0.80mmol)和无水THF(2.6mL)。将反应混合物冷却至0℃,用1M叔戊基氯化镁在Et2O中的溶液(1.19mL,1.193mmol)逐滴进行处理,将其在0℃搅拌直至反应完全,并用NH4Cl饱和水溶液(5mL)淬灭。将反应混合物升温至室温,用EtOAc(3x 5mL)萃取,将合并的有机萃取物用MgSO4干燥,过滤,浓缩,并通过柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为淡褐色固体的标题化合物(134mg,49%):IR(薄膜)3233,1556,1459,1412,1362cm-1;1H NMR(400MHz,CDCl3)δ9.18(s,2H),9.07(s,1H),8.64(dd,J=2.4,0.8Hz,1H),7.88(dd,J=8.6,2.4Hz,1H),7.67(dd,J=8.6,0.8Hz,1H),5.42(s,1H),1.54-1.40(m,1H),1.39-1.28(m,1H),0.99(s,6H),0.80(t,J=7.5Hz,3H);HRMS-ESI(m/z)[M+H]+,对于C15H19BrN3O,计算值为336.0706;实测值为336.0708。
步骤C:制备2,2-二甲基-1-(嘧啶-5-基)-1-(5-(4-(三氟甲氧基)-苯基)吡啶-2-基)丁-1-醇。
标题化合物由1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丁-1-醇和(4-(三氟甲氧基)苯基)硼酸根据实施例7A中所述的条件制备并以70%收率分离为淡黄色泡沫状物:参见表2的表征数据。
实施例17:制备1-(5-(2-氟-4-(三氟甲氧基)苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(124)。
步骤A:制备2-(2-氟-4-(三氟甲氧基)苯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环。
向装备有磁力搅拌棒的微波小瓶中添加4,4,4',4',5,5,5',5'-八甲基-2,2'-二(1,3,2-二氧硼戊环)(294mg,1.16mmol)、乙酸钾(KOAc;189mg,1.93mmol)和Pd(dppf)Cl2(70.6mg,0.097mmol),将小瓶用N2吹洗。将所得混合物用1-溴-2-氟-4-(三氟甲氧基)苯(250mg,0.96mmol)在1,4-二氧杂环己烷(3.9mL)中的溶液处理。将反应容器封上盖子,将其在Biotage Initiator微波反应器中在100℃放置2h,所述微波反应器具有从容器侧面进行监测的外部IR-传感器温度。在用EtOAc冲洗下使冷却的反应混合物过滤通过层,将滤液用NaHCO3饱和水溶液(15mL)和盐水(2x 15mL)洗涤。将有机相用MgSO4干燥,过滤,并浓缩成棕色油状物,其无需进一步纯化即可使用:1H NMR(400MHz,CDCl3)δ7.77(dd,J=8.3,6.8Hz,1H),7.01(ddd,J=8.3,2.3,1.1Hz,1H),6.92(ddd,J=9.6,2.2,1.0Hz,1H),1.36(s,12H);EIMS m/z 306。
步骤B:制备1-(5-(2-氟-4-(三氟甲氧基)苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇。
标题化合物由1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(按照实施例16A-16B中所述用tBuMgCl在-78℃制备)和2-(2-氟-4-(三氟甲氧基)苯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环根据实施例7A中所述的条件制备并以47%收率分离为白色泡沫状物:参见表2的表征数据。
实施例18:制备1-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)乙酮O-甲基肟(130和132)。
在室温向装备有磁力搅拌棒的小瓶中添加按照实施例16中所述制备的1-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)乙酮(188mg,0.520mmol)、NaOAc(51.2mg,0.624mmol)、O-甲基羟胺盐酸盐(52.1mg,0.624mmol)和MeOH(3.5mL)将反应混合物在室温搅拌约15h。将反应混合物用NaHCO3饱和水溶液(10mL)稀释,用DCM(3x 5mL)萃取,将合并的有机萃取物用水(2x 5mL)洗涤,用Na2SO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→40%EtOAc在己烷中),得到作为白色固体的(E)-1-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)乙酮O-甲基肟(154mg,76%)和作为白色固体的(Z)-1-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)乙酮O-甲基肟(14mg,7%):参见表2的表征数据。
实施例19:制备5-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)噻吩-2-甲酰胺(133)。
标题化合物由1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇和5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩-2-甲腈根据实施例7A中所述的条件制备并以10%收率分离为白色固体:参见表2的表征数据。
实施例20:制备2-(3-氟苯基)-1-嘧啶-5-基-1-[5-[4-(三氟甲氧基)-苯基]-2-吡啶基]乙醇(139)。
步骤A:制备1-(5-溴吡啶-2-基)-2-(3-氟苯基)-1-(嘧啶-5-基)乙醇。
向装备有磁力搅拌棒的烘箱干燥的小瓶中添加已经用2N HCl洗涤并干燥的镁金属(Mg)(18.0mg,0.74mmol),将小瓶用N2吹洗。添加I2晶体,将混合物用无水Et2O(1.4mL)稀释并用1-(溴甲基)-3-氟苯(91μL,0.74mmol)以使得不会观察从Mg冒泡的速率进行处理。定期将反应容器升温,以保证温和回流,直到I2颜色消失且大多数的Mg已消耗。将反应混合物冷却至室温并剧烈搅拌30。向单独的小瓶中添加(5-溴吡啶-2-基)(嘧啶-5-基)甲酮(150mg,0.57mmol)和无水THF(2.8mL)。将所得溶液冷却至0℃,将新鲜制备的格氏试剂溶液缓慢转移至包含酮的烧瓶中,用另外的无水THF(1.4mL)冲洗。将混合物在0℃搅拌3h,当冰融化时使其升温至室温。在5h之后,将反应混合物用NH4Cl饱和水溶液(sat’d aq)(5mL)淬灭,并用EtOAc(3x 3mL)萃取。将合并的萃取物用MgSO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→60%EtOAc在己烷中),得到作为淡黄色粘性油状物的标题化合物(112mg,52%):1H NMR(400MHz,CDCl3)δ9.11(s,1H),8.95(s,2H),8.59(dd,J=2.3,0.8Hz,1H),7.84(dd,J=8.4,2.3Hz,1H),7.38(dd,J=8.4,0.8Hz,1H),7.20-7.08(m,1H),6.89(tdd,J=8.4,2.6,1.0Hz,1H),6.82-6.72(m,2H),4.67(s,1H),3.75(d,J=13.6Hz,1H),3.50(d,J=13.6Hz,1H);19F NMR(376MHz,CDCl3)δ-112.95;IR(薄膜)3217,1411,1092,1007,725cm-1;HRMS-ESI(m/z)[M+H]+,对于C17H14BrFN3O,计算值为374.0299;实测值为374.0299。
步骤B:制备2-(3-氟苯基)-1-(嘧啶-5-基)-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)乙醇。
标题化合物由1-(5-溴吡啶-2-基)-2-(3-氟苯基)-1-(嘧啶-5-基)乙醇和(4-(三氟甲氧基)苯基)硼酸根据实施例7A中所述的条件制备并以64%收率分离为淡黄色的粘性半固体:参见表2的表征数据。
实施例21:制备1-(5-(4-(1,1-二氟乙基)苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(155)。
步骤A:制备1-溴-4-(1,1-二氟乙基)苯。
在室温在N2下向装备有磁力搅拌棒的小瓶中添加1-(4-溴苯基)乙酮(295mg,1.48mmol)在无水DCM(3.0mL)中的溶液,然后添加50%在甲苯中的溶液(1.6mL,4.45mmol),将小瓶密封。将反应混合物在室温搅拌约15h,但是几乎没有发生转化。将混合物浓缩,用另外的溶液(0.66mL,1.79mmol)处理,将其升温至85℃并在85℃在N2下搅拌5h。将反应混合物冷却至0℃,通过逐滴添加NaHCO3饱和水溶液直到停止形成气体将其小心淬灭。将两相混合物用DCM(2x 5mL)萃取,将合并的萃取物用Na2SO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为透明液体的标题化合物(83mg,25%):1H NMR(400MHz,CDCl3)δ7.58-7.53(m,2H),7.41-7.35(m,2H),1.90(t,J=18.1Hz,3H);19F NMR(376MHz,CDCl3)δ-87.86;IR(薄膜)1599,1294,1089cm-1;EIMS m/z 220/221。
步骤B:制备2-(4-(1,1-二氟乙基)苯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环。
标题化合物由1-溴-4-(1,1-二氟乙基)苯根据实施例17A中所述的条件制备,分离为棕色油状物,其无需进一步纯化即可使用:1H NMR(400MHz,CDCl3)δ7.91-7.83(m,2H),7.55-7.45(m,2H),1.91(t,J=18.2Hz,3H),1.35(s,12H);19F NMR(376MHz,CDCl3)δ-88.45;EIMS m/z 268。
步骤C:制备1-(5-(4-(1,1-二氟乙基)苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇。
标题化合物由1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇和2-(4-(1,1-二氟乙基)苯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环根据实施例7A中所述的条件制备并以65%收率分离为淡棕色固体:参见表2的表征数据。
实施例22:制备1-(5-(4-碘苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(165)。
向装备有磁力搅拌棒的小瓶中添加2,2-二甲基-1-(嘧啶-5-基)-1-(5-(4-(三甲基甲硅烷基)苯基)吡啶-2-基)丙-1-醇(59mg,0.15mmol)在DCM(753μL)中的溶液,然后添加ICl(48.9mg,0.301mmol)在DCM(0.5mL)中的溶液,将反应混合物在室温搅拌。在约23h之后,将混合物用另外的ICl(48.9mg,0.301mmol)在DCM(0.5mL)中的溶液进行处理,将其搅拌4h,并用硫代硫酸钠饱和水溶液(Na2S2O3;2mL)淬灭。将混合物用DCM(2mL)稀释,使各相分离。将有机相用水(3x 2mL)洗涤,用Na2SO4干燥,过滤,并浓缩。将残余物通过柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为灰白色固体的标题化合物(32mg,47%):参见表2的表征数据。
实施例23:制备5-(1-甲氧基-2,2-二甲基-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙基)嘧啶(277)
向装备有磁力搅拌棒的小瓶中添加2,2-二甲基-1-(嘧啶-5-基)-11-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丙-1-醇(27)(150mg,0.372mmol)和干燥THF(2479μl),将液面上空间用N2吹洗。向其中添加氢化钠(29.7mg,0.744mmol)。将反应混合物在0℃搅拌5min,此时经注射器添加碘甲烷(58.1μl,0.930mmol)。将反应逐步升温至室温,然后在16h之后通过添加1.5mL的NH4Cl饱和水溶液将其淬灭。将反应混合物用水稀释,并用EtOAc萃取3次。通过使合并的有机层穿过相分离器来将其干燥,在N2下移除挥发物。将残余物通过柱色谱纯化(SiO2,0→25%EtOAc在己烷中),得到作为油性黄色固体的标题化合物(128mg,82%):参见表2的表征数据。
实施例24:制备1-(5-(4-碘苯基)吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(156)。
步骤A:制备2-(4-溴-3-甲基苯基)-2-甲基丙腈
在氩气气氛下在干燥100mL圆底烧瓶中,向2-(4-溴-3-甲基苯基)乙腈(1g,4.76mmol)在干燥THF(9.52ml)在冰浴温度的磁力搅拌的混合物中添加NaH(0.571g,14.28mmol)。将反应混合物在冰浴温度搅拌1h,然后逐滴添加碘甲烷(0.893ml,14.28mmol),继续搅拌3h。将反应混合物倒入碎冰和水中,并用乙酸乙酯萃取(3x)。将合并的有机萃取物用硫酸钠干燥,过滤,并蒸发,得到1.1g(92%)作为棕色油状物的标题化合物,其无需进一步纯化即可使用。1H NMR(400MHz,CDCl3)δ7.53(d,J=8.4Hz,1H),7.34(d,J=2.4Hz,1H),7.13(dd,J=8.3,2.5Hz,1H),2.43(s,3H),1.70(s,6H)。GCMS m/z 237。
步骤B:制备5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)嘧啶。
在装备有冷凝器、搅拌棒、温度探针、和氮气入口的4-颈500mL烧瓶中,将1-(5-溴吡啶-2-基)-2,2-二甲基-1-(嘧啶-5-基)丙-1-醇(9.74g,28.7mmol)在二氧杂环己烷(115ml)中搅拌。添加乙酸钾(3.70g,37.3mmol)和4,4,4',4',5,5,5',5'-八甲基-2,2'-二(1,3,2-二氧硼戊环)(9.58g,37.3mmol)。将混合物用氮气喷射5分钟。添加Pd(dppf)Cl2(1.070g,1.436mmol)。将混合物加热至85℃并保持2h,然后使其冷却。将反应混合物用DCM(100mL)稀释,并使其过滤通过Celite。将滤液浓缩至干燥,得到胶粘的固体。将固体在MTBE(30mL)和庚烷(100mL)中制成浆液。收集固体,将其用庚烷洗涤,并在35℃真空干燥,得到13.6g(86%)作为灰色固体的标题化合物,其无需进一步纯化即可原样使用。1H NMR(500MHz,CDCl3)δ9.11(s,2H),9.05(s,1H),8.90(s,1H),8.45(dd,J=8.1,1.4Hz,1H),8.06(d,J=8.1Hz,1H),1.43-1.23(m,24H),1.02(s,9H)。
步骤C:制备2-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)-3-甲基苯基)-2-甲基丙腈
在N2气氛下在干燥的5mL微波小瓶中,向5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)嘧啶(400mg,0.808mmol)在甲苯(2.423mL)的磁力搅拌的混合物中添加2-(4-溴-3-甲基苯基)-2-甲基丙腈(385mg,1.615mmol)、氟化铯(368mg,2.423mmol)、和四(三苯基膦)钯(0)(140mg,0.121mmol)。添加乙醇(0.808mL)和水(0.808mL),将反应混合物用氩气吹洗1分钟,然后将其在Biotage Initiator微波器中在110℃搅拌30分钟。将反应混合物冷却至RT,用DCM和NH4Cl饱和水溶液稀释,将整个混合物过滤通过棉花层。然后在相分离器上分离两相混合物,将有机萃取物蒸发。将粗物料在硅胶上纯化(ISCO,24克柱,历经1分钟梯度从10%到50%EA/己烷),得到部分纯化的产物(254mg)。将物料用苯、然后用石油醚粉碎,得到固体,将其用石油醚洗涤,但是不能与次要组分充分分离开。将混合物在硅胶上再纯化(ISCO,24克柱,30%等度的EA/己烷),得到162mg(48%)作为白色泡沫状物的标题化合物。参见表2的表征数据。
实施例25:5-(2-氰基丙-2-基)-2-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯甲腈(175)。
步骤A:制备2-溴-5-(羟基甲基)苯甲腈
在干燥的100mL圆底烧瓶中在N2气氛下,向2-溴-5-甲酰基苯甲腈(1g,4.76mmol)在干燥EtOH(23.81ml)的冰浴温度的磁力搅拌混合物中添加NaBH4(0.216g,5.71mmol)。将反应混合物在降低的温度搅拌,使其在一夜之后升温至室温。将反应混合物蒸发至干燥,将粗残余物用NH4Cl饱和水溶液稀释并搅拌30分钟。然后,在继续搅拌下添加2N HCl,直到停止鼓泡。将所得白色沉淀物抽吸过滤并风干,得到688mg(65%)作为白色固体的标题化合物。1H NMR(400MHz,DMSO)δ7.84(d,J=5.1Hz,1H),7.83(s,1H),7.61-7.57(m,1H),5.57(s,1H),4.51(s,2H)。13C NMR(101MHz,DMSO)δ143.50,132.86,132.85,132.26,122.08,117.30,113.98,61.27。ESIMS m/z 212.0[M+H]+。
步骤B:制备2-溴-5-(氯甲基)苯甲腈
在干燥的50mL圆底烧瓶中,向2-溴-5-(羟基甲基)苯甲腈(0.5g,2.358mmol)在干燥DCM(11.79ml)的冰浴温度的磁力搅拌混合物中添加氯化亚砜(0.344ml,4.72mmol)。添加DMF(0.5mL)以促进溶解。将反应混合物在降低的温度搅拌15min,然后使其升温至室温。在1h之后,GC-MS分析表明反应完全。将反应混合物用DCM和NaHCO3饱和水溶液稀释,然后剧烈搅拌30min。使各层分离,将水层再次用DCM萃取,将合并的DCM萃取物用硫酸钠干燥,使其过滤通过相分离器。将DCM蒸发,得到485mg(56%)作为白色蜡状物的标题化合物。1H NMR(400MHz,CDCl3)δ7.70(d,J=3.8Hz,1H),7.68(d,J=2.1Hz,1H),7.48(dd,J=8.4,2.3Hz,1H),4.54(s,2H)。13C NMR(101MHz,CDCl3)δ137.70,134.03,133.82,133.60,125.14,116.62,116.36,43.93。GC-MS m/z 231。
步骤C:制备2-溴-5-(氰基甲基)苯甲腈
在干燥的25mL小瓶中在N2气氛下,向2-溴-5-(氯甲基)苯甲腈(0.485g,2.104mmol)在干燥DMSO(5.26ml)的磁力搅拌的混合物中添加氰化钠(0.155g,3.16mmol)。将反应混合物在室温搅拌过夜。GC-MS表明反应完全。将混合物用NaHCO3饱和水溶液稀释,并用醚萃取(3x)。将合并的醚萃取物用硫酸钠干燥,过滤,并蒸发。将粗物料在硅胶上纯化(ISCO,40克柱,历经20分钟梯度达到80%丙酮/己烷,监测仪UV@220nm),得到372mg(72%)作为橙色蜡状物的标题化合物。1H NMR(400MHz,CDCl3)δ7.74(d,J=8.4Hz,1H),7.64(d,J=2.3Hz,1H),7.46(dd,J=8.3,2.3Hz,1H),3.78(s,2H)。13C NMR(101MHz,CDCl3)δ134.06,133.48,133.29,130.30,125.27,116.90,116.32,23.00。GC-MS m/z 220。
步骤D:制备2-溴-5-(2-氰基丙-2-基)苯甲腈
在干燥的50mL圆底烧瓶中在N2气氛下,向2-溴-5-(氰基甲基)苯甲腈(0.372g,1.683mmol)在干燥THF(8.41ml)的冰浴温度的磁力搅拌混合物中添加NaH(0.202g,5.05mmol)。将反应混合物在降低的温度搅拌5min,然后添加碘甲烷(0.316ml,5.05mmol),使反应混合物在一夜之后升温至室温。将反应混合物用醚和NH4Cl饱和水溶液稀释,使各层分离。将水层再次用醚萃取,将合并的醚萃取物用硫酸钠干燥,使其过滤通过硅胶层,并蒸发,得到419mg(95%)作为黄色蜡状物的标题化合物。1H NMR(400MHz,CDCl3)δ7.74(s,1H),7.73(d,J=6.0Hz,1H),7.60(dd,J=8.5,2.5Hz,1H),1.74(s,6H)。13C NMR(101MHz,CDCl3)δ141.88,133.86,130.99,130.88,124.86,122.87,116.69,116.60,36.85,28.82。GCMS m/z248。
步骤E:制备5-(2-氰基丙-2-基)-2-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯甲腈
在干燥的10mL微波小瓶中在氩气气氛下,向5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)嘧啶(0.5g,1.010mmol)在干燥甲苯(4.45ml)和乙醇(0.297ml)的磁力搅拌的混合物中添加磷酸钾(0.643g,3.03mmol)、2-溴-5-(2-氰基丙-2-基)苯甲腈(0.377g,1.514mmol)、四(三苯基膦)钯(0)(0.117g,0.101mmol)、和水(0.297ml)。将反应混合物用氩气吹洗1min,然后将其在BiotageInitiator微波器中在110℃在搅拌下加热30min。将粗物料在硅胶上纯化(ISCO,克柱,历经15分钟梯度达到50%醚/DCM),得到214mg(49%)作为白色泡沫状物的标题化合物。1H NMR(400MHz,CDCl3)δ9.24(s,2H),9.10(s,1H),8.75(d,J=1.6Hz,1H),8.02(dd,J=8.3,2.3Hz,1H),7.95-7.91(m,1H),7.90(d,J=2.0Hz,1H),7.86(dd,J=8.3,2.1Hz,1H),7.58(d,J=8.2Hz,1H),5.81(s,1H),1.80(s,6H),1.10(s,9H)。13CNMR(126MHz,CDCl3)δ161.16,157.01,156.41,146.60,142.76,140.39,136.75,136.73,132.24,130.71,130.63,130.44,123.12,122.12,122.08,117.50,112.30,40.25,36.95,28.90,26.30。ESIMS m/z 412.5[M+H]+。
实施例26:制备2-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)-3-(甲硫基)苯基)-2-甲基丙腈(216)
步骤A:制备2-(3-氟-4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)-2-甲基丙腈
标题化合物(159)由5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)嘧啶和2-(4-溴-3-氟苯基)-2-甲基丙腈根据实施例24C中所述的条件制备并以43%收率分离为棕色油状物。参见表2的表征数据。
步骤B:制备2-(4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)-3-(甲硫基)苯基)-2-甲基丙腈。
在干燥的5mL微波小瓶中在N2气氛下,向2-(3-氟-4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)-2-甲基丙腈(50mg,0.124mmol)在干燥DMSO(1.648mL)的磁力搅拌的混合物中添加甲硫醇钠(43.3mg,0.618mmol)。将反应混合物在微波器中在100℃搅拌45min,然后在室温搅拌过夜。UPLC-MS分析表明~75%的转化率。使反应混合物再次经历在微波器中在100℃加热30min。将反应混合物冷却至室温并直接负载到硅胶上。将粗物料在硅胶上纯化(ISCO,24克柱,历经20min梯度逐步从0%到10%到20%等到60%醚/己烷),得到仅部分纯化的物料。将包含产物的级分合并,将其蒸发,将物料再次在硅胶上纯化(ISCO,24克柱,梯度从0到50%醚/DCM),得到45mg(76%)作为白色泡沫状物的标题化合物。1H NMR(300MHz,CDCl3)δ9.23(s,2H),9.09(s,1H),8.59(dd,J=2.0,1.0Hz,1H),7.86(d,J=2.1Hz,1H),7.84(d,J=1.0Hz,1H),7.44(d,J=1.9Hz,1H),7.31(dd,J=8.0,2.0Hz,1H),7.22(d,J=8.0Hz,1H),6.30(s,1H),2.42(s,3H),1.79(s,6H),1.09(s,9H)。13CNMR(126MHz,CDCl3)δ159.25,158.68,156.90,156.43,147.21,142.40,138.62,137.54,137.11,135.79,134.67,130.58,124.07,122.80,121.73,121.49,40.14,37.26,29.11,26.35,15.97。ESIMS m/z 433.5[M+H]+。
实施例27:制备1-(嘧啶-5-基)-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丁-2-炔-1-醇(199)。
步骤A:制备N-甲氧基-N-甲基嘧啶-5-甲酰胺。
在氮气气氛下向嘧啶-5-甲酸(2.5g,20.15mmol)和N,O-二甲基羟胺盐酸盐(2.49g,25.5mmol)在DCM(50mL)的搅拌混合物中添加EDC·HCl(4.63g,24.17mmol)和DMAP(3.69g,30.2mmol)。将所得反应混合物在室温搅拌14h。将反应混合物减压浓缩;将所得粗物料通过快速柱色谱纯化(100-200,SiO2,50-70%EA/己烷),得到作为浅棕色液体的N-甲氧基-N-甲基嘧啶-5-甲酰胺。产物通过1H NMR和LCMS确认。(2.8g,83%)。1H NMR(400MHz,CDCl3)δ9.28(s,1H),9.10(s,2H),3.59(s,3H),3.41(s,3H);ESIMS m/z 167.97[M+H]+。
步骤B:制备(5-溴吡啶-2-基)(嘧啶-5-基)甲酮。
在0℃向5-溴-2-碘吡啶(5g,17.60mmol)在干燥THF(50mL)的搅拌溶液中添加异丙基氯化镁(2.0M,9.7mL,19.36mmol),在0℃将反应混合物搅拌15min,然后添加在干燥THF(10mL)中的N-甲氧基-N-甲基吡嗪-2-甲酰胺(3.2g,19.36mmol)。将所得反应混合物在室温搅拌2h。然后,将反应混合物用NH4Cl饱和溶液淬灭,并用EtOAc萃取。将有机层用盐水洗涤,用Na2SO4干燥,过滤并减压浓缩。将所得粗产物通过柱色谱纯化(100-200目硅胶),得到作为浅黄色固体的(5-溴吡啶-2-基)(吡嗪-2-基)甲酮(2)(2g,43%)。1H NMR(300MHz,CDCl3)δ9.49(s,2H),9.38(s,1H),8.82(s,1H),8.12(d,J=2.1Hz,2H);ESIMS m/z 264.10[M+H]+。
步骤C:制备嘧啶-5-基(5-(4-(三氟甲氧基)苯基)吡啶-2-基)甲酮。
向5-溴吡啶-2-基)(嘧啶-5-基)甲酮(1.0g,3.816mmol)在干燥THF(25mL)的搅拌溶液中添加4-(三氟甲氧基)苯基硼酸(0.930g,4.580mmol)和K3PO4(2.57g,11.450mmol)。然后将反应混合物用氩气脱气5min,添加X-phos(70mg,4mol%)和Pd(OAc)2(50mg,2mol%),将反应混合物在闭合的容器中加热至70-80℃并保持5h。将反应混合物冷却至室温,用水稀释并用乙酸乙酯(3x 20mL)萃取。将合并的有机层用无水MgSO4干燥,将挥发物减压移除。将所得粗物料通过柱色谱用20-25%乙酸乙酯在己烷中洗脱来纯化,得到作为浅黄色固体的嘧啶-5-基(5-(4-(三氟甲氧基)苯基)吡啶-2-基)甲酮(3)(1.0g,63%);1H NMR(400MHz,CDCl3)δ9.55(s,2H),9.39(s,1H),8.84(d,J=1.5Hz,1H),8.33(dd,J=2.4,8.0Hz,1H),8.16(dd,J=2.4,8.0Hz,1H),7.70(d,J=8.0Hz,2H),7.40(d,J=8.0Hz,2H);ESIMS m/z346.47[M+H]+。
步骤D:制备1-(嘧啶-5-基)-1-(5-(4-(三氟甲氧基)苯基)吡啶-2-基)丁-2-炔-1-醇。
将嘧啶-5-基(5-(4-(三氟甲氧基)苯基)吡啶-2-基)甲酮(0.505g,1.464mmol)在干燥THF(17mL)的搅拌溶液冷却至-78℃,添加丙-1-炔-1-基溴化镁(0.5M,8.78mL,4.39mmol)并在-78℃搅拌1h。将反应混合物用NH4Cl饱和水溶液淬灭并用乙酸乙酯萃取。将有机层用盐水洗涤,用Na2SO4干燥,过滤并减压浓缩。将粗产物通过柱色谱纯化(100-200目硅胶),得到350mg(62%)作为棕色粘性液体的标题化合物。参见表2的表征数据。
实施例28:制备2-(4-(6-(1-羟基-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙基)吡啶-3-基)-3-甲基苯基)-2-甲基丙腈(129)。
步骤A:制备N,4-二甲氧基-N-甲基嘧啶-5-甲酰胺。
在装备有搅拌棒的500mL单颈烧瓶中,将4-甲氧基嘧啶-5-甲酸(8.0g,33.2mmol)和N,O-二甲基羟胺盐酸盐(4.30g,43.2mmol)在DCM(166ml)中搅拌。添加DMAP(6.15g,49.8mmol)和EDC盐酸盐(7.72g,39.9mmol)。将混合物在18℃搅拌64h,然后将硅胶(~50g)添加到反应混合物中。将黄色悬浮液浓缩,然后负载到硅胶(~100g)上。使用EtOAc层析通过硅胶柱(80g)。将产物级分浓缩,得到2.4g(36%)作为无色油状物的标题化合物,其无需进一步纯化即可使用。1H NMR(400MHz,CDCl3)δ8.81(s,1H),8.48(s,1H),4.05(d,J=0.7Hz,3H),3.55(s,3H),3.35(s,3H)。
步骤B:制备(5-溴吡啶-2-基)(4-甲氧基嘧啶-5-基)甲酮。
在装备有氮气入口和温度探针的3-颈250mL烧瓶中,将5-溴-2-碘吡啶(5.02g,17.34mmol)在THF(28.9ml)中在-15℃进行搅拌。逐滴添加异丙基氯化镁(2M,THF)(8.67ml,17.34mmol),以保持T<-10℃。将棕色悬浮液在-10℃搅拌1h。逐滴添加N,4-二甲氧基-N-甲基嘧啶-5-甲酰胺(2.4g,11.56mmol)在THF(20mL)中的溶液,以保持T=-10℃。在-10℃搅拌30min(固体溶解)之后,使冷浴置于原来的位置,使混合物升温。在3h之后,温度已达到5℃。添加1N HCl(20mL),以将pH调节至~7。将混合物用EtOAc(2x 100mL)萃取。将合并的萃取物用Na2SO4干燥,过滤并浓缩,得到黄色油状物。使用DCM将粗物料负载于硅胶(25g)上,使用40%EtOAc/己烷使其在硅胶(80g)上进行层析,得到2.19g(61%)作为米色固体的标题化合物。1H NMR(400MHz,CDCl3)δ8.91(d,J=1.7Hz,1H),8.74-8.66(m,2H),8.06(dd,J=8.3,2.1Hz,1H),8.03-7.97(m,1H),3.95(d,J=1.7Hz,3H)。HRMS-ESI(m/z)[M+H]+,对于C11H9BrN3O2,计算值为293.9873;实测值为293.9873。
步骤C:制备1-(5-溴吡啶-2-基)-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙-1-醇。
在装备备有搅拌棒、温度探针和氮气入口的2200mL单颈烧瓶中,将(5-溴吡啶-2-基)(4-甲氧基嘧啶-5-基)甲酮(2.19g,7.07mmol)在THF(60mL)中搅拌。将溶液冷却至-75℃。通过注射器逐滴添加叔丁基氯化镁(2M,Et2O)(4.24mL,8.49mmol),从而保持T<-70℃。将橙色混合物在-75℃搅拌。在1h之后,移走冷浴,将混合物用0.5N HCl(17mL)迅速但小心地淬灭(最终pH~7)。将混合物用EtOAc(2x 50mL)萃取。将合并的萃取物用Na2SO4干燥,过滤并浓缩,得到橙色油状物。将油状物溶解于DCM并负载于硅胶(25g)上。经快速柱色谱纯化(硅胶,25-40%EtOAc/己烷)得到1.38g(50%)作为黄色油状物的标题化合物。1H NMR(500MHz,CDCl3)δ9.12(s,1H),8.66(s,1H),8.58(dd,J=2.4,0.5Hz,1H),7.77(dd,J=8.7,2.4Hz,1H),7.61(dd,J=8.5,0.6Hz,1H),5.44(s,1H),3.84(s,3H),1.11(s,9H)。HRMS-ESI(m/z)[M+H]+,对于C15H19BrN3O2,计算值为352.0655;实测值为352.0649。
步骤D:制备5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)-4-甲氧基嘧啶。
在装备有搅拌棒、温度探针和氮气入口的200mL单颈烧瓶中,将1-(5-溴吡啶-2-基)-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙-1-醇(1.38g,3.53mmol)在二氧杂环己烷(35.3ml)中搅拌。添加乙酸钾(0.454g,4.58mmol)和4,4,4',4',5,5,5',5'-八甲基-2,2'-二(1,3,2-二氧硼戊环)(0.904g,3.53mmol)。将混合物用氮气喷射5min。添加Pd(dppf)Cl2(0.131g,0.176mmol)。将混合物加热至85℃。在3h之后,通过UPLC没有检测到起始原料。将混合物冷却至室温。将混合物用DCM(50mL)稀释,将其过滤通过Celite。将滤液浓缩至干燥,得到黑色泡沫状物。使粗泡沫状物吸收进DMSO(~8mL)和MeOH(~3mL),将其经反相色谱纯化(C18,250g,30-70%ACN/水),得到750mg(36%)作为白色固体的标题化合物,其无需进一步纯化即可原样使用。1H NMR(400MHz,CDCl3)δ9.27(s,1H),8.85(s,1H),8.65(s,1H),8.33(q,J=8.1Hz,2H),3.85(s,3H),1.44-0.84(m,33H)。
步骤E:制备2-(4-(6-(1-羟基-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙基)吡啶-3-基)-3-甲基苯基)-2-甲基丙腈。
在N2气氛下在干燥的5mL微波小瓶中,向5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)-4-甲氧基嘧啶(100mg,0.190mmol)在干燥甲苯(2285μl)的磁力搅拌的混合物中添加2-(4-溴-3-甲基苯基)-2-甲基丙腈(54.4mg,0.228mmol)(按24A中所述制备)、氟化铯(87mg,0.571mmol)、和四(三苯基膦)钯(0)(22.00mg,0.019mmol)。添加EtOH(762μl)和水(762μl),将反应混合物用氩气吹洗1min。将反应混合物在Biotage Initiator微波器中在110℃搅拌30min,冷却至室温,并负载于Celite干法负载的滤芯(dry-load cartridge)上。将粗物料在硅胶上纯化(ISCO,24克柱,历经15min梯度达到50%醚/DCM),得到40mg(46.4%)作为透明粘性油状物的标题化合物。参见表2的表征数据。
实施例29:制备2-(3-乙基-4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)-2-甲基丙腈(112)。
步骤A:制备4-溴-3-乙基苯甲醛。
向200mL圆底烧瓶中中添加1-溴-2-乙基-4-碘苯(5.0g,16.08mmol)和乙醚(161mL)。将反应置于惰性气氛下并在干冰/丙酮浴中冷却。然后逐滴添加正丁基锂(6.75mL,16.88mmol)。将反应搅拌20min。然后,添加N,N-二甲基甲酰胺(1.364mL,17.69mmol),当冰浴融化时将反应室温至室温。将反应混合物倒入盐水溶液中并用EtOAc(2x 25mL)萃取。将合并的有机物用MgSO4干燥,过滤,并浓缩。将所得残余物通过快速柱色谱纯化(ISCO 24g硅胶,0-30%EtOAc在己烷中),得到2.95g(85%)作为黄色液体的标题化合物。1H NMR(400MHz,DMSO)δ10.00(s,1H),7.86(t,J=2.2Hz,1H),7.82(dd,J=8.2,3.1Hz,1H),7.66(dt,J=8.2,2.1Hz,1H),2.79(qd,J=7.5,2.5Hz,2H),1.22(td,J=7.5,1.7Hz,3H)。13C NMR(101MHz,DMSO)δ192.25,143.66,135.68,133.36,130.37,130.18,128.31,28.50,13.74。EIMS m/z 213。
步骤B:制备(4-溴-3-乙基苯基)甲醇。
向装入4-溴-3-乙基苯甲醛(2.954g,13.86mmol)的200mL圆底烧瓶中添加THF(100mL)和硼氢化钠(0.551g,14.56mmol)。将反应在室温搅拌过夜。将反应用水淬灭。将所得溶液倒入盐水溶液中并用EtOAc(3x 50mL)萃取。将合并的有机物用MgSO4干燥,过滤并浓缩。将所得残余物通过快速柱色谱纯化(ISCO 40g硅胶,0-20%EtOAc在己烷中),得到2.58g(86%)作为淡黄色液体的标题化合物。1H NMR(400MHz,DMSO)δ7.50(d,J=8.2Hz,1H),7.28(d,J=2.1Hz,1H),7.08(dd,J=8.2,2.2Hz,1H),5.25(t,J=5.7Hz,1H),4.46(d,J=5.7Hz,2H),2.69(q,J=7.5Hz,2H),1.16(t,J=7.5Hz,3H)。13C NMR(126MHz,DMSO)δ142.97,142.57,132.49,128.27,126.43,121.72,62.67,29.20,14.77。EIMS m/z 215。
步骤C:制备1-溴-4-(氯甲基)-2-乙基苯
向装入(4-溴-3-乙基苯基)甲醇(2.576g,11.98mmol)的200mL圆底烧瓶中添加二氯甲烷(DCM)(100mL)、三乙胺(3.34mL,23.95mmol)、和甲磺酰氯(1.120mL,14.37mmol)。将反应在室温搅拌整个周末。将反应倒入盐水溶液中并用另外的DCM(3x 30mL)萃取。将合并的有机物用MgSO4干燥,过滤并浓缩。将所得残余物通过快速柱色谱纯化(ISCO 40g硅胶,0-50%EtOAc在己烷中),得到1.9g(67%)作为透明液体的标题化合物。1H NMR(400MHz,DMSO)δ7.57(d,J=8.2Hz,1H),7.41(d,J=2.2Hz,1H),7.21(dd,J=8.2,2.3Hz,1H),4.73(s,2H),2.70(q,J=7.5Hz,2H),1.17(t,J=7.5Hz,3H)。13C NMR(126MHz,DMSO)δ143.36,138.00,133.15,130.59,128.75,123.77,45.80,29.12,14.55。EIMS m/z 233。
步骤D:制备2-(4-溴-3-乙基苯基)乙腈。
向装入1-溴-4-(氯甲基)-2-乙基苯(1.9g,8.14mmol)的200mL圆底烧瓶中添加DMF(40.7ml)和氰化钾(0.583g,8.95mmol)。将反应搅拌3h。通过GCMS分析显示反应完成~50%。将反应在室温搅拌过夜。将反应倒入Na2CO3饱和溶液中并用EtOAc(3x 40mL)萃取。将合并的有机物用MgSO4干燥,过滤并浓缩。将所得残余物通过快速柱色谱纯化(ISCO 40g硅胶,0-40EtOAc在己烷中),得到1.152g(63%)作为透明液体的标题化合物。1H NMR(400MHz,DMSO)δ7.60(d,J=8.2Hz,1H),7.33(d,J=2.3Hz,1H),7.14(dd,J=8.2,2.4Hz,1H),4.02(s,2H),2.70(q,J=7.5Hz,2H),1.17(t,J=7.5Hz,3H)。13C NMR(126MHz,DMSO)δ143.67,133.39,131.69,129.98,128.09,123.02,119.39,29.13,22.36,14.58。EIMS m/z 224。
步骤E:制备2-(4-溴-3-乙基苯基)-2-甲基丙腈。
向装入2-(4-溴-3-乙基苯基)乙腈(1.052g,4.69mmol)的20mL微波小瓶中添加THF(45.0mL)。将反应在冰水浴中冷却,然后添加叔丁醇钾(1.185g,10.56mmol)。将反应搅拌20min,然后添加碘甲烷(0.646mL,10.33mmol)。将反应搅拌4h。然后将反应倒入盐水溶液中并用EtOAc(2x 30mL)萃取。将合并的有机物用MgSO4干燥,过滤并干燥。将所得残余物通过快速柱色谱纯化(ISCO 40g硅胶,0-30%EtOAc在己烷中),得到1.05g(88%)作为半固体的标题化合物。1H NMR(300MHz,DMSO)δ7.62(d,J=8.4Hz,1H),7.48(d,J=2.5Hz,1H),7.29(dd,J=8.4,2.6Hz,1H),2.73(q,J=7.5Hz,2H),1.68(s,6H),1.18(t,J=7.5Hz,3H)。13CNMR(126MHz,DMSO)δ143.69,141.88,133.31,127.21,125.31,124.79,123.08,36.89,29.35,28.64,14.77。EIMS m/z 252。
步骤F:制备2-(3-乙基-4-(6-(1-羟基-2,2-二甲基-1-(嘧啶-5-基)丙基)吡啶-3-基)苯基)-2-甲基丙腈。
向20mL微波小瓶中装入5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)嘧啶(500mg,1.010mmol)、磷酸钾(536mg,2.52mmol)和二(三苯基膦)氯化钯(II)(35.4mg,0.050mmol)。将容器密封并用N2气体抽气和吹洗(3x)。然后,添加2-(4-溴-3-乙基苯基)-2-甲基丙腈(305mg,1.212mmol)在二氧杂环己烷(5.0mL)中的溶液,然后添加水(1.250mL)。将反应用N2气体抽气和吹洗(3x)。使用微波功率将反应加热至100℃并保持1h。将反应倒入盐水溶液中并用EtOAc(2x 25mL)萃取。将合并的有机物用MgSO4干燥,过滤并浓缩。将所得残余物通过快速柱色谱(ISCO 40g硅胶,0-70%EtOAc在己烷中)和反相色谱(ISCO 100g C18,5-100%ACN在H2O中)纯化,得到225mg(53%)作为白色泡沫状物的标题化合物。参见表2的表征数据。
实施例30:制备1-(4-甲氧基嘧啶-5-基)-2,2-二甲基-1-(5-(2,2,2-三氟乙氧基)-[2,3'-联吡啶]-6'-基)丙-1-醇(119)
步骤A:制备N,4-二甲氧基-N-甲基嘧啶-5-甲酰胺。
在装备有搅拌棒的500mL单颈烧瓶中,将4-甲氧基嘧啶-5-甲酸(8.0g,33.2mmol)和N,O-二甲基羟胺盐酸盐(4.30g,43.2mmol)在DCM(166ml)中搅拌。添加DMAP(6.15g,49.8mmol)和EDC盐酸盐(7.72g,39.9mmol)。将混合物在18℃搅拌64h,然后将硅胶(~50g)添加到反应混合物中。将黄色悬浮液浓缩,然后负载于硅胶(~100g)上。使用EtOAc层析通过硅胶柱(80g)。将产物级分浓缩,得到2.4g(36%)作为无色油状物的标题化合物,其无需进一步纯化即可使用。1H NMR(400MHz,CDCl3)δ8.81(s,1H),8.48(s,1H),4.05(d,J=0.7Hz,3H),3.55(s,3H),3.35(s,3H)。
步骤B:制备(5-溴吡啶-2-基)(4-甲氧基嘧啶-5-基)甲酮。
在装备有氮气入口和温度探针的3-颈250mL烧瓶中,将5-溴-2-碘吡啶(5.02g,17.34mmol)在THF(28.9ml)中在-15℃进行搅拌。逐滴添加异丙基氯化镁(2M,THF)(8.67ml,17.34mmol),以保持T<-10℃。将棕色悬浮液在-10℃搅拌1h。逐滴添加N,4-二甲氧基-N-甲基嘧啶-5-甲酰胺(2.4g,11.56mmol)在THF(20mL)中的溶液,以保持T=-10℃。在-10℃搅拌30min之后,使冷浴置于原来的位置,使混合物升温。在3h之后,温度已达到5℃。添加1N HCl(20mL),以将pH调节至~7。将混合物用EtOAc(2x 100mL)萃取。将合并的萃取物用Na2SO4干燥,过滤并浓缩,得到黄色油状物。使用DCM将粗物料负载于硅胶(25g)上,使用40%EtOAc/己烷使其在硅胶(80g)上进行层析,得到2.19g(61%)作为米色固体的标题化合物。1H NMR(400MHz,CDCl3)δ8.91(d,J=1.7Hz,1H),8.74-8.66(m,2H),8.06(dd,J=8.3,2.1Hz,1H),8.03-7.97(m,1H),3.95(d,J=1.7Hz,3H)。HRMS-ESI(m/z)[M+H]+,对于C11H9BrN3O2,计算值为293.9873;实测值为293.9873。
步骤C:制备1-(5-溴吡啶-2-基)-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙-1-醇。
在装备有搅拌棒、温度探针和氮气入口的200mL单颈烧瓶中,将(5-溴吡啶-2-基)(4-甲氧基嘧啶-5-基)甲酮(2.19g,7.07mmol)在THF(60ml)中搅拌。将溶液冷却至-75℃。通过注射器逐滴添加叔丁基氯化镁(2M,Et2O)(4.24ml,8.49mmol),以保持T<-70℃。将橙色混合物在-75℃搅拌。在1h之后,移走冷浴,将混合物用0.5N HCl(17mL)迅速但小心地淬灭(最终pH~7)。将混合物用EtOAc(2x 50mL)萃取。将合并的萃取物用Na2SO4干燥,过滤并浓缩,得到橙色油状物。将油状物溶解于DCM并负载于硅胶(25g)上。经过在硅胶上(80g)使用25-40%EtOAc/己烷的快速柱色谱进行纯化得到1.38g(50%)作为黄色油状物的标题化合物。1H NMR(500MHz,CDCl3)δ9.12(s,1H),8.66(s,1H),8.58(dd,J=2.4,0.5Hz,1H),7.77(dd,J=8.7,2.4Hz,1H),7.61(dd,J=8.5,0.6Hz,1H),5.44(s,1H),3.84(s,3H),1.11(s,9H)。HRMS-ESI(m/z)[M+H]+,对于C15H19BrN3O2,计算值为352.0655;实测值为352.0649。
步骤D:制备5-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)-4-甲氧基嘧啶。
在装备有搅拌棒、温度探针和氮气入口的200mL单颈烧瓶中,将1-(5-溴吡啶-2-基)-1-(4-甲氧基嘧啶-5-基)-2,2-二甲基丙-1-醇(1.38g,3.53mmol)在二氧杂环己烷(35.3ml)中搅拌。添加乙酸钾(0.454g,4.58mmol)和4,4,4',4',5,5,5',5'-八甲基-2,2'-二(1,3,2-二氧硼戊环)(0.904g,3.53mmol)。将混合物用氮气喷射5min。添加Pd(dppf)Cl2(0.131g,0.176mmol)。将混合物加热至85℃。在3h之后,通过UPLC没有检测到起始原料。将混合物冷却。将混合物用DCM(50mL)稀释,将其过滤通过Celite。将滤液浓缩至干燥,得到黑色泡沫状物。使粗泡沫状物吸收进DMSO(~8mL)和MeOH(~3mL),使用30-70%ACN/水将其在C18(250g)上层析,得到750mg(36%)作为白色固体的标题化合物,其无需进一步纯化即可使用。1H NMR(400MHz,CDCl3)δ9.27(s,1H),8.85(s,1H),8.65(s,1H),8.33(q,J=8.1Hz,2H),3.85(s,3H),1.44-0.84(m,33H)。
步骤E:制备2-溴-5-(2,2,2-三氟乙氧基)吡啶
在室温在惰性气氛下向6-溴吡啶-3-醇(1g,5.73mmol)在丙酮(20ml)的搅拌溶液中添加三氟甲磺酸2,2,2-三氟乙基酯(2.01g,8.67mmol)然后添加K2CO3(1.17g,8.67mmol)。将反应混合物在60℃加热2h。然后,将反应混合物用冰冷的水(20mL)稀释并用EtOAc(2x50mL)萃取。将合并的有机层用无水Na2SO4干燥并减压浓缩。将所得粗物料通过柱色谱(SiO2,100-200目)使用30%EtOAc在石油醚中作为洗脱液进行纯化,得到标题化合物(0.8g,54%)。1H NMR(400MHz,CDCl3)δ8.12(d,J=3.6Hz,1H),7.43(d,J=8.8,1H),7.20-7.15(m,1H),4.39(q,J=8.0Hz,2H);ESIMS m/z 256[M+H]+。
步骤F:制备1-(4-甲氧基嘧啶-5-基)-2,2-二甲基-1-(5-(2,2,2-三氟乙氧基)-[2,3'-联吡啶]-6'-基)丙-1-醇(119)
在N2气氛下向15-(2,2-二甲基-1-((4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)氧基)-1-(5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶-2-基)丙基)-4-甲氧基嘧啶(0.43g,0.83mmol)、2-溴-5-(2,2,2-三氟乙氧基)吡啶(0.169g,0.66mmol)和碳酸钠(0.28g,2.64mmol)在二氧杂环己烷(6mL)和水(2mL)的脱气溶液中添加PdCl2(dppf)(0.054g,0.007mmol)。将反应混合物在85℃搅拌16h。将反应混合物用冰冷的水淬灭并用EtOAc萃取。将有机层用盐水洗涤,用Na2SO4干燥,过滤并减压浓缩。将粗产物通过柱色谱使用20%EtOAc/石油醚作为洗脱液纯化,得到作为棕色油状物的标题化合物(99mg,33%)。参见表2的表征数据。
生物学实施例
实施例A:评价杀真菌活性:小麦斑枯病(禾生球腔菌(Mycosphaerellagraminicola);无性型:小麦叶斑病病原菌;Bayer编码SEPTTR):
对于类型A试验,将以下表4中的技术级实验杀真菌剂溶解于丙酮,然后与9体积的包含110ppm Triton X-100的水混合。使用自动亭式喷雾器将杀真菌剂溶液施用到小麦幼苗上。对于类型B试验,以10%(w/v)制备以下表4中的技术级实验杀真菌剂的可乳化浓缩物(EC)制剂,然后将其与150体积的0.1%Trycol 5941混合。使用自动追踪式喷雾器以200L/ha将这些溶液施用于小麦幼苗上。使所有经喷雾的植物在进一步处理前风干。
在温室中,使小麦植物(Yuma品种)在50%矿质土壤/50%无土Metro混合物中从种子开始生长直到第一片叶完全形成,每罐7-10株幼苗。在施用实验杀真菌剂之前或之后,用标准实验室SEPTTR分离株(SI SEPTTR)的孢子或用来自从英格兰维尔斯本在2012年收集的SEPTTR野生型分离株(FI SEPTTR)的孢子接种植物。在接种之后,使植物在20℃在100%相对湿度保持3天(黑暗露水室中保持一天,然后在有光照的露水室中保持两天)。植物接着转移至设置为20℃的温室,使病害发展。当病害症状完全表现于未处理植物时,基于0%至100%的病害严重度分级,评价处理植物上的感染程度。使用对于处理的植物相对于未处理的植物的病害严重度之比计算病害控制百分比。结果显示于以下表4。
表1.结构和制备方法。
表2.分析数据。
表3.小麦斑枯病试验(SEPTTR)中病害防治的评级标准。
%病害防治 | 评级 |
80-100 | A |
60-79 | B |
40-59 | C |
<40 | D |
未测试 | E |
表4.生物学活性-以高体积施用和低体积试验进行的病害防治。
*SI-SEPTTR标准实验室分离株
*FI-SEPTTR野生型分离株
*SEPTTR-小麦斑枯病(小麦叶斑病病原菌)
*ppm-份每百万份
*g/ha-克每公顷
*1DP-施用保护剂1天
*3DC-治疗3天
*3DP-施用保护剂3天
Claims (49)
1.式I的化合物或其盐,其中:
Z是任选取代的5-嘧啶基,任选取代的4-嘧啶基,任选取代的噻唑基,任选取代的唑基,任选取代的3-吡啶基,或任选取代的4-吡啶基;
n为0或1;
R1是脂族饱和烃基,卤代脂族饱和烃基,芳基,或杂芳基,它们各自任选取代有0个、1个、2个或3个独立的R4;
R2是芳基,杂芳基芳氧基,杂芳氧基,芳基炔基,杂芳基炔基,芳基脂族饱和烃基,杂芳基脂族饱和烃基,芳基脂族饱和烃基氧基,杂芳基脂族饱和烃基氧基,芳氧基脂族饱和烃基,或杂芳氧基脂族饱和烃基,其中各芳基或杂芳基任选取代有0个、1个、2个或3个独立的R4;
R3独立地为H,脂族饱和烃基,芳基,取代的芳基,杂芳基,芳基脂族饱和烃基,或杂芳基脂族饱和烃基,-C(O)脂族饱和烃基,-C(O)芳基,-Si(脂族饱和烃基)3,它们各自任选取代有0个、1个、2个或3个独立的R4;
R4独立地为芳基,杂芳基,脂族饱和烃基,硫代脂族饱和烃基,氰基,卤代脂族饱和烃基,氰基脂族饱和烃基,羟基,脂族饱和烃基氧基,卤素,卤代脂族饱和烃基氧基,-C(O)脂族饱和烃基,-C(O)OH,-C(O)O脂族饱和烃基,-SCF3,-SF5,-SCN,或SO2(芳基);和
R5-R7独立地选自H,脂族饱和烃基,脂族饱和烃基氧基,卤素,和卤代脂族饱和烃基;
条件是当n=1时,Z是1-四唑基或5-嘧啶基。
2.权利要求1的化合物,其中R2是任选取代有1个、2个或3个独立的R4的芳基或杂芳基。
3.权利要求2的化合物,其中R1是任选取代有1个、2个或3个独立的R4的脂族饱和烃基、卤代脂族饱和烃基、环脂族饱和烃基、芳基、或杂芳基芳基。
4.权利要求3的化合物,其中R1是甲基,乙基,叔丁基,异丙基,环丙基,三氟甲基,2,4-二氟苯基,2-氟-4-氯苯基,-CF2-(2,4-二氟苯基),-CF2-(2-氟-4-氯苯基),-CH2-(2,4-二氟苯基),或-CH2-(2-氟-4-氯苯基)。
5.权利要求2的化合物,其中Z是任选取代的5-嘧啶基,任选取代的4-嘧啶基,任选取代的3-吡啶基,任选取代的4-吡啶基;或当n=1时,Z是1-四唑基。
6.权利要求5的化合物,其中Z是5-嘧啶基或3-吡啶基且n=0。
7.权利要求5的化合物,其中Z是5-嘧啶基、3-吡啶基或1-四唑基且n=1。
8.权利要求2的化合物,其中R2是任选取代有1个、2个或3个独立的R4的苯基、2-吡啶基、3-吡啶基、或5-嘧啶基。
9.权利要求8的化合物,其中R4是卤素,卤代脂族饱和烃基,氰基脂族饱和烃基,卤代脂族饱和烃基氧基,或氰基。
10.权利要求8的化合物,其中R2是在4位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基或氰基取代基的苯基。
11.权利要求8的化合物,其中R2是在5位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的2-吡啶基。
12.权利要求8的化合物,其中R2是在6位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的3-吡啶基。
13.权利要求1的化合物,其中R2是任选取代有1个、2个或3个独立的R4的芳氧基或杂芳氧基。
14.权利要求13的化合物,其中R1是任选取代有1个、2个或3个独立的R4的脂族饱和烃基、卤代脂族饱和烃基、环脂族饱和烃基、芳基、或杂芳基芳基。
15.权利要求14的化合物,其中R1是甲基,乙基,叔丁基,异丙基,环丙基,三氟甲基,2,4-二氟苯基,2-氟-4-氯苯基,-CF2-(2,4-二氟苯基),-CF2-(2-氟-4-氯苯基),-CH2-(2,4-二氟苯基),或-CH2-(2-氟-4-氯苯基)。
16.权利要求13的化合物,其中Z是任选取代的5-嘧啶基,任选取代的4-嘧啶基,任选取代的3-吡啶基,任选取代的4-吡啶基;或当n=1时,Z是1-四唑基。
17.权利要求16的化合物,其中Z是5-嘧啶基或3-吡啶基且n=0。
18.权利要求16的化合物,其中Z是5-嘧啶基、3-吡啶基或1-四唑基且n=1。
19.权利要求13的化合物,其中R2是任选取代有1个、2个或3个独立的R4的苯氧基、(2-吡啶基)氧基、(3-吡啶基)氧基、或(5-嘧啶基)氧基。
20.权利要求19的化合物,其中R4是卤素,卤代脂族饱和烃基,氰基脂族饱和烃基,卤代脂族饱和烃基氧基,或氰基。
21.权利要求19的化合物,其中R2是在4位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的苯氧基。
22.权利要求19的化合物,其中R2是在5位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的(2-吡啶基)氧基。
23.权利要求19的化合物,其中R2是在6位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的(3-吡啶基)氧基。
24.权利要求19的化合物,其中R2是在6位取代有卤素、卤代脂族饱和烃基、氰基脂族饱和烃基、卤代脂族饱和烃基氧基、或氰基取代基的(3-嘧啶基)氧基。
25.权利要求1任一项的化合物,其中所述化合物抑制选自以下的酶:4-羟基苯基-丙酮酸加双氧酶,5-脂氧合酶,腺苷脱氨酶,醇脱氢酶,氨基肽酶P,血管紧张素转换酶,芳香酶(CYP19),钙调磷酸酶,氨甲酰磷酸合成酶,碳酸酐酶族,儿茶酚氧位甲基移位酶,环氧合酶族,二氢嘧啶脱氢酶-1,DNA聚合酶,法呢基焦磷酸合酶,法呢基移位酶,富马酸还原酶,GABA转氨酶,HIF-脯氨酰羟化酶,组蛋白脱乙酰基酶族,HIV整合酶,HIV-1逆转录酶,异亮氨酸tRNA连接酶,羊毛甾醇脱甲基酶(CYP51),基质金属蛋白酶家族,甲硫氨酸胺基肽酶,中性肽链内切酶,一氧化氮合酶族,磷酸二酯酶III,磷酸二酯酶IV,磷酸二酯酶V,丙酮酸铁氧化还原蛋白氧化还原酶,肾肽酶,核糖核苷二磷酸还原酶,凝血烷合酶(CYP5a),甲状腺过氧化酶,酪氨酸酶,脲酶,和黄嘌呤氧化酶。
26.权利要求1任一项的化合物,其中所述化合物抑制选自以下的酶:1-脱氧-d-木酮糖-5-磷酸还原异构酶(DXR),17-α羟化酶/17,20-裂解酶(CYP17),醛固酮合酶(CYP11B2),氨基肽酶P,炭疽致死因子,精氨酸酶,β-内酰胺酶,细胞色素P450 2A6,d-丙氨酸d-丙氨酸连接酶,多巴胺β-羟化酶,内皮素转换酶-1,谷氨酸羧肽酶II,谷氨酰环化酶,乙二醛酶,血红素氧合酶,HPV/HSV E1解旋酶,吲哚胺2,3-加双氧酶,白三烯A4水解酶,甲硫氨酸氨基肽酶2,肽脱甲酰基酶,磷酸二酯酶VII,松弛酶,视黄酸羟化酶(CYP26),TNF-α转换酶(TACE),UDP-(3-O-(R-3-羟基肉豆蔻酰))-N-乙酰葡糖胺脱乙酰基酶(LpxC),血管粘附蛋白-1(VAP-1),和维生素D羟化酶(CYP24)。
27.权利要求1任一项的化合物,其中所述化合物抑制(或确定为抑制)羊毛甾醇脱甲基酶(CYP51)。
28.权利要求1任一项的化合物,其中所述化合物确定为具有对抗靶标有机体的活性范围。
29.治疗患有或易患与金属酶有关的病症或疾病的对象的方法,其中所述对象已经确定为需要治疗与金属酶有关的病症或疾病,所述方法包括给有治疗需要的对象服用有效量的权利要求1的化合物,使得可治疗所述对象的所述病症。
30.治疗患有或易患与金属酶有关的病症或疾病的对象的方法,其中所述对象已经确定为需要治疗与金属酶有关的病症或疾病,所述方法包括给有治疗需要的对象服用有效量的权利要求1的化合物,使得所述对象体内的金属酶活性得以调节(例如,下调,抑制)。
31.权利要求30的方法,其中所述疾病或病症是癌症,心血管病,内分泌疾病,炎性疾病,传染病,妇科疾病,代谢病,眼科疾病,中枢神经系统(CNS)疾病,泌尿系疾病,或肠胃疾病。
32.权利要求30的方法,其中所述疾病或病症是系统性真菌感染,或甲真菌病。
33.治疗或预防植物内或植物上的与金属酶有关的疾病或病症的方法,所述方法包括使权利要求1的化合物与所述植物或种子接触。
34.抑制植物上的微生物内的金属酶活性的方法,所述方法包括使权利要求1的化合物与所述植物或种子接触。
35.治疗或预防植物内或植物上的真菌疾病或病症的方法,所述方法包括使权利要求1的化合物与所述植物或种子接触。
36.治疗或预防植物内或植物上的真菌生长的方法,所述方法包括使权利要求1的化合物与所述植物或种子接触。
37.抑制植物内或植物上的微生物的方法,所述方法包括使权利要求1的化合物与所述植物或种子接触。
38.一种组合物,其包含权利要求1的化合物和农业上可接受的载体。
39.用于防治真菌病原体的组合物,其包括至少一种权利要求1的化合物或至少一种权利要求38的组合物与其它杀虫剂的混合物,所述其它杀虫剂包括杀真菌剂、杀昆虫剂、杀线虫剂、杀螨剂、杀节肢动物剂、杀细菌剂及它们的组合。
40.权利要求39的组合物,其进一步包含选自以下的唑类杀真菌剂:氟环唑(epoxiconazole),戊唑醇(tebuconazole),氟喹唑(fluquinconazole),粉唑醇(flutriafol),叶菌唑(metconazole),腈菌唑(myclobutanil),环唑醇(cycproconazole),丙硫菌唑(prothioconazole)和丙环唑(propiconazole)。
41.权利要求39的组合物,其进一步包含选自以下的甲氧基丙烯酸酯类杀真菌剂:肟菌酯(trifloxystrobin),吡唑醚菌酯(pyraclostrobin),肟醚菌胺(orysastrobin),氟嘧菌酯(fluoxastrobin)和腈嘧菌酯(azoxystrobin)。
42.权利要求39的组合物,其进一步包含选自以下的抑制琥珀酸脱氢酶的(SDHI)杀真菌剂:氟唑菌酰胺(fluxapyroxad),烟酰胺(boscalid),吡噻菌胺(penthiopyrad),苯并烯氟菌唑(benzovindiflupyr),联苯吡菌胺(bixafen),flupyram,和吡唑萘菌胺(isopyrazam)。
43.一种组合物,其包含权利要求1的化合物和药学上可接受的载体。
44.权利要求43的组合物,其进一步包含另外的治疗剂。
45.权利要求43的组合物,其进一步包含另外的治疗剂,所述治疗剂为抗癌剂,抗真菌剂,心血管剂,抗炎剂,化疗剂,抗血管生成剂,细胞毒素剂,抗增殖剂,代谢病剂,眼科疾病剂,中枢神经系统(CNS)疾病剂,泌尿系疾病剂,或肠胃疾病剂。
46.权利要求38-42的组合物,其中所述真菌病原体是以下之一:小麦斑枯病(LeafBlotch of Wheat)(禾生球腔菌(Mycosphaerella graminicola);无性型:小麦叶斑病病原菌(Septoria tritici)),小麦褐锈病(Wheat Brown Rust)(小麦叶锈菌(Pucciniatriticina)),条锈病(Stripe Rust)(小麦条锈菌(Puccinia striiformis)),苹果黑星病(Scab of Apple)(苹果黑星病菌(Venturia inaequalis)),玉米水疱病(Blister Smut ofMaize)(玉米黑粉菌(Ustilago maydis)),葡萄白粉病(Powdery Mildew of Grapevine)(葡萄白粉病(Uncinula necator)),大麦烫伤(Barley Scald)(大麦云纹病菌(Rhynchosporium secalis)),稻瘟病(Blast of Rice)(稻瘟病菌(Magnaporthegrisea)),大豆锈病(Rust of Soybean)(豆薯层锈菌(Phakopsora pachyrhizi)),小麦颖枯病(Glume Blotch of Wheat)(小麦颖枯病菌(Leptosphaeria nodorum)),小麦白粉病(Powdery Mildew of Wheat)(小麦白粉菌(Blumeria graminis f.sp.tritici)),大麦白粉病(Powdery Mildew of Barley)(大麦白粉病菌(Blumeria graminis f.sp.hordei)),瓜类白粉病(Powdery Mildew of Cucurbits)(黄瓜白粉病(Erysiphe cichoracearum)),瓜类炭疽病(Anthracnose of Cucurbits)(瓜类炭疽病(Glomerella lagenarium)),甜菜褐斑病(Leaf Spot of Beet)(甜菜尾孢菌(Cercospora beticola)),番茄绵疫病(EarlyBlight of Tomato)(番茄早疫病菌(Alternaria solani)),和大麦网斑病(Net Blotch ofBarley)(大麦网斑病菌(Pyrenophora teres))。
47.权利要求46的组合物,其中所述真菌病原体是以下之一:小麦斑枯病(Leaf Blotchof Wheat)(小麦叶斑病病原菌(Septoria tritici))、小麦褐锈病(Wheat Brown Rust)(小麦叶锈菌(Puccinia triticina))、和大豆锈病(Rust of Soybean)(豆薯层锈菌(Phakopsora pachyrhizi))。
48.控制和预防真菌侵袭植物的方法,所述方法包括以下步骤:将杀真菌有效量的至少一种权利要求1-24的化合物或至少一种权利要求38-42的组合物施用于以下位置的至少一个:植物,邻近植物的区域,适于支持植物生长的土壤,植物的根部,植物的种子,和植物的叶子。
49.治疗患有或易患病症或疾病的对象的方法,其中所述对象已经确定为需要治疗该病症或疾病,所述方法包括:给所述有治疗需要的对象服用有效量的式(I)的化合物或其盐,其中所述病症或疾病选自以下的一种或多种:浅部真菌感染,粘膜真菌感染,系统性真菌感染,曲霉病,芽生菌病,念珠菌病,着色真菌病,球孢子菌病,隐球菌病,脚气,组织胞浆菌病,角膜真菌病,瘢痕疙瘩性芽生菌病,马拉色菌感染,毛霉菌病,甲真菌病,副球孢子菌病,马尔尼菲青霉菌感染,暗色丝孢霉病,卡氏肺孢子虫性肺炎,和癣(甲癣,头癣,股癣,足癣,发癣,花斑癣)。
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