9-(2-羟基乙基)-6-烷氨基-8-甲氧基-2-烷硫基嘌呤的合成及其抗血小板凝集活性  

Synthesis of 6-Alkylamino-2-alkylthio-9-(2-hydroxyethyl)-8-methoxy-purines and Their Anti-platelet Aggregation Activities

作　　者：汪韬[1] 杜洪光[1] 

机构地区：[1]北京化工大学理学院,北京100029

出　　处：《有机化学》2013年第8期1720-1727,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21272022)资助项目~~

摘　　要：以6-氯鸟嘌呤（1）为原料，与乙酸-2-溴-乙酯反应得到9-乙酰氧基乙基-2-氨基-6-氯嘌呤（2），2经溴代得到9-乙酰氧基乙基-2-氨基-6-氯-8-溴嘌呤（3），3在甲醇中与甲醇钠反应得到9．（2．羟基乙基）-2-氨基-8-甲氧基-6-氯嘌呤（4），对4的羟基进行乙酰化保护得到9-乙酰氧基乙基-2-氨基-8-甲氧基-6-氯嘌呤（5），5经重氮化反应后再与二烷基二硫醚反应得到9-乙酰氧基乙基-8-甲氧基-2-烷硫基-6-氯嘌呤（6），6与胺进行亲核取代反应得到9．乙酰氧基乙基-6-烷氨基-8-甲氧基-2-烷硫基嘌呤（7），7的羟基脱保护后得到9-（2-羟基乙基）-6．烷氨基-8-甲氧基-2-烷硫基嘌呤（8）．合成了24个未见报道的化合物3～8。它们的结构经1HNMR，13CNMR，IR及HRMS等手段得到表征。并对9个目标化合物8进行了抗血小板凝集活性测试．2-Amino-6-chloropurine （1） was reacted with 2-bromoethyl acetate to yield 9-acetoxyethyl-2-amino-6-chloropurine （2）, which was treated with NBS to afford 9-acetoxyethyl-2-amino-8-bromo-6-chloropurine （3）. 3 was reacted with sodium methanol to afford 2-amino-6-chloro-9-（2-hydroxyethyl）-8-methoxypurine （4）, and then 4 was treated with acetic anhydride to yield 9-acetoxyethyl-2-amino-6-chloro-8-methoxypurine （5）. After that 5 was diazotized and reacted with dialkyl disulfide to yield 9-acetoxyethyl-2-alkylthio-6-chloro-8-methoxypurine （6） and 6 was treated with amine to afford 9-acetoxyethyl-6-alkylamino-2-alkylthio-8-methoxypurine （7）. Deprotection of hydroxyl group in compound 7 provided target compound 8. All 24 novel compounds 3-8 were acquired and their structures were identified by 1H NMR, 13C NMR, IR and HRMS techniques. Besides, the anti-platelet aggregation activities of the nine target compounds were tested.

关 键 词：嘌呤衍生物 合成 结构表征 抗血小板凝集 

分 类 号：R914[医药卫生—药物化学]