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有机化学
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有机化学 ›› 2013, Vol. 33 ›› Issue (08): 1741-1748.DOI: 10.6023/cjoc201303017 上一篇    下一篇

研究论文

6-烷氧基-2-丙硫基-8-氮杂嘌呤核苷的合成及抗血小板凝聚活性评价

邓聪迩, 李顺来, 刘祥伟, 杜洪光   

  1. 北京化工大学理学院 北京 100029
  • 收稿日期:2013-03-11 修回日期:2013-04-04 发布日期:2013-04-17
  • 通讯作者: 杜洪光 E-mail:dhg@mail.buct.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21272022)资助项目.

Synthesis of 6-Alkoxyl-2-propylthio-8-azapurine Nucleosides and Their Antiplatelet Aggregation Activity Evaluation

Deng Conger, Li Shunlai, Liu Xiangwei, Du Hongguang   

  1. College of Science, Beijing University of Chemical Technology, Beijing 100029
  • Received:2013-03-11 Revised:2013-04-04 Published:2013-04-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272022).

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3

2-硫代巴比妥酸(1)经过巯基的烷基化、嘧啶环硝化以及羟基的氯代三步反应得到5-硝基-2-丙硫基-4,6-二氯嘧啶(4); 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖(5)经过叠氮取代及叠氮的还原反应得到1-氨基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖(7); 化合物7与4经过亲核取代、硝基还原、重氮化及偶联反应得到9-[(2',3',5'-三-O-苯甲酰基)-β-D-呋喃核糖基]-2-丙硫基-6-氯-8-氮杂嘌呤(10); 化合物10与醇进行亲核取代及脱保护反应后, 得到10个未见报道的6-烷氧基-2-丙硫基-8-氮杂嘌呤核苷化合物(11). 化合物的结构经过1H NMR, 13C NMR, IR以及HRMS得到表征, 并进行了抗血小板凝聚活性测试.

关键词: 8-氮杂嘌呤核苷, 合成, 结构表征, 抗血小板凝聚

2-Thiobarbituric acid (1) was converted to 4,6-dichloro-5-nitro-2-propylthiopyrimidine (4) via S-alkylation, nitration and chlorination. Followed by azide and reduction reaction of azido, 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5) was converted to 1-amino-2,3,5-tri-O-benzoyl-β-D-ribofuranose (7). 9-[(2',3',5'-Tri-O-benzoyl)-β-D-ribofuranosyl]-6-chloro-2-propylthio-8-azapurine (10) was obtained via nucleophilic substitution of 7 with 4, reduction, diazotization and coupling reaction. Nucleophilic displacement of the chloride in 10 with various alcohols and deprotection afforded 6-alkoxyl-2-propylthio-8-azapurine nucleosides (11). Their structures were identified by 1H NMR, 13C NMR, IR and HRMS techniques. Moreover, the antiplatelet aggregation activities of compounds 11 were measured.

Key words: 8-azapurine nucleosides, synthesis, characterization, antiplatelet aggregation