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有机化学
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有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2205-2211.DOI: 10.6023/cjoc201504036 上一篇    下一篇

研究简报

6-烷氨基-2-乙硫基嘌呤核苷化合物的合成及抗血小板聚集活性研究

王子健a, 李顺来a, 于明武a, 骆媛b, 王帅b, 王永安b, 杜洪光a   

  1. a 北京化工大学理学院 北京 100029;
    b 军事医学科学院毒物药物研究所 抗毒药物与毒理学研究国家重点实验室 北京 100850
  • 收稿日期:2015-04-23 修回日期:2015-06-04 发布日期:2015-06-12
  • 通讯作者: 王永安, 杜洪光 E-mail:yonganw@126.com;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-Alkylamino-2-ethylthiopurine Nucleoside Compounds and Their Antiplatelet Aggregation Activities

Wang Zijiana, Li Shunlaia, Yu Mingwua, Luo Yuanb, Wang Shuaib, Wang Yonganb, Du Hongguanga   

  1. a Beijing University of Chemical Technology, Beijing 100029;
    b Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, State Key Laboratory ofToxicology and Medical Countermeasures, Beijing 100850
  • Received:2015-04-23 Revised:2015-06-04 Published:2015-06-12
  • Supported by:

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

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补充材料

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被引次数

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以鸟苷(1)为原料, 与乙酸酐经过糖环羟基保护反应, 得到2',3',5'-三-O-乙酰基鸟苷(2); 2与对甲苯磺酰氯反应, 得到9-(2',3',5'-三-O-乙酰基-β-D-呋喃核糖)-2-氨基-6-对甲苯磺酰氧基嘌呤(3); 3与亚硝酸异戊酯和二乙基二硫醚反应, 得到9-(2',3',5'-三-O-乙酰基-β-D-呋喃核糖)-6-对甲苯磺酰氧基-2-乙硫基嘌呤(4); 4经过胺解和脱糖环羟基保护反应得到10个未见报道的6-烷氨基-2-乙硫基嘌呤核苷化合物(5). 化合物结构经1H NMR、13C NMR、IR和HRMS进行了表征, 并对它们进行了抗血小板聚集活性测试, 结果表明对抗血小板聚集显示一定的活性.

关键词: 嘌呤衍生物, 合成, 结构表征, 抗血小板聚集活性

Guanosine (1) as the starting material, reacted with acetic anhydride to obtain 2',3',5'-tri-O-acetyl-guanosine (2), which reacted with TsCl to obtain 2-amino-6-tosyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine (3). Compound 3 was diazotized with isoamyl nitrite and then reacted with dialkyl disulfides to afford 2-ethylthio-6-tosyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine (4). Finally, compounds 5 were acquired by aminolysis and deprotection of 4. Ten new compounds were synthesized and all compounds were characterized with 1H NMR, 13C NMR, IR and HRMS. Meanwhile, their antiplatelet aggregation rate was measured. The results show that these compounds have a certain antiplatelet aggregation activity.

Key words: purine derivatives, synthesis, structure characterization, antiplatelet aggregation activity