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以鸟嘌呤核苷(Ⅰ)为原料,经羟基保护得到2’,3’,5’-三-O-乙酰基鸟嘌呤核苷(Ⅱ),Ⅱ与三氯氧磷反应得到2-氨基-6-氯-9-(2’,3’,5’-三-O-乙酰基-β-D-呋喃核糖基)嘌呤(Ⅲ),Ⅲ再进行重氮-烷硫化反应,生成2-烷硫基-6-氯-9-(2’,3’,5’-三-O-乙酰基-β-D-呋喃核糖基)嘌呤(Ⅳ),Ⅳ与醇进行亲核取代反应同时脱去糖环保护得到8个6-烃氧基-2-烷硫基嘌呤腺苷化合物(Ⅴ)。化合物的结构经1HNMR、13CNMR、IR和HRMS表征,同时对合成的目标化合物进行了体外抗血小板凝聚活性测试。结果表明,在测试浓度为10μmol/L时,6-(2-呋喃甲基)氧基-2-丙硫基腺苷具有较高的抗血小板凝聚活性。
Using guanosine (Ⅰ) as raw material, 2 ’, 3’, 5’-tri-O-acetylgoguanosine (Ⅱ) was obtained by hydroxyl protection and reacted with phosphorus oxychloride to obtain 2-amino- The diazotization of 6-chloro-9- (2 ’, 3’, 5’-tri-O-acetyl-β-D-ribofuranosyl) purine (III) Thio-6-chloro-9- (2 ’, 3’, 5’-tri-O-acetyl-β-D-ribofuranosyl) purine (IV) Sugar ring protection gives 8 6-alkoxy-2-alkylthio purine adenosine compounds (V). The structures of the compounds were characterized by 1HNMR, 13CNMR, IR and HRMS. The synthesized target compounds were tested for anti-platelet aggregation activity in vitro. The results showed that 6- (2-furylmethyl) oxy-2-propylthioadenosine had higher anti-platelet aggregation activity at the test concentration of 10 μmol / L.