The Synthesis Of 2-Alkoxy-N~6-Alkyl Adenosine Compounds And Their Anti-Platelet Aggregation Activity

Purine nucleoside compounds have a wide range of applications in the field of anti-virus, anti-tumor and anti-platelet aggregation and so on. So many pharmaceutical and chemical workers have attracted more attention in this area.In this paper, guanosine 1 as a starting material, was protected by acetic anhydride to afford 2',3',5'-tri-O-acetyl-guanosine (2). The key intermediates 2-alkoxy-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosy 1) purine (4a-4c) were then prepared through a series of reactions:chlorinating with phosphorus oxychloride, diazotization with amyl nitrite, hydrolyzation and alkylation with several alkyl halide. Afterwards, the novel 2-alkoxy-N6-alkyl Adenosine compounds (5a-5c) were generated from compounds 4a-4c by aminolysis and deprotection reactions.1H NMR,13C NMR,IR and HRMS for the final compounds 5a-5c were provided in experimental section. What is more, the anti-platelet aggregation rates for the final compounds were measured. At a concentration of 100μmol/L, the test results of the biological activity of anti-platelet aggregation showed that N6-(4-methylbenzyl)-2-benzyloxy adenosine (5c3) and N6-(2-phenethyl)-2-benzyloxy adenosine (5c4) have a relatively low aggregation rate and have a certain anti-platelet aggregation activity.