Synthesis Of 2-Alkylthioadenine Nucleoside Analogs Containing A 2-Propane-1,3-Diester Branched Chain At The 9-Position

Purine nucleoside analogs, as a class of important medicinal compounds, have been widely used in medical fields, such as antivirus, anticancer, anti-thrombosis and so on. In this paper, synthetic route of 2-alkylthioadenine 22 was introduced in five steps:oxidation, hydrolysis, reduction, cycle closing and S-alkylation. Compound 22 reacted with triethyl 3-bromopropane-1,1, 1-tricarboxylate to give triethyl 3-(6-amino-2-alkylthio-purin-9-yl) propane-1, 1,1-tricaboxylate 24. Treatment of 24 with sodium methoxide in methanol generated diester 25, which was reduced in the presence of sodium borohydride to afford the corresponding diol 26. Then 26 reacted with five different acid anhydrides to give 2-(2-(6-amino-2-alkylthio-purin-9-yl) ethyl) propane-1,3-diester 15a-c.24 novel acyclic analogs of 2-alkylthioadenine nucleoside were identified through infrared spectral, nuclear magnetic resonance spectral and mass spectral. In addition, platelet aggregation rates for the final compounds 15a-c were measured.