Some Novel Thiopyrimidine Nucleoside Analogs: Synthesis and In Vitro Antimicrobial Evaluation

Abstract

Some new S-alkyl derivatives of indeno[1′,2′:4,5]thieno[2,3-d]pyrimidine 2–8 were prepared starting with pyrimidine-2(1H)-thione derivative (1). Also, treatment of compound 1 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide or 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose afforded nucleosides 9 and 12, respectively. Furthermore, deprotection of the latter blocked nucleosides was achieved in methanolic ammonia to afford the desired free S-nucleoside derivatives 10 and 13, respectively. Some prepared products were screened for antimicrobial activity, and some of them showed promising activity.

Keywords:

• Acyclic and cyclic nucleosides
• antimicrobial activity
• indenothieno[2,3-d]pyrimidines
• S-alkyl derivatives

ACKNOWLEDGMENT

We are grateful to Deutsche Forschungsgemeinschaft (DFG) and Prof. Klaus Banert, Chemistry Department, Technical University, Chemnitz, Germany, for facilities and support.

Notes

+++ Highly sensitive (21–25 mm); ++ Fairly sensitive (16–20 mm); + Slightly sensitive (15–10 mm); − Not sensitive (0–5 mm).