Synthesis and pharmacological evaluation of novel (3aS)-2-substituted perhydro-25-pyrrolo[1,2-c][1,3,2]oxazaphosphole-2- thiones as antioxidants and antimicrobial agents

Balam Satheesh Krishna, Sanapa

Abstract

The present communication reveals the synthesis of novel (3aS)-2-substituted perhydro-2ë5-pyrrolo[1,2-c][1,3,2]oxazaphosphole-2-thiones, (6a-n). The synthetic pathway comprises two steps i.e., the synthesis of various (thio)phosphorodichlorides (5a-n) from thiophosphoryl chloride (3) and amino compounds (4a-l) and two drugs zidovudine (4m) and lamivudine (4n). They were further cyclized with (S)-(+)-prolinol (2) to yield the title compounds (6a-n). Here (S)-(+)-prolinol (2) is synthesized by the asymmetric reduction of S)-(+)-proline (1) with lithiumborohydride in the presence of trimethylsilyl chloride.All the newly synthesized compounds were characterized by spectral data, microanalyses and screened for their antioxidant and antimicrobial activity.Afew of them were found to possess significant antioxidant and antimicrobial activities.