Synthesis of Alkylated Pyrrolidine Epoxides from Amino Alcohol Derived Substrates and Study of their Antibacterial and Antifungal Activities

Abstract

This research work is focused to design novel antibiotic compound because over time, bacterial strains became resistant to the antibiotics used to treat infections. The -NH₂ group in amino alcohol is protected with diphenylphosphonic chloride (-dpp) in the presence of (Et)₃N. The dppamino-2-propanol was treated with N-methyl morpholine-N-oxide, tetrapropylammonium perruthenate in anhydrous CH₂Cl₂ at room temperature and –dpp amino ketone was obtained. An alkylated pyrrolidine epoxide was synthesized by treating –dpp amino ketone with diphenylbromo ethyl sulfonium salt in the presence of 1,8-diazabicyclo [5.4.0] undec-7-ene at 0 oC. The products were purified by flash chromatography and characterized by spectroscopic techniques. The antibacterial activity of intermediates and cyclic compound was checked through well diffusion method. The in vitro antifungal activity of intermediates and synthesized compound was evaluated
against three human pathogenic fungi.