Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole

In this paper, five novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives were synthesized by stereoselective cycloaddition of N-diphenylmethylene-protected glycine methyl ester and methyl acrylate, and subsequent coupling with aroylisothiocyanates. The cis-stereochemistry of one of the heterocyclic thiourea derivatives was characterized by single crystal X-ray diffraction studies. The compounds showed antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Aeromonas hydrophila, Escherichia. coli and Acinetobacter baumannii with minimum inhibitory concentration values in the range of 62.5-1000 mu g/mL against these bacterial strains. Antimycobacterial activity of the compounds was investigated against the M. tuberculosis H37Rv strain and all compounds exhibited antimycobacterial activity with a minimum inhibitory concentration value of 80 mu g/mL. Additionally, methyl 5,5-diphenylhexahydro-1-oxo-3thioxo- H-1-pyrrolo[1,2-c] imidazole-6-carboxylate was synthesized by cyclization reaction of the 5,5-diphenylpyrrolidine N-aroylthiourea derivatives in the presence of hydrazine monohydrate and exhibited antibacterial activity with a minimum inhibitory concentration value of 62.5 mu g/mL against the same bacterial strains and exhibited antimycobacterial activity with a minimum inhibitory concentration value of 80 mu g/mL against the M. tuberculosis H37Rv strain.