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

Ersen D., Ulger M., MANGELINCKX S., Gemili M., ŞAHİN E., Nural Y.

MEDICINAL CHEMISTRY RESEARCH, cilt.26, sa.9, ss.2152-2160, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 26 Sayı: 9
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1007/s00044-017-1907-9
  • Dergi Adı: MEDICINAL CHEMISTRY RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2152-2160
  • Anahtar Kelimeler: 5, 5-Diphenylpyrrolidine, Thiohydantoin, Antibacterial activity, Antimycobacterial activity, M. tuberculosis H37Rv, 3+2 CYCLOADDITION REACTIONS, 1,3-DIPOLAR CYCLOADDITION, AZOMETHINE YLIDES, ASYMMETRIC 1,4-ADDITION, BIOLOGICAL EVALUATION, THIOUREA DERIVATIVES, CRYSTAL-STRUCTURE, COCAINE ABUSE, IN-VITRO, COMPLEXES
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.