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

(2017) MEDICINAL CHEMISTRY RESEARCH. 26(9). p.2152-2160
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Abstract
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.
Keywords
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, 5, 5-Diphenylpyrrolidine, Thiohydantoin, Antibacterial activity, Antimycobacterial activity, M. tuberculosis H37Rv

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Chicago
Erşen, Duygu, Mahmut Ülger, Sven Mangelinckx, Müge Gemili, Ertan Şahin, and Yahya Nural. 2017. “Synthesis and Anti(myco)bacterial Activity of Novel 5,5-diphenylpyrrolidine N-aroylthiourea Derivatives and a Functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole.” Medicinal Chemistry Research 26 (9): 2152–2160.
APA
Erşen, D., Ülger, M., Mangelinckx, S., Gemili, M., Şahin, E., & Nural, Y. (2017). Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole. MEDICINAL CHEMISTRY RESEARCH, 26(9), 2152–2160.
Vancouver
1.
Erşen D, Ülger M, Mangelinckx S, Gemili M, Şahin E, Nural Y. Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole. MEDICINAL CHEMISTRY RESEARCH. 2017;26(9):2152–60.
MLA
Erşen, Duygu, Mahmut Ülger, Sven Mangelinckx, et al. “Synthesis and Anti(myco)bacterial Activity of Novel 5,5-diphenylpyrrolidine N-aroylthiourea Derivatives and a Functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole.” MEDICINAL CHEMISTRY RESEARCH 26.9 (2017): 2152–2160. Print.
@article{8546060,
  abstract     = {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.},
  author       = {Erşen, Duygu and Ülger, Mahmut and Mangelinckx, Sven and Gemili, Müge and Şahin, Ertan and Nural, Yahya},
  issn         = {1054-2523},
  journal      = {MEDICINAL CHEMISTRY RESEARCH},
  keywords     = {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,5,5-Diphenylpyrrolidine,Thiohydantoin,Antibacterial activity,Antimycobacterial activity,M. tuberculosis H37Rv},
  language     = {eng},
  number       = {9},
  pages        = {2152--2160},
  title        = {Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole},
  url          = {http://dx.doi.org/10.1007/s00044-017-1907-9},
  volume       = {26},
  year         = {2017},
}

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