Copyright (c) 2024 Rambabu Guguloth
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Docking and Biological Evaluation of New Series of Pyrrolidine Derivatives as Potent Antibacterial Agents
Corresponding Author(s) : Shiva Kumar Gubbiyappa
Asian Journal of Chemistry,
Vol. 36 No. 2 (2024): Vol 36 Issue 2, 2024
Abstract
The chemical flexibility of the pyrrolidine nucleus and its ability to generate a wide range of structural variations may have a significant impact on the therapeutic effectiveness. In present study, 17 analogs of 1-(4-bromo-2-(pyrrolidin-1-yl)benzyl)pyrrolidin-3-amine (7a-q) were synthesized and characterized. All the synthesized compounds were purified by combi-flash chromatography using RediSep RF 1.5 Flash silica gel columns. The synthesized compounds were investigated for antibacterial activity utilizing the agar well diffusion method. Apart from compounds 7l, 7o and 7p, antibacterial activity against E. coli was exhibited by almost all the compounds. All the tested compounds were effective in showing antibacterial activity against Bacillus and against Aspergillus niger, none of the drugs had antifungal efficacy. The SwissADME analysis of the synthesized compounds, the Lipinski characteristics revealed that compounds 7a, 7b, 7e-h, 7j-l, 7n and 7o don’t violate the rule of five. Therefore, these substances might be viewed as orally accessible and pharmacologically active drug candidates. Auto DockVina was used for the purpose of molecular docking of the synthesized compounds.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S. Poyraz, H.A. Döndas, N.Y. Döndas and J.M. Sansano, Front. Pharmacol., 14, 1239658 (2023); https://doi.org/10.3389/fphar.2023.1239658
- G. Li Petri, M.V. Raimondi, V. Spanò, R. Holl, P. Barraja and A. Montalbano, Top. Curr. Chem., 379, 34 (2021); https://doi.org/10.1007/s41061-021-00347-5
- A.A. Bhat, N. Tandon, I. Singh, R. Tandon, J. Mol. Struc., 1283, 135175 (2023); https://doi.org/10.1016/j.molstruc.2023.135175
- Y. Arun, G. Bhaskar, C. Balachandran, S. Ignacimuthu and P.T. Perumal, Bioorg. Med. Chem. Lett., 23, 1839 (2013); https://doi.org/10.1016/j.bmcl.2013.01.023
- M.S. Islam, A.M. Al-Majid, F.F. El-Senduny, F.A. Badria, A.F.M. Motiur Rahman, A. Barakat and Y.A.M.M. Elshaier, Appl. Sci., 10, 2170 (2020); https://doi.org/10.3390/app10062170
- D. Kowalczyk, J. Wojciechowski and L. Albrecht, Synthesis, 49, 880 (2017); https://doi.org/10.1055/s-0035-1562483
- A. Barakat, M.S. Islam, M. Ali, A.M. Al-Majid, S. Alshahrani, A.S. Alamary, S. Yousuf and M.I. Choudhary, Symmetry, 13, 1426 (2021); https://doi.org/10.3390/sym13081426
- H.-Y. Xiang, J.-Y. Chen, X.-J. Huan, Y. Chen, Z. Gao, J. Ding, Z.-H. Miao and C.-H. Yang, Bioorg. Med. Chem. Lett., 31, 127710 (2021); https://doi.org/10.1016/j.bmcl.2020.127710
- X. Liu, D. Lai, Q. Liu, L. Zhou, Q. Liu and Z. Liu, Molecules, 21, 1665 (2016); https://doi.org/10.3390/molecules21121665
- E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng and T.E. Ferrin, J. Comput. Chem., 25, 1605 (2004); https://doi.org/10.1002/jcc.20084
- O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
- C.A. Lipinski, Adv. Drug Deliv. Rev., 101, 34 (2016); https://doi.org/10.1016/j.addr.2016.04.029
- K. Tsaioun and S.A. Kates, ADMET for Medicinal Chemists: A Practical Guide, John Wiley & Sons (2011).
- S. Sekar, S. Pazhamalai, G. Ariharasivakumar and M. Gopalakrishnan, Der Pharma Chem., 9, 24 (2017).
References
S. Poyraz, H.A. Döndas, N.Y. Döndas and J.M. Sansano, Front. Pharmacol., 14, 1239658 (2023); https://doi.org/10.3389/fphar.2023.1239658
G. Li Petri, M.V. Raimondi, V. Spanò, R. Holl, P. Barraja and A. Montalbano, Top. Curr. Chem., 379, 34 (2021); https://doi.org/10.1007/s41061-021-00347-5
A.A. Bhat, N. Tandon, I. Singh, R. Tandon, J. Mol. Struc., 1283, 135175 (2023); https://doi.org/10.1016/j.molstruc.2023.135175
Y. Arun, G. Bhaskar, C. Balachandran, S. Ignacimuthu and P.T. Perumal, Bioorg. Med. Chem. Lett., 23, 1839 (2013); https://doi.org/10.1016/j.bmcl.2013.01.023
M.S. Islam, A.M. Al-Majid, F.F. El-Senduny, F.A. Badria, A.F.M. Motiur Rahman, A. Barakat and Y.A.M.M. Elshaier, Appl. Sci., 10, 2170 (2020); https://doi.org/10.3390/app10062170
D. Kowalczyk, J. Wojciechowski and L. Albrecht, Synthesis, 49, 880 (2017); https://doi.org/10.1055/s-0035-1562483
A. Barakat, M.S. Islam, M. Ali, A.M. Al-Majid, S. Alshahrani, A.S. Alamary, S. Yousuf and M.I. Choudhary, Symmetry, 13, 1426 (2021); https://doi.org/10.3390/sym13081426
H.-Y. Xiang, J.-Y. Chen, X.-J. Huan, Y. Chen, Z. Gao, J. Ding, Z.-H. Miao and C.-H. Yang, Bioorg. Med. Chem. Lett., 31, 127710 (2021); https://doi.org/10.1016/j.bmcl.2020.127710
X. Liu, D. Lai, Q. Liu, L. Zhou, Q. Liu and Z. Liu, Molecules, 21, 1665 (2016); https://doi.org/10.3390/molecules21121665
E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng and T.E. Ferrin, J. Comput. Chem., 25, 1605 (2004); https://doi.org/10.1002/jcc.20084
O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
C.A. Lipinski, Adv. Drug Deliv. Rev., 101, 34 (2016); https://doi.org/10.1016/j.addr.2016.04.029
K. Tsaioun and S.A. Kates, ADMET for Medicinal Chemists: A Practical Guide, John Wiley & Sons (2011).
S. Sekar, S. Pazhamalai, G. Ariharasivakumar and M. Gopalakrishnan, Der Pharma Chem., 9, 24 (2017).