A previous study was conducted on the synthesis and antibacterial evaluation of Mannich bases of 2-(thioalkyl)-1H-methylbenzimidazole derivatives. The results of this study showed that certain 2-(thioalkyl)-1H-methylbenzimidazole and 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl)benzimidazole derivatives possess antibacterial activities against clinical strains, such as Escherichia coli, Klebsiellapneumonia (Gram-negative bacteria), Staphylococcusaureus and Pseudomonas aeruginosa (Gram-positive bacteria). Following these favorable results, we extended the antibacterial evaluation of this series of molecules to environmental strains. The aim of this study was to assess the impact of the methyl-piperidine group fixed at position-1 of this new series of benzimidazoles on the antibacterial activity of environmental strains. In addition, we first evaluated the antibacterial activity of four 2-(thioalkyl)methylbenzimidazole derivatives and then that of five 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl) benzimidazole derivatives. This study allowed us to show that compounds 1d and 1e could inhibit bacterial growth in vitro of the Enterobacteria P1 strain with inhibition diameters of 17.3 ± 0.6 mm and 10 ± 0.0 mm, respectively. However, addition of methyl-piperidinyl in this series showed that five (5) of 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl) benzimidazole derivatives had an inhibitory effect on the in vitro growth of bacterial strains used except on Enterobacteria P2 with inhibition diameters between 10.0 ± 0.8 mm and 27.9 ± 1.4 mm. The introduction of the methyl-piperidinyl group at the 1-position of 2-(thioalkyl)-1H-methylbenzimidazole derivatives greatly improved the antibacterial activity against environmental bacteria such as Escherichia coli A1, A2, A3, and A4 and two Enterobacteria P1.
References
[1]
MOOC de l’Institut Pasteur (2021) Resistance to Antibacterial Agents. https://www.pasteur.fr/fr/centre-medical/fiches-maladies/resistance-aux-antibiotiques
[2]
ONU Info (2020) La résistance aux antimicrobiens est une réalité. https://news.un.org/fr/story/2020/11/1082572
[3]
Hamza, O. and Omran, R. (2022) Multidrug Drug Resistance of Escherichia coli and Klebsiella Isolated from Iraqi Patients and Microbiota. Journal of Biosciences and Medicines, 10, 240-252. https://doi.org/10.4236/jbm.2022.1011019
[4]
Shah, K., Chhabra, S., Shrivastava, S.K. and Mishra, P. (2013) Benzimidazole: A Promising Pharmacophore. Medicinal Chemistry Research, 22, 5077-5104. https://doi.org/10.1007/s00044-013-0476-9
[5]
Evrard, A., Siomenan, C., Etienne, C.T., Daouda, T., Souleymane, C., Drissa, S. and Ané, A. (2021) Design, Synthesis and in Vitro Antibacterial Activity of 2-Thiomethyl-benzimidazole Derivatives. Advances in Biological Chemistry, 11, 165-177. https://doi.org/10.4236/abc.2021.114012
[6]
Noolvi, M., Agrawal, S., Patel, H., Badiger, A., Gaba, M. and Zambre, A. (2014) Synthesis, Antimicrobial and Cytotoxic Activity of Novel Azetidine-2-One Derivatives of 1H-Benzimidazole. Arabian Journal of Chemistry, 7, 219-226. https://doi.org/10.1016/j.arabjc.2011.02.011
[7]
Luo, Y., Yao, J.P., Yang, L., Feng, C.L., Tang, W., Wang, G.F., Zuo, J.P. and Lu, W. (2010) Design and Synthesis of Novel Benzimidazole Derivatives as Inhibitors of Hepatitis B Virus. Bioorganic & Medicinal Chemistry, 18, 5048-5055. https://doi.org/10.1016/j.bmc.2010.05.076
[8]
Tonelli, M., Simone, M., Tasso, B., Novelli, F., Boido, V., Sparatore, F., et al. (2010) Antiviral Activity of Benzimidazole Derivatives. II. Antiviral Activity of 2-Phenylbenzimidazole Derivatives. Bioorganic & Medicinal Chemistry, 18, 2937-2953. https://doi.org/10.1016/j.bmc.2010.02.037
[9]
El Rashedy, A.A. and Aboul-Enein, H.Y. (2013) Benzimidazole Derivatives as Potential Anticancer Agents. Mini-Reviews in Medicinal Chemistry, 13, 399-407. https://doi.org/10.2174/1389557511313030008
[10]
Ramprasad, U., Nayak, N., Dalimba, U., Yogeeswari, P., Sriram, D., Peethambar, S.K., Achur, R. and Kumar, H.S.S. (2015) Synthesis and Biological Evaluation of New Imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole Derivatives. European Journal of Medicinal Chemistry, 95, 49-63. https://doi.org/10.1016/j.ejmech.2015.03.024
[11]
Wenzel, I.N., Wong, P.E., Maes, L., Muller, T.J.J., Siegel, R.L.K., Barrett, M.P. and Charvet, E.D. (2009) Unsaturated Mannich Bases Active against Multidrug-Resistant Trypanosoma brucei brucei Strains. ChemMedChem, 4, 339-351. https://doi.org/10.1002/cmdc.200800360
[12]
Patel, V.M., Patel, N.B., Chan-Bacab, M.J. and Rivera, G. (2018) Synthesis, Biological Evaluation and Molecular Dynamics Studies of 1,2,4-Triazole Clubbed Mannich Bases. Computational Biology and Chemistry, 76, 264-274. https://doi.org/10.1016/j.compbiolchem.2018.07.020
[13]
Al Nasr, I., et al. (2019) Antiparasitic Activities of New Lawsone Mannich Bases. Archiv der Pharmazie (Weinheim), 352, Article ID: 1900128. https://doi.org/10.1002/ardp.201900128
[14]
Taher, A.T., Khalil, N.A. and Ahmed, E.M. (2011) Synthesis of Novel Isatin-Thiazoline and Isatin-Benzimidazole Conjugates as Anti-Breast Cancer Agents. Archives of Pharmacal Research, 34, 1615-1621. https://doi.org/10.1007/s12272-011-1005-3
[15]
Vinoth Kumar, S., Subramanian, M.R. and Chinnaiyan, S.K. (2013) Synthesis, Characterisation and Evaluation of N-Mannich Bases of 2-Substituted Benzimidazole Derivatives. Journal of Young Pharmacists, 5, 154-159. https://doi.org/10.1016/j.jyp.2013.11.004
[16]
Jesudason, E.P., Sridhar, S.K., Malar, E.J.P., Shanmugapandiyan, P., Inayathullah, M., Arul, V., Selvaraj, D. and Jayakumar, R. (2009) Synthesis, Pharmacological Screening, Quantum Chemical and in Vitro Permeability Studies of N-Mannich Bases of Benzimidazoles through Bovine Cornea. European Journal of Medicinal Chemistry, 44, 2307-2312. https://doi.org/10.1016/j.ejmech.2008.03.043
[17]
Patel, V.M., Patel, N.B., Chan-Bacab, M.J. and Rivera, G. (2020) N-Mannich Bases of Benzimidazole as a Potent Antitubercular and Antiprotozoal Agents: Their Synthesis and Computational Studies. Synthetic Communications, 50, 858-878. https://doi.org/10.1080/00397911.2020.1725057
[18]
Coulibaly, S., Coulibali, S., Ablo, E., Coulibaly, B., Camara, T.E. and Adjou, A. (2022) Influence of N-methyl Piperidine on Antibacterial Activity of 2-(thioalkyl)-1H-methylbenzimidazole Derivatives. ChemXpress, 14, 1-11.
[19]
Dosso, M. and Aye-Kette, H. (2000) Contrôle de qualité de l’antibiogramme en pratique courante: Expérience du laboratoire de bactériologie de l’Institut Pasteur de Côte d’Ivoire. Bactériolo int, n spécial.
[20]
Koné, M. (2005) Potentiel des plantes médicinales de Côte-d’Ivoire dans le contrôle des haemonchoses chez les ovins. Thèse de Doctorat Unique en Biologie végétale, Spécialité: Phytochimie, Université de Cocody Abidjan, UFR Biosciences, Abidjan.
[21]
Ponce, A.G., Fritz, R., Del Valle, C. and Roura, S.I. (2003) Antimicrobial Activity of Essential Oils on the Native Microflora of Organic Swiss Chard. LWT—Food Science and Technology, 36, 679-684. https://doi.org/10.1016/S0023-6438(03)00088-4
[22]
Kouadio, N.J., Guessennd, N.K., Kone, M.W., Moussa, B., Koffi, Y.M., Guede, K.B., Yao, K., et al. (2015) Evaluation de l’activité des feuilles de Mallotus oppositifolius (Geisel.) Müll.-Arg (Euphorbiaceae) sur des bactéries multirésistantes et criblage phytochimique. International Journal of Biological and Chemical Sciences, 9, 1252-1262. https://doi.org/10.4314/ijbcs.v9i3.10
[23]
Fauchère, J. and Avril, J. (2002) Bactériologie générale et médicale. Ellipses.
[24]
Kamanzi, A. (2002) Plantes médicinales de Côte d’Ivoire: Investigations phytochimiques guidées par des essais biologiques. Doctorat d’Etat ès-Sciences en biologie végétale, UFR Biosciences, Université de Cocody, Abidjan.
