Design, Synthesis of New Imidazolium-1,2,3-triazole Hybrid Derivatives as Antimicrobial Agents

https://doi.org/10.22146/ijc.85704

Ameer Salem Muttaleb(1), Nardeen Adnan Berto(2), Sahar Adeeb Mamoori(3), Zaman Abdalhussein Ibadi Alaridhee(4), Ehab Kareem Obaid(5), Ali Jabbar Radhi(6*)

(1) Faculty of Agriculture, Al-Qasim Green University, Babylon 51001, Iraq
(2) Department of Engineering of Polymers and Petrochemicals Industries, University of Babylon, Babylon 51001, Iraq
(3) Faculty of Agriculture, Al-Qasim Green University, Babylon 51001, Iraq
(4) Department of Medical Laboratory Techniques, College of Health and Medical Techniques, University of Alkafeel, Najaf 54001, Iraq
(5) Faculty of Agriculture, Al-Qasim Green University, Babylon 51001, Iraq
(6) College of Pharmacy, University of Al-Kafeel, Najaf 54001, Iraq
(*) Corresponding Author

Abstract


New imidazolium salts with 1,2,3-triazole rings (rm1-rm5) were prepared in the current work using a design-driven synthetic procedure scheme. By using analytical techniques such as NMR, IR and spectral information, the chemical structures of target synthesized products were identified using results that were discovered in perfect accord with their assigned structures. The microorganism used in the current study were bacterial strains of Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Micrococcus luteus, as well as the fungal strains of Aspergillus niger and Candida albicans. All the end products were estimated for their antibacterial activity. The values for the minimum inhibitory concentration (MIC) were confirmed by comparison to the widely used antibiotics fluconazole and ciprofloxacin as control drugs. Particularly, the compounds (rm5) and (rm4) showed observable antibacterial activity. These compounds might offer a brand-new place to start when looking for new antibacterial medications.

Keywords


imidazole; 1,2,3-triazole ring; imidazolium salts; antifungal activity; antibacterial activity

Full Text:

Full Text PDF


References

[1] Xie, S., Xia, S., Xu, Z., Li, W., Wang, E., and Wang, S., 2021, An imidazole-based fluorescent probe for cupric ion, Synth. Met., 277, 116784.‏

[2] Jain, A.K., Ravichandran, V., Sisodiya, M., and Agrawal, R.K., 2010, Synthesis and antibacterial evaluation of 2–substituted–4,5–diphenyl–N–alkyl imidazole derivatives, Asian Pac. J. Trop. Med., 3 (6), 471–474.‏

[3] Yoneyama, H., and Katsumata, R., 2006, Antibiotic resistance in bacteria and its future for novel antibiotic development, Biosci., Biotechnol., Biochem., 70 (5), 1060–1075.

[4] Dheer, D., Singh, V., and Shankar, R., 2017, Medicinal attributes of 1,2,3-triazoles: Current developments, Bioorg. Chem., 71, 30–54.

[5] Nassar, E.M., Abdelrazek, F.M., Ayyad, R.R., and El-Farargy, A.F., 2016, Synthesis and some reactions of 1-aryl-4-acetyl-5-methyl-1,2,3-triazole derivatives with anticonvulsant activity, Mini-Rev. Med. Chem., 16 (11), 926–936.

[6] Rajasekaran, A., and Rajagopal, K.A., 2009, Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents, Acta Pharm., 59 (3), 355–364.

[7] Boechat, N., Ferreira, M.L.G., Pinheiro, L.C.S., Jesus, A.M.L., Leite, M.M.M., Júnior, C.C.S., Aguiar, A.C.C., de Andrade, I.M., and Krettli, A.U., 2014, New compounds hybrids 1H-1,2,3-triazole-quinoline against Plasmodium falciparum, Chem. Biol. Drug Des., 84 (3), 325–332.

[8] Shukla, J.D., Md Arif Ali, K., and Deo, K., 2015, Synthesis and pharmacological evaluation of novel 1-(2,6-difuorobenzyl)-1H-1,2,3-triazole derivatives for CNS depressant and anticonvulsant profile, Am. J. PharmTech Res., 5, 422–433.

[9] Zhang, S., Xu, Z., Gao, C., Ren, Q.C., Chang, L., Lv, Z.S., and Feng, L.S., 2017, Triazole derivatives and their anti-tubercular activity, Eur. J. Med. Chem., 138, 501–513.

[10] Dai, Z.C., Chen, Y.F., Zhang, M., Li, S.K., Yang, T.T., Shen, L., Wang, J.X., Qian, S.S., Zhu, H.L., and Ye, Y.H., 2015, Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives, Org. Biomol. Chem., 13 (2), 477–486.

[11] Jordão, A.K., Ferreira, V.F., Souza, T.M.L., de Souza Faria, G.G., Machado, V., Abrantes, J.L., de Souza, M.C.B.V., and Cunha, A.C., 2011, Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives, Bioorg. Med. Chem., 19 (6), 1860–1865.

[12] Faidallah, H.M., Girgis, A.S., Tiwari, A.D., Honkanadavar, H.H., Thomas, S.J., Samir, A., Kalmouch, A., Alamry, K.A., Khan, K.A., Ibrahim, T.S., AL-Mahmoudy, A.M.M., Asiri, A.M., and Panda, S.S., 2018, Synthesis, antibacterial properties and 2D-QSAR studies of quinolone-triazole conjugates, Eur. J. Med. Chem., 143, 1524–1534.

[13] Penthala, N.R., Madhukuri, L., Thakkar, S., Madadi, N.R., Lamture, G., Eof, R.L., and Crooks, P.A., 2015, Synthesis and anti-cancer screening of novel heterocyclic(2H)-1,2,3-triazoles as potential anti-cancer agents, Med. Chem. Commun., 6 (8), 1535–1543.

[14] Gregorić, T., Sedić, M., Grbčić, P., Tomljenović Paravić, A., Kraljević Pavelić, S., Cetina, M., Vianello, R., and Raić-Malić, S., 2017, Novel pyrimidine-2,4-dione–1,2,3-triazole and furo[2,3-d]pyrimidine2-one-1,2,3-triazole hybrids as potential anti-cancer agents: Synthesis, computational and X-ray analysis and biological evaluation, Eur. J. Med. Chem., 125, 1247–1267.

[15] Yan, X., Lv, Z., Wen, J., Zhao, S., and Xu, Z., 2018, Synthesis and in vitro evaluation of novel substituted isatin-propylene-1H-1,2,3-triazole-4-methylene-moxifoxacin hybrids for their anti-mycobacterial activities, Eur. J. Med. Chem., 143, 899–904.

[16] Chen, L., Zhao, B., Fan, Z., Liu, X., Wu, Q., Li, H., and Wang, H., 2018, Synthesis of novel 3,4-chloroisothiazole-based imidazoles as fungicides and evaluation of their mode of action, J. Agric. Food Chem., 66 (28), 7319–7327.‏

[17] Rossi, R., and Ciofalo, M., 2020, An updated review on the synthesis and antibacterial activity of molecular hybrids and conjugates bearing imidazole moiety, Molecules, 25 (21), 5133.‏

[18] Shamshina, J.L., Kelley, S.P., Gurau, G., and Rogers, R.D., 2015, Chemistry: Develop ionic liquid drugs, Nature, 528 (7581), 188–189.‏

[19] Miskiewicz, A., Ceranowicz, P., Szymczak, M., Bartuś, K., and Kowalczyk, P., 2018, The use of liquids ionic fluids as pharmaceutically active substances helpful in combating nosocomial infections induced by Klebsiella pneumoniae New Delhi strain, Acinetobacter baumannii and Enterococcus species, Int. J. Mol. Sci., 19 (9), 2779.‏

[20] Cuervo-Rodríguez, R., Muñoz-Bonilla, A., López-Fabal, F., and Fernández-García, M., 2020, Hemolytic and antimicrobial activities of a series of cationic amphiphilic copolymers comprised of same centered comonomers with thiazole moieties and polyethylene glycol derivatives, Polymers, 12 (4), 972.‏

[21] Becerril, R., Nerín, C., and Silva, F., 2020, Encapsulation systems for antimicrobial food packaging components: An update, Molecules, 25 (5), 1134.‏

[22] Wang, D., Richter, C., Rühling, A., Drücker, P., Siegmund, D., Metzler‐Nolte, N., Glorius, F., and Galla, H.J., 2015, A remarkably simple class of imidazolium‐based lipids and their biological properties, Chem. - Eur. J., 21 (43), 15123–15126.‏

[23] Voloshina, A.D., Gumerova, S.K., Sapunova, А.S., Kulik, N.V., Mirgorodskaya, A.B., Kotenko, A.A., Kotenko, A.A., Prokopyeva, T.M., Mikhailov, V.A., Zakharova, L.Y., and Sinyashin, O.G., 2020, The structure–activity correlation in the family of dicationic imidazolium surfactants: Antimicrobial properties and cytotoxic effect, Biochim. Biophys. Acta, Gen. Subj., 1864 (12), 129728.‏

[24] Kapitanov, I.V., Jordan, A., Karpichev, Y., Spulak, M., Perez, L., Kellett, A., Kümmerer, K., and Gathergood, N., 2019, Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series of L-phenylalanine-derived surface-active ionic liquids, Green Chem., 21 (7), 1777–1794.‏

[25] Mohsen, D.H., Radhi, A.J., Shaheed, D.Q., and Abbas, H.K., 2022, Synthesis new benzimidazole derivatives as antibacterial, J. Pharm. Negat. Results, 13 (3), 893–898.

[26] Radhi, A.J., Shaheed, D.Q., Heriz, M.H., and Oleiwi, Z.K., 2021, Preparation and study biological activity of polybarbiturate linked tetrazole ring, Res. J. Pharm. Technol., 14 (6), 3377–3379.‏

[27] Minoshima, M., Chou, J.C., Lefebvre, S., Bando, T., Shinohara, K.I., Gottesfeld, J.M., and Sugiyama, H., 2010, Potent activity against K562 cells by polyamide–seco-CBI conjugates targeting histone H4 genes, Bioorg. Med. Chem., 18 (1), 168–174.‏

[28] Mohamed, M.S., Kamel, M.M., Kassem, E.M., Abotaleb, N., Abd El-moez, S.I., and Ahmed, M.F., 2010, Novel 6,8-dibromo-4(3H)quinazolinone derivatives of anti-bacterial and anti-fungal activities, Eur. J. Med. Chem., 45 (8), 3311–3319.‏

[29] Daina, A., Michielin, O., and Zoete, V., 2017, SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Sci. Rep., 7 (1), 42717.

[30] Smith, D.A., 1994, Design of drugs through a consideration of drug metabolism and pharmacokinetics, Eur. J. Drug Metab. Pharmacokinet., 19 (3), 193–199.



DOI: https://doi.org/10.22146/ijc.85704

Article Metrics

Abstract views : 66 | views : 25


Copyright (c) 2024 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.