ONE-POT SYNTHESIS OF 2,4,5-TRIARYLIMIDAZOLES FROM KETO-OXIMES: CHARACTERIZATION AND EVALUATION OF ANTIMICROBIAL ACTIVITY

Authors

  • KRANTHI KUMAR T Department of Mewar University, Chittorgarh, Rajasthan, India.
  • SREENIVASULU R Department of Mewar University, Chittorgarh, Rajasthan, India.

DOI:

https://doi.org/10.22159/ajpcr.2019.v12i9.34741

Keywords:

Triarylimidazoles, Cyclization, Antibacterial, Antifungal, Antimycobacterial

Abstract

Background and Objective: Imidazole scaffold is pervasive in pharmaceuticals and it possesses diverse type of biological activities, especially triarylimidazole derivatives are biologically prominent molecules which inspired the current investigation. The objective of the work is to synthesize 15 novel 2,4,5-triarylimidazole derivatives and evaluate their antimicrobial and antimycobacterial activity against selected bacterial and fungal strains.

Methods: The title compounds 2,4,5-triaryl-imidazole were synthesized from the corresponding aryl aldehydes and keto-oximes through the cyclization to N-hydroxyimidazoles and reduced thermally to the different imidazole derivatives. Agar disc diffusion method is employed for the antimicrobial and antimycobacterial studies.

Results: Fifteen novel 2,4,5-triarylimidazoles were synthesized in adequate yields and characterization of the molecules was done by detailed spectral analysis using advanced analytical support. Results disclosed that all the synthesized compounds were exhibiting antimicrobial properties. Compounds 3h, 3g, 3b, and 3m were stated to possess potent antimicrobial properties in the given bacterial and fungal strains.

Conclusion: The current investigation results support the antimicrobial and antimycobacterial activity of the synthesized 2,4,5-triarylimidazole derivatives. Further, research is necessary to explore the mechanism involved in the antimicrobial activity.

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References

Sharma A, Kumar V, Kharb R, Kumar S, Sharma PC, Pathak DP, et al. Imidazole derivatives as potential therapeutic agents. Curr Pharm Des 2016;22:3265-301.

De Luca L. Naturally occurring and synthetic imidazoles: Their chemistry and their biological activities. Curr Med Chem 2006;13:1-23.

Nascimento MV, Munhoz AC, Theindl LC, Mohr ET, Saleh N, Parisotto EB, et al. A novel tetrasubstituted imidazole as a prototype for the development of anti-inflammatory drugs. Inflammation 2018;41:1334-48.

Grimmet MR. In: Katritzky AR, Rees CW, editors. Comprehensive Heterocyclic Chemistry. Vol. 5. NewYork: Pergamon; 1984. p. 457-532.

Li X, Chen X, Wang H, Chen C, Sun P, Mo B, et al. Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential heck and oxidative amination reaction. Org Biomol Chem 2019;17:4014-23.

Katritzky AR. Comprehensive Heterocyclic Chemistry. Exeter, UK: Pergamon; 1984. p. 469-98.

Norman SM, Bennett RD, Poling SM, Maier VP, Nelson MD. Paclobutrazol inhibits abscisic acid biosynthesis in Cercospora rosicola. Plant Physiol 1986;80:122-5.

Guven OO, Erdogan T, Goker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bio org Med Chem Lett 2007;17:2233-6.

Ayhan KG, Altanlar N. Synthesis and antifungal properties of some benzimidazole derivatives. Turk J Chem 2006;30:223-8.

Mukherjee A, Kumar S, Seth M, Bhaduri AP. Synthesis of 1-methyl- 4-nitro-5-substituted imidazole and substituted imidazolothiazole derivatives as possible antiparasitic agents. Indian J Chem 1989;28B:391-6.

Hadizadeh F, Hosseinzadeh H, Motamed-Shariaty VS, Seifi M, Kazemi S. Synthesis and antidepressant activity of N-substituted imidazole-5-carboxamides in forced swimming test model. Iran J Pharm Res 2008;7:29-33.

Singh P, Kumar R, Tiwari S, Khanna RS, Tewari AK. Docking, synthesis and evaluation of antioxidant activity of 2,4,5-triaryl imidazole. Clin Med Biochem Open Access 2015;1:105-11.

Tseng CH, Li CY, Chiu CC, Hu HT, Han CH, Chen YL, et al. Combretastatin A-4 derivatives: Synthesis and evaluation of 2,4,5-triaryl-1H-imidazoles as potential agents against H1299 (non-small cell lung cancer cell). Mol Divers 2012;16:697-709.

Barta TE, Stealey MA, Collins PW, Weier RM. Antiinflammatory 4,5-diarylimidazoles as selective cyclooxygenase inhibitors. Bioorg Med Chem Lett 1998;8:3443-8.

Breslin HJ, Cai C, Miskowski TA, Coutinho SV, Zhang SP, Hornby P, et al. Identification of potent phenyl imidazoles as opioid receptor agonists. Bioorg Med Chem Lett 2006;16:2505-8.

Yadav MR, Puntambekar DS, Sarathy KP, Vengurlekar S, Giridhar R. Quantitative structure activity relationships studies of diarylimidazoles as selective COX-2 inhibitors. Indian J Chem 2005;45B:475-82.

Wang G, Peng Z, Wang J, Li J, Li X. Synthesis and biological evaluation of novel 2,4,5-triarylimidazole–1,2,3-triazole derivatives via click chemistry as α-glucosidase inhibitors. Bioorg Med Chem Lett 2016;26:5719-23.

da Silva RB, Loback VB, Salomão K, de Castro SL, Wardell JL, Wardell SM, et al. Synthesis and trypanocidal activity of novel 2,4,5-triaryl-N-hydroxylimidazole derivatives. Molecules 2013;18:3445-57.

Runxia W, Chunsheng L, Genxiang L. A convenient synthesis of 2,4,5-triarylimidazoles catalyzed by Y(TFA)3. Green Chem Lett Rev 2010;3:101-4.

Jian FZ, Gui-Xia G, Xiao-Jun S, Yu-Lan Z. Facile method for one-step synthesis of 2,4,5-triarylimidazoles under catalyst-free, solvent-free, and microwave-irradiation conditions. Synth Commun 2010;40:1134-41.

Ericsson HM, Sherris JC. Antibiotic sensitivity testing. Report of an international collaborative study. Acta Pathol Microbiol Scand B Microbiol Immunol 1971;217:Suppl 217:1+.

lqahtani JM, Asaad AM. Anti-tuberculous drugs and susceptibility testing methods: Current knowledge and future challenges. J Mycobact Dis 2014;4:140-51.

Badrey MG, Gomha SM. Synthesis and antibacterial activity of fused isoxazole derivatives using grinding method. Int J Pharm Pharm Sci 2014;6:236-9.

Gomha SM. Efficient catalytic synthesis, characterization and antimicrobial evaluation of 1,4-bis(6-substituted-7-(2-aryl hydrazono)- 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl) benzene derivatives using chitosan. Int J Pharm Pharm Sci 2013;5:42-5.

Published

07-09-2019

How to Cite

KRANTHI KUMAR T, and SREENIVASULU R. “ONE-POT SYNTHESIS OF 2,4,5-TRIARYLIMIDAZOLES FROM KETO-OXIMES: CHARACTERIZATION AND EVALUATION OF ANTIMICROBIAL ACTIVITY”. Asian Journal of Pharmaceutical and Clinical Research, vol. 12, no. 9, Sept. 2019, pp. 263-70, doi:10.22159/ajpcr.2019.v12i9.34741.

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