SYNTHESIS, CHARACTERIZATION, AND EVALUATION OF ANTIFUNGAL PROPERTIES OF SUBSTITUTED BENZIMIDAZOLE ANALOG

  • Vijey Aanandhi M Department of Pharmaceutical Chemistry and Analysis, School of Pharmaceutical Sciences, Vels Institute of Science, Technology and Advanced Studies, Chennai, Tamil Nadu, India.
  • Anbhule Sachin J Department of Pharmaceutical Chemistry and Analysis, School of Pharmaceutical Sciences, Vels Institute of Science, Technology and Advanced Studies, Chennai, Tamil Nadu, India.

Abstract

Objective: The aim of the present study is to synthesize novel benzimidazole derivatives as potent antifungal agents.

Methods: 2-chloromethyl-1H-benzimidazole has been synthesized by refluxing o-phenylenediamine with chloroacetic acid in the presence of 5N HCL. Further, N-substituted benzimidazole derivatives containing various heteroamines and aromatic compounds were synthesized. These, finally, prepared derivatives were kept for in vitro antifungal property.

Results: A novel series of antifungal agents, containing benzimidazole nucleus as a basic skeleton, has been synthesized.

Conclusion: The synthesized novel benzimidazole derivatives exhibit moderate activity (VMSA 1, 2, 8), some compounds showed significant activity (VMSA 6, 9, and 10), and compound VMSA 4 and 5 exhibits maximum activity.

Keywords: Benzimidazole, In vitro, Significant, Antifungal activity, Aromatic.

References

1. Andriole VT. Effects of voriconazole on Candida glabrata in vitro. J Antimicrob Agents Chemother 1999;44:151-62.
2. Murray DK. Medical Microbiology. 2nd ed. New York: Wiley; 1990. p. 299-323.
3. Petrikkos G, Skiada A. Recent advances in antifungal chemotherapy. Int J Antimicrob Agents 2007;30:108-17.
4. Georgopapadakou NH, Walsh TJ. Human mycoses: Drugs and targets for emerging pathogens. Science 1994;264:371-3.
5. Perfect JR. Effects of mycorrhizal fungi on in vitro nitrogen response of some Dutch indigenous orchid species Can J Bot 1995;73:1187-91.
6. Groll AH, Delucca AJ. Walsh TJ. Kinase-phosphatase competition regulates Bacillus subtilis development. Trend Microbiol 1998;6:117-24.
7. Perfect JR. Antimicrob agents chemother in vitro characterization of azoles resistance in Candida albicans 1996;40:1577-83.
8. Balkovec JM. Section review: Anti-infectives: Lipopeptide antifungal agents. Exp Opin Invest Drugs 1994;3:65-82.
9. Fox JJ, Watanabe KA, Bloch A. Candida endocarditis and the impact of antifungal treatment on the corrected QT interval: A case report. Prog
Nucleic Acid Res Mol Biol 1966;7:251-313.
10. Bowman EJ, Siebers A, Altendorf K. Bafilomycins: A class of inhibitors of membrane ATP ases from microorganisms, animal cells, and plant cells. Proc Natl Acad Sci U S A 1988;85:7972-6.
11. Vincent TA. Risk of resistance related to antifungal use before admission in patients with community-acquired bacteraemia. J Antimicrob Chemother 1999;44:151.
12. Giulia M, Luisa, ME, Paola F, Silvia S, Angelo R, Lui C. Fungicidal activity of fluconazole against Candida albicans in a synthetic vagina-simulative medium. Bioorg Méd Chem 2004;12:5465.
13. Xiao L, Madison V, Chau AS, Loebenberg D, McNicholas PM. Antimicrobial susceptibility and synergy studies of Stenotrophomonas maltophilia isolates from patients with cystic fibrosis. J Antimicrob Chemother 2004;48:568.
14. Hunt ML, Cox AJ, Ruffolo CG, Rajakumar K, Adler B. Characterisation of a Pasteurella multocida esterase gene which confers a hemolytic phenotype in Escherichia coli under anaerobic conditions. FEMS Microbiol Lett 2000;192:249-56.
15. Potts KT. The chemistry of 1, 2, 4-triazoles. Chem Rev 1961;61:87.
16. Heeres J, Meerpoel L, Lewi P. Conazoles. Molecules 2010;15:4129-88.
17. Bruch HA, Smith WO. Nitrofuryl heterocycles. iii.1 3-alkyl-5-(5-nitro-2-furyl)-1, 2, 4-triazoles and intermediates. J Med Chem 1966;9:405.
18. Imperio D, Pirali T, Galli U, Pagliai F, Cafici L, Canonico PL, et al. Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry. Bioorg Med Chem 2007;15:6748-57.
19. Kucukguzel I, Kucukguzel GS, Rollas S, et al. II Farmaco. Med Chem 2004;59:893.
20. Shivarama Holla B, Veerendra B, Shivananda MK, Poojary B. Synthesis characterization and anticancer activity studies on some mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 2003;38:759-67.
21. Turan-Zitouni G, Sivaci M, Kiliç FS, Erol K. Synthesis of some triazolyl-antipyrine derivatives and investigation of analgesic activity. Eur J Med Chem 2001;36:685-9.
22. Hosur MS, Talwar R. Synthesis and antiinflammatory activity of 3-substituted-4-amino-5-mercapto-4(h)-1, 2, 4-triazole. Ind J Pharm Sci 1993;55:86.
23. Wade PC, Vogt BR, Kissick TP, Simpkins LM, Palmers DM. 1-Acyltriazoles as antiinflammatory agents. J Med Chem 1982;25:331.
24. Julino M, Stevens MF. Antitumour polycyclic acridines. Part 5.1 Synthesis of 7H-pyrido [4, 3, 2-kl] acridines with exploitable functionality in the pyridine ring. J Chem Soc Perkin Trans 1998;1:1677.
25. Passannanti A, Diana P, Barraja P, Lauria A, Montalbano A, Almerico AM. Antifungal compounds. Heterocycles 1998;48:1229.
26. Talwar MB, Laddi UV, Somannavar YS. Recent trends in antifungal agents and antifungal therapy. Indian J Heterocycl Chem 1995;4:297.
Statistics
43 Views | 25 Downloads
How to Cite
M, V. A., and A. S. J. “SYNTHESIS, CHARACTERIZATION, AND EVALUATION OF ANTIFUNGAL PROPERTIES OF SUBSTITUTED BENZIMIDAZOLE ANALOG”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 11, no. 16, Dec. 2018, pp. 66-69, doi:10.22159/ajpcr.2018.v11s4.31677.
Section
Original Article(s)