ANTIMICROBIAL AND ANTHELMINTIC ACTIVITIES OF SOME NEWLY SYNTHESIZED TRIAZOLES
Objective: The objective of this work is to synthesize and evaluate some novel 1,2,4-triazoles.
Methods: Procedure includes synthesis of triazole compounds followed by biological evaluations. The synthesis was carried out in six steps withp-bromobenzoic acid as starting material and converting to ester and then to hydrazide. Hydrazide was then converted to 4-amino triazole. Theamino triazole was then linked to different secondary amines using chloroacetyl chloride as the linking agent. All the synthesized compounds werecharacterized through Fourier transform infrared spectroscopy, gas chromatography-mass spectroscopy, and nuclear magnetic resonance. Further,the compounds were taken out for biological evaluations. To explore their effects, experiments were conducted on various micro- as well as macroorganisms.The toxicityprofilewasalso testedin accordancewith OECD 425 guideline on Wistar albino rats.
Results: The compounds were examined for antibacterial as well as antifungal activities. Among the all compound T71, T73, and T75 exhibitedantibacterial activity, and compound T71 showed antifungal activity as well. The evaluation was also carried out for anthelmintic activities. Thecompounds were treated on Pheretima posthuma at various concentrations to explore their vermifuge and vermicidal action. The triazole linked with1-methylpiperazine was found to have comparable activity to that of reference standards.
Conclusion: Triazoles are a most potent assemblage of fungal retardants. But depending on their substituents, they also have diverse pharmacologicalvalues. In this study, the compound T71 showed promising antimicrobial as well as anthelmintic action. Hence, it can be considered as a lead compoundfor further researches.
2. Deb PK, Ghosh R, Das S, Bhakta T. In-vitro anthelmintic activity of Acorus calamis leaves. Asian J Pharm Clin Res 2013;6:135-7.
3. Dahiya SS, Solanki, P. Evaluation of in vitro anthelmintic activity of methanolic extract of different parts of Spermacoce articularis. Int J Pharm Pharm Sci 2011;3:244-7.
4. Webb EL, Mawa PA, Ndibazza J, Kizito D, Namatovu A, Kyosiimire-Lugemwa J, et al. Effect of single-dose anthelmintic treatment during pregnancy on an infantâ€™s response to immunisation and on susceptibility to infectious diseases in infancy: A randomised, double-blind, placebo-controlled trial. Lancet 2011;377(9759):52-62.
5. Darque A, DumÃ¨tre A, Hutter S, Casano G, Robin M, Pannecouque C, et al. Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates. Bioorg Med Chem Lett 2009;19(20):5962-4.
6. Antus S, GulÃ¡csi K, JuhÃ¡sz L, Kiss L, KurtÃ¡n T. Synthesis of naturally occurring o-heterocyclic compounds of biological activity. Pure Appl Chem 2004;76:1025-32.
7. Martin RJ. Modes of action of anthelmintic drugs. Vet J 1997;154:11-34.
8. Singhal N, Sharma PK, Dudhe R, Kumar N. Recent advancement of triazole derivatives and their biological significance. J Chem Pharm Res 2011;3:126-33.
9. Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, et al. Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review. J Pharm Bioallied Sci 2011;3(2):194-212.
10. Ahmadi F, Ghayahbashi MR, Sharifzadeh M, Alipoiur E, Ostad SN, Vosooghi M, et al. Synthesis and evaluation of anti-inflammatory and analgesic activities of new 1,2,4-triazole derivatives. Med Chem 2014;11(1):69-76.
11. Li X, Li XQ, Liu HM, Zhou XZ, Shao ZH. Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing ?-butenolide moiety. Org Med Chem Lett 2012;2(1):26.
12. Somorai T, SzilÃ¡gyi G, Reiter J, PongÃ³ L, LÃ¡ng T, Toldy L, et al. New acylated 1,2,4-triazoles as antiviral agents. Arch Pharm (Weinheim) 1986;319(3):238-42.
13. Chernyshev VM, Chernysheva AV, Taranushich VA. Synthesis of esters and amides of 5-amino-1,2,4-triazole-3-carboxylic and 5-amino-1,2,4-triazol-3-ylacetic acids. Russ J Appl Chem 2006;79:783-6.
14. Almasirad A, Mousavi Z, Tajik M, Assarzadeh MJ, Shafiee A. Synthesis, analgesic and anti-inflammatory activities of new methyl-imidazolyl-1,3,4-oxadiazoles and 1,2,4-triazoles. Daru 2014;22(1):22.
15. Upmanyu N, Gupta JK, Shah K, Mishra P. Anti-inflammatory and antinociceptive evaluation of newly synthesized 4-(substituted ethanoyl) amino-3-mercapto-5-(4-methoxy) phenyl-1,2,4-triazoles. J Pharm Bioallied Sci 2011;3(2):259-65.
16. Majumder S, Maya Bashyal B, Gupta RL. Synthesis of Schiff bases of 4-amino-3-mercapto-5-pyridin-4yl-4H-1,2,4-triazole and their evaluation as SAR inducers. Indian J Chem 2015;54:1260-74.
17. Upmanyu N, Kumar S, Shah K, Mishra P. Synthesis and antimicrobial studies of some 4-(Substituted)-ethanoylamino-3-mercapto-5- (4-Substituted) phenyl-1,2,4-triazoles. Dhaka Univ J Pharm Sci 2012;11:7-18.
18. Upmanyu N, Kumar S, Porwal P, Shah K, Mishra P. Synthesis and evaluation of 4-(substituted)-acetylamino-3-mercapto-5-(4-substituted) phenyl-1,2,4-triazole derivatives as antimicrobial agents. Med Chem Res 2012;21:1967-76.
19. Upmanyu N, Gupta JK, Shah K, Mishra P. Synthesis of new 1,2,4-triazoles as anti-inflammatory and anti-nociceptive agents. Pharm Chem J 2011;45:433-9.
20. Mondal P, Jana S, Balaji A, Ramakrishna R, Kanthal L. Synthesis of some new isoxazoline derivatives of chalconised indoline 2-one as a potential analgesic, antibacterial and anthelmimtic agents. J Young Pharm 2012;4:38-41.
21. Das SS, Dey M, Ghosh AK. Determination of anthelmintic activity of the leaf and bark extract of Tamarindus indica linn. Indian J Pharm Sci 2011;73:104-7.
22. Mohandas S, Sreekumar TR, Prakash V. Anthelmintic activity of Vidangadi Curna. Asian J Pharm Clin Res 2013;6:94-5.
23. Matar SA, Talib WH, Mustafa MS, Mubarak MS, AlDamen MA. Synthesis, characterization, and antimicrobial activity of Schiff bases derived from benzaldehydes and 3,3â€²-diaminodipropylamine. Arab J Chem 2015;8:850-7.
24. Paredes D, Ortiz C, Torres R. Synthesis, characterization, and evaluation of antibacterial effect of Ag nanoparticles against Escherichia coli O157:H7 and methicillin-resistant Staphylococcus aureus (MRSA). Int J Nanomed 2014;9:1717-29.
25. Hussain A, Zaman MK, Ramteke M. Antibacterial activity of trunk bark of Alstonia scholaris. Asian J Pharm Clin Res 2010;3:46-7.
26. Wiegand I, Hilpert K, Hancock RE. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc 2008;3:163-75.
27. Chandrappa SM, Gowda TS. Antibacterial activity of Coleus aromaticus leaves. Int J Pharm Pharm Sci 2010;2:63-6.
28. Shakhatreh MA, Al-Smadi ML, Khabour OF, Shuaibu FA, Hussein EI, Alzoubi KH. Study of the antibacterial and antifungal activities of synthetic benzyl bromides, ketones, and corresponding chalcone derivatives. Drug Des Devel Ther 2016;10:3653-60.
29. Bhalodia NR, Shukla VJ. Antibacterial and antifungal activities from leaf extracts of Cassia fistula l.: An ethnomedicinal plant. J Adv Pharm Technol Res 2011;2:104-9.
30. Khor ES, Wong KV. Comparison study of therapeutic properties of proteins and secondary metabolites from Carica papaya. Int J Pharm Pharm Sci 2016;8:153-8.
31. RodrÃguez-Tudela JL, Barchiesi F, Bille J, Chryssanthou E, Cuenca-Estrella M, Denning D, et al. Method for the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts. Clin Microbiol Infect 2003;9:iâ€“viii.
32. Ahmad F, Tabassum N. Preliminary phytochemical, acute oral toxicity and antihepatotoxic study of roots of Paeonia officinalis Linn. Asian Pac J Trop Biomed 2013;3:64-8.
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.