SYNTHESIS, CHARACTERIZATION, AND ANTIMICROBIAL EVALUATION OF 3,5-DISUBSTITUTED TRIAZOLES BEARING 5-CHLORO-2-METHYLINDOLE: SYNTHESIS OF NOVEL 1,2,4- TRIAZOLES

SABA SHIREEN; BHARATH RATHNA KUMAR P

doi:10.22159/ajpcr.2019.v12i10.35004

Authors

SABA SHIREEN Department of Pharmaceutical Chemistry, Anwarul Uloom College of Pharmacy, Hyderabad, Telangana, India,
BHARATH RATHNA KUMAR P Department of Pharmaceutical Chemistry, Anwarul Uloom College of Pharmacy, Hyderabad, Telangana, India,

DOI:

https://doi.org/10.22159/ajpcr.2019.v12i10.35004

Keywords:

1,2,4-Triazole, Indole, Antibacterial activity, Antifungal activity

Abstract

Objectives: Synthesis, characterization, and antimicrobial evaluation of some novel 1,2,4-triazole derivatives clubbed with indole.

Methods: Procedure includes the synthesis of 1,2,4-triazole compounds by condensation reaction with ammonia. The synthesis was carried out in three steps with chlorophenylhydrazine hydrochloride as starting material with ethyl acetoacetate and hydrazine hydrate in the presence of ethanol to form hydrazide derivative. The hydrazide derivative then refluxed with ammonium acetate to get the desired compounds.

Results: All the synthesized compounds were characterized and confirmed by Fourier-transform infrared spectroscopy, mass spectroscopy, and nuclear magnetic resonance spectroscopy. The new compounds (Va-f) synthesized were evaluated for antimicrobial activity.

Conclusion: All the compounds Va-f screened for antimicrobial activity against selected strains of microorganisms. Compound Vb was found to be potent against Escherichia coli, Vc was found to be more active against Aspergillus niger.

Downloads

Download data is not yet available.

References

Shahid S, Naziabegum S, Zamir MD, Salunke SD and Baseer MA. Synthesis of new 2-substituted phenyl-1H-indole reaction. Chem Sci Trans 2013;2:584-8.

Nagaraju G, Sai KB, Saimeghana M, Chandana K, Ramarao N. Synthesis, Characteriztion and biological activity of indole-2-carboxylic acid derivatives. Int J Pharm Chem 2015;5:201-6.

Imtiyaz AK, Firdous GK, Minhaaj R. Synthesis, characterization and antimicrobial evaluation of some new N-(2,4-di chloloro benzyl)- indolylchalcones. J Chem Pharm Res 2013;5:631-6.

Sharma V, Kumar P, Pathak D. Biological importance of the indole nucleus in recent years: A comprehensive review. J Heterocycl Chem 2010;47:491-502.

Narayana B, Ashalatha BV, Vijaya Raj KK, Fernandes J, Sarojini BK. Synthesis of some new biologically active 1,3,4-oxadiazolyl nitroindoles and a modified fischer indole synthesis of ethyl nitro indole-2- carboxylates. Bioorg Med Chem 2005;13:4638-44.

Saravanan B, Akhilesh U, Bhaskar A, Manivannan V. Synthesis and molecular docking studies of diethyl 2-{[3-(2,4,6-trimetjhylbenzyl- 1-phenyl sulfonyl-1H-indol-2-yl]methyidene} propanedioate against hypertensive protein as a potential target. Asian J Pharm Clin Res 2013;6:172-4.

Saravanan B, Akhilesh U, Bhaskar A, Manivannan V. Synthesis, characterization and biological evaluation of indole derivatives bearing Benzimidazole benzothiazole moiety. Int J Pharm Pharm Sci 2017;9:128-38.

Mashayekhi V, Haj Mohammad Ebrahim Tehrani K, Azerang P, Sardari S, Kobarfard F. Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones. Arch Pharm Res 2013. https://doi.org/10.1007/s12272-013-0242-z.

Doddappa PA, Biradar JS. Synthesis characterization and antimicrobial activities of 2-(5-subsituted 3-phenyl-1H-indole-2-yl)-5-subsituted- 7H-[1,3,4] oxadiazolo/thidiazolo[3,2-a][1,3,5] triazine-7-thiaones. J Chem Pharm Res 2013;5:75-85.

Kumar A, Sing CP. Synthesis, characterization and biological activity of some new sulpha/substituted phenylazo indoles. Int J Sci Res 2015;4:934-8.

Swami PV, Kumar VK, Reddy RV, Anindita C. Microwave assisted synthesis, characterization and biological evaluation of phenyl acrylamide derivatives of triazoles derived from oxazolones. Asian J Pharm Clin Res 2018;11:285-90.

El-Sayed WA, Eman MF, Eman MH. Anticancer and antimicrobial activities of some synthesized pyrazle and triazole derivatives. J Pharm Chem 2012;4:23-32.

Pradeep KG, Bhandari A, Rana AC. Synthesis of some 3-Substituted- 4H-1, 2, 4-triazole derivatives with potent anti-inflammatory activity. Asian J Pharm Clin Res 2010;3:244-6.

Sudhir NS, Suhas AP. Synthesis of 3-substituted-4-amino-5-mercapto- 4(H)-1, 2, 4- triazole and screening for anti-convulsant activity. Int J Res Pharm Bio Sci 2011;2:520-4.

Khanage S, Popat BM, Ramdas BP, Raju S. Study of analgesic activity of novel 1,2,4-triazole derivatives bearing pyrazole and tetrazole moiety. J Pharm Res 2011;4:609-11.

Kumar PD, Singh V, Deepak PD, Kumar MR. Synthesis, characterization and antimicrobial evaluation of some 1, 2, 4-triazole derivatives. Int J Pharm Sci Res 2014;6:213-6.

Dasan N, Babu G, George S. Molecular docking studies and synthesis of 3,4-disubstituted triazoles as mycobacterium tuberculosis enoyl-ACP reductase and CYP-51 inhibitors. Int J Pharm Pharm Sci 2019;11:85-91.

Kumari M, Narang R, Naik SK, Singh SK, Gupta V, Balasubramanian N. Synthesis, molecular modeling and quantitative structure activity relationship studies of undec-10-enehydrazide derivatives as antimicrobial agents. Asian J Pharm Clin Res 2017;10:94-105.

Kumar PB, Subramaniyan S, Yamini K, Suthakaran R. Synthesis of some novel-1H-pyrazole derivatives and their antibacterial activity studies. Rasayan J Chem 2011;4:400-4.

Singh DV, Ram MA, Mani MR. Synthesis and characterization of some antifungal pyrimidinone derivatives. Indian J Heterocycl Chem 2004;14:43-6.

Black JG. Microbiology Principles and Exploration. 4th ed. New Delhi: Prentice-Hall; 1991. p. 163.

Goto S, Jo K, Kawakita T, Mitsuhashi S, Nishino T, Ohsawa N, et al. Determination method of minimum inhibitory concentrations. Chemother 1981;29:76-9.