Synthesis, Characterization and Antimicrobial Evaluation of some 1,2,4-Triazolo-5-Thione Derivatives

Gurdeep Singh; Neetesh K. Jain; Kiran Sahu

doi:10.24092/CRPS.2021.110103

Gurdeep Singh School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab.
Neetesh K. Jain Oriental College of Pharmacy and Research, Oriental University, Indore (M.P.)
Kiran Sahu Oriental College of Pharmacy and Research, Oriental University, Indore (M.P.)

DOI https://doi.org/10.24092/CRPS.2021.110103

Abstract

Due to this increasing predicament of antibiotic confrontation, the lot of distinct antibiotics available is dwindling and there are only smatterings of new antibiotics in the drug development channel. Therefore, an intense necessitate for new antimicrobial drugs. In current study, substituted 1,2,4-triazolo-5-thione derivatives were synthesized from substituted aromatic aldehydes, succinic acids and the structure of synthesized compounds were established by physicochemical (Melting Point, Rf value) and spectral analysis (IR, NMR & Mass). The title compounds were then evaluated for their antimicrobial activity against ciprofloxacin as a standard drug using agar plate method. Among all synthesized derivatives A₅ and A₆ found were found to possess very promising antimicrobial activity.

Keywords: 1,2,4-triazolo-5-thione, anti-microbial, antibiotic, thione, Ciprofloxacin

References

1. Qun LI, Mitscher LA, Shen LL. The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med Res Rev. 2000; 20: 231–293.
2. Fassihi A, Abedi D, Saghaie L. Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxy-pyridine-4-one and 3-hydroxypyran-4-one derivatives. Eur J Med Chem. 2009; 44: 2145–2157.
3. Ragenovic KC, Vesna Dimova, Vlado Kakurinov, Molnar DG, Buzarovska A. Synthesis, antibacterial and antifungal activity of 4-substituted-5-aryl-1,2,4-triazole. Molecules 2001; 6: 815-824.
4. Holla BS, Poojary KN, Rao BS, Shivananda M. New bis amino mercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur J Med Chem. 2002 ; 37: 511–517.
5. Eswaran S, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur J Med Chem. 2009; 44: 4637–4647.
6. Zhang S, Gao C, Ren QC, Chang L, Feng LS. Triazole derivatives and their anti-tubercular activity. Eur J Med Chem. 2017; 138: 501–513.
7. Jin RY, Zeng CY, Liang XH, Sun XH, Liu YF, Wang YY, Zhou S. Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives. Bioorg Chem. 2018; 80: 253–260.
8. Wittine K, Babic MS, Makuc D, Plavec J, Pavelic S, Sedic M, Pavelic K, Leyssen P, Neyts J, Balzarini J, Mintas M. Novel 1,2,4-triazole and imidazole derivatives of l-ascorbic and imino-ascorbic acid: synthesis, anti-HCV and antitumor activity evaluations. Bioorg Med Chem. 2012; 20: 3675–3685.
9. Mathew V, Keshavayya J, Vaidya VP, Giles D. Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4- triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. Eur J Med Chem. 2007; 42: 823–840.
10. Shehry MF, Abu-Hashem AA, El-Telbani EM. Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur J Med Chem. 2010; 45: 1906–1911.
11. Zhang Q, Peng Y, Wang XI, Keenan SM, Arora S, Welsh WJ. Highly potent triazole-based tubulin polymerization inhibitors. J Med Chem. 2007; 50:749–754.