JOURNAL OF PHARMACOLOGY AND
BIOMEDICINE
ISSN.2456-8244
In the present work, cinnamic acid was modified to prepare 1,2,4-triazole-thiol analogs were synthesized and evaluated for an- ti-bacterial activity using disc diffusion/cup and plate method. Spectral analyses (IR and NMR) of the compounds satisfactorily supported the structures of the synthesized compounds. The FT- IR spectrum of compounds exhibited sharp peaks at 3200-2700 cm-1 (aliphatic C-H), 1400-1700 cm-1 (aromatic ring) and 2400- 2600 cm-1 (S-H str.), in all compounds while vibrations of NO2 (1300-1400 cm-1), C-Cl (850-550 cm-1) were also found in the cor- responding compounds. The 1H NMR spectra exhibit chemical shifts at ? 6.5-7.9 (aromatic protons), 1.25-2.56 (CH2) and 0.8 (CH3) and 8.0-8.4 (=CH) in corresponding compounds. The anti- bacterial activity of the synthesized compounds was evaluated at four different concentrations and the zone of inhibition was meas- ured against gram negative and gram positive bacteria. Only one compound (CT4) was found to contain a significant antibacterial action against the tested microorganisms. Also the action was bet- ter against gram positive bacteria in comparison to the gram nega- tive bacteria.
NAMES:
ONLINE ISSN:2456-8244
Keywords: Cinnamic acid , 1,2,4-triazole , antimicrobial , disc diffusion , synthesis
DOI:
1. Bansal RK. Heterocyclic Chemistry. 5th Ed. New Age Publishers, 2010.
2. Kaur P, Kaur R, Goswami M. A review on methods of synthesis of 1,2,4-triazole deriv-atives. International Research Journal of Pharmacy. 2018; 9(7): 1-35
3. Banerjee S, Ganguly S, Sen KK. A Review on 1, 2, 4 – Triazoles. Journal of Advanced Pharmacy Education & Research. 2013; 3(3): 102-115
4. Guzel E, C?evik UA, Evren AE, Bostanc? HE, Gu?l UD, Kay?s U, O?zkay Y, Kaplanc?kl? ZA. Synthesis of Benzimidazole-1,2,4-triazole Derivatives as Potential Antifungal Agents Targeting 14α-Demethylase. ACS Omega. 2023; 8: 4369-4384. Doi: 10.1021/acsomega.2c07755
5. Cai B-G, Li Q, Xuan J. Copper-catalyzed 2,3-dihydro-1,2,4-triazoles synthesis through [3þ2]-cycloaddition of nitrile ylides with azodicarboxylates. Green Synthesis and Ca-talysis. 2023. Article in Press. Doi: 10.1016/j.gresc.2023.01.007.
6. Cai B-G, Bao Y-P, Pei C, Li Q, Li L, Koenigs RM, Xuan J. Photochemical synthesis of 1,2,4-triazoles via addition reaction of tri-plet intermediates to diazoalkanes and azo-methine ylide intermediates. Chemical Science. 2022; 13: 13141. Doi: 10.1039/d2sc04720a.
7. Emami L, Sadeghian S, Mojaddami A, khabnadideh S, Sakhteman A, Sadeghpour H, Faghih Z, Fereidoonnezhad M, Rezaei Z. Design, synthesis and evaluation of novel 1,2,4-triazole derivatives as promising anti-cancer agents. BMC Chemistry. 2022; 16: 91. Doi: 10.1186/s13065-022-00887-x.
8. Zhou L-N, Feng F-F, Cheung CW, Ma J-A. Cu-Enabled [3 + 2] Annulation of In Situ Formed Nitrile Ylides with Aryldiazonium Salts: Access to 5-Cyano-1,2,4-Triazoles. Organic Letters. 2021; 23(3): 739–744. Doi: 10.1021/acs.orglett.0c03960
9. Kumari M, Tahlan S, Narasimhan B, Rama-samy K, Lim SM, Shah SAA, Mani V, Kakkar S. Synthesis and biological evaluation of heterocyclic 1,2,4-triazole scaffolds as promising pharmacological agents. BMC Chemistry. 2021; 15: 5. https://doi.org/10.1186/s13065-020-00717-y
10. El-Sayed R, Khairou KS. Propoxylated fatty thiazole, pyrazole, triazole, and pyrrole de-rivatives with antimicrobial and surface activity. Journal of Surfactants and Detergents. 2015; 18(4): 661–673.
11. El-Sayed R. Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives. Grasas Aceites. 2006; 57(2): 180188.
12. Mishra R, Mishra BJ, Hari Narayana Moor-thy NS. Synthesis and antimicrobial evaluation of some 3,4-dihydro pyrimidine-2-one derivatives. Trends in Applied Sciences Re-search. 2008; 3(2): 203-208.
13. Mishra R, Jain S. Investigation of antimi-crobial potential of some thiazolyl chalcone derivatives. PharmacologyOnline. 2013; 1: 190-193