Antitubercular and Antimicrobial Activity of NH4VO3 Promoted 1,4- Dihydropyridine Incorporated 1,3,4-trisubstituted Pyrazole

Author(s): Nandam Harikrishna, Arun M. Isloor*, K. Ananda, Tanya Parish, Joazaizulfazli Jamalis, Hazem A. Ghabbour, Hoong-Kun Fun

Journal Name: Letters in Drug Design & Discovery

Volume 14 , Issue 6 , 2017

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Graphical Abstract:


Background: A new series of pyrazole containing 1,4-dihydropyridine derivatives 5a-i and 6a-i were synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction.

Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate (NH4VO3). The role of ammonium metavanadate was increases rate of the reaction and obtained high yields.

Result: Structures of newly synthesized 1,4-dihydropyridine moiety containing pyrazole derivatives were confirmed by FT-IR, NMR and Mass spectral studies. The structure of compound 5b was confirmed by S-XRD study. Further, these compounds were tested for in-vitro antitubercular and antimicrobial studies. Compounds 5a, 5b, 5i, 6a, 6b, 6g, 6h, and 6i were found to be active against all the bacterial microorganisms.

Conclusion: The above mentioned compounds have shown lowest MIC ranging between 3.12-12.5 μg/ml against Mycobacterium tuberculosis and MIC values ranging between 7.8- 15.6 μg/ml for Mycobacterium smegmatis, Staphylococcus aureus and Pseudomonas aeruginosa. For the control of life threatening diseases such as tuberculosis, these eight compounds may be strongly promising synthetic compounds.

Keywords: 1, 3, 4-Trisubstituted pyrazole, 1, 4-dihydropyridine, multistep reaction, ammonium metavanadate, antitubercular study, antimicrobial studies.

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Article Details

Year: 2017
Page: [699 - 711]
Pages: 13
DOI: 10.2174/1570180813666161103145224
Price: $65

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