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ynthesis, Characterization, and Comparative Study of Some Heterocyclic Compounds Containing Isoniazid and Nicotinic Acid Hydrazide Moieties M. Zalaa,*, J. J. Voraa, and H. B. Patelb a

Department of Chemistry, M. G. Science Institute, Gujarat University, Ahmedabad, Gujarat, 380009 India

b Department

of Chemistry, LJ Institute of Applied Sciences, Gujarat University, Ahmedabad, Gujarat, 380009 India *e-mail: [email protected]

Received May 25, 2020; revised June 10, 2020; accepted June 16, 2020

Abstract—Some new derivatives of six-membered heterocyclic compounds containing isoniazid and nicotinic acid hydrazide fragments have been synthesized according to green procedures with excellent yields. The structures of the synthesized compounds were confirmed by 1H and 13C NMR, IR, and mass spectra and elemental analyses. The compounds were screened for their in vitro antibacterial and antifungal activities. The results showed that the isoniazid derivatives are more active than their analogs containng a nicotinic hydrazide moiety. Keywords: isoniazid, nicotinic hydrazide, antimicrobial activity

DOI: 10.1134/S1070428020100218 INTRODUCTION Investigation of heterocyclic compounds is an interesting topic from both theoretical and practical points of view. There are a huge number of pharmacologically active heterocyclic compounds, many of which are in regular clinical use. Nitrogen heterocycles are most copious in nature than those containing oxygen or sulfur. Heterocyclic compounds are crucial to life in different ways. Most of sugars and their derivatives, including vitamins and some members of vitamin B group, have heterorings with a nitrogen atom. Analysis of the US FDA-approved drugs database shows that 59% of small-molecule drugs contain nitrogen heteroatom in a heterocycle [1]. Nitrogen-containing sixmembered heterocyclic compounds have acquired enormous significance in the field of drug discovery. In this work we report the synthesis and comparative study of antimicrobial activities of two types of sixmembered heterocyclic compounds derived from isoniazid and nicotinic acid hydrazide. Isoniazid is isonicotinic acid hydrazide which plays a vital role in the manufacture of various drugs such as anticancer, antitubercular, antifungal, antibacterial, and antiviral agents [2–5]. Nicotinic acid hydrazide which is iso-

meric to isoniazid has multiple applications and has long been known as biologically active compound. Pyridine derivatives have remarkable pharmaceutical importance because of their biological activity as antiHIV [6], antitubercular, antimicrobial [7], antidiabetic [8], anti-inflammatory [9], antiplasmodial [10], and anticancer [11] activities. Our goal was to synthesize and evaluate biological activity of some isoniazid and nicotinic acid hydrazide derivatives. RESULTS AND DISCUSSION In this study, new series of bipyrazole derivatives bearing isoniazid and nicotinic acid hydrazide moieties were synthesized as shown in Scheme 1. The starting compounds, 1H-pyrazole-4-carbaldehydes 4a and 4b were prep