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Molecules 2015, 20(5), 8800-8815; doi:10.3390/molecules20058800

Design, Synthesis and Antitubercular Activity of Certain Nicotinic Acid Hydrazides

1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt
2
The Regional Center for Mycology and Biotechnology, Al-Azhar University, Cairo 11759, Egypt
3
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
4
Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 17 April 2015 / Revised: 12 May 2015 / Accepted: 12 May 2015 / Published: 15 May 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1105 KB, uploaded 15 May 2015]   |  

Abstract

Three series of 6-aryl-2-methylnicotinohydrazides 4ai, N′-arylidene-6-(4-bromophenyl)-2-methylnicotino hydrazides 7af, and N′-(un/substituted 2-oxoindolin-3-ylidene)-6-(4-fluorophenyl)-2-methylnicotinohydrazides 8ac were synthesized and evaluated for their potential in vitro antimycobacterial activity against M. tuberculosis. The results showed that isatin hydrazides 8ac are remarkably more active than the parent hydrazide 4c. Hydrazides 8b and 8c exhibited the highest activity among all the tested compounds (MIC = 12.5 and 6.25 µg/mL, respectively). Compounds 8b and 8c were also devoid of apparent cytotoxicity to HT-29, PC-3, A549, HepG2 and MCF-7 cancer cell lines. Besides, 8b and 8c showed good drug-likeness scores of 0.62 and 0.41, respectively. Those two isatin hydrazides could offer an excellent framework for future development to obtain more potent antitubercular agents. The SAR study suggested that lipophilicity of the synthesized derivatives is a crucial element that accounts for their antimycobacterial activity. Finally, a theoretical kinetic study was established to predict the ADME of the active derivatives. View Full-Text
Keywords: synthesis; nicotinic acid; hydrazides; antimycobacterial; ADME synthesis; nicotinic acid; hydrazides; antimycobacterial; ADME
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Eldehna, W.M.; Fares, M.; Abdel-Aziz, M.M.; Abdel-Aziz, H.A. Design, Synthesis and Antitubercular Activity of Certain Nicotinic Acid Hydrazides. Molecules 2015, 20, 8800-8815.

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