Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4'-hydroxy-3'-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines

Mohammad Shaharyar; Anees Ahamed Siddiqui; Mohamed Ashraf Ali; Dharmarajan Sriram; Perumal Yogeeswari

doi:10.1016/j.bmcl.2006.05.024

Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4'-hydroxy-3'-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines

Bioorg Med Chem Lett. 2006 Aug 1;16(15):3947-9. doi: 10.1016/j.bmcl.2006.05.024. Epub 2006 May 24.

Authors

Mohammad Shaharyar¹, Anees Ahamed Siddiqui, Mohamed Ashraf Ali, Dharmarajan Sriram, Perumal Yogeeswari

Affiliation

¹ Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi-110062, India.

PMID: 16725324
DOI: 10.1016/j.bmcl.2006.05.024

Abstract

A series of N1-nicotinoyl-3- (4'-hydroxy-3'-methyl phenyl)-5-(substituted phenyl)-2-pyrazolines were synthesized by the reaction between isoniazid (INH) and chalcones and were tested for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv (MTB) and INH-resistant M. tuberculosis (INHR-MTB) using the agar dilution method. Among the synthesized compounds, compound (i) N1-nicotinyl-3-(4'-hydroxy-3'-methyl phenyl)-5-(1''-chlorophenyl)-2-pyrazoline was found to be the most active agent against MTB and INHR-MTB, with minimum inhibitory concentration of 0.26 microm. When compared to INH-compound i was found to be 2.8- and 43.7-fold more active against MTB and INHR-MTB, respectively.

MeSH terms

Animals
Antitubercular Agents / chemical synthesis*
Antitubercular Agents / pharmacology*
Chlorocebus aethiops
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Mycobacterium tuberculosis / drug effects*
Pyrazoles / chemical synthesis*
Pyrazoles / pharmacology*
Vero Cells

Substances

Antitubercular Agents
Pyrazoles