Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues

Bioorganic & Medicinal Chemistry Letters
2011.0

Abstract

A series of novel isoniazid (INH) analogues were synthesized by microwave assisted one pot reaction of INH, various benzaldehydes and dimedone in water with catalytic amount of DBSA. The synthesized compounds were evaluated for their anti-TB activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant Mycobacterium tuberculosis (MDR-TB). Among the 29 compounds, compound N-[9-[2-(benzyloxy)phenyl]-3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-10(1H)-acridinyl]isonicotinamide (12) inhibited MTB with MIC of <0.17 μM and MDR-TB with MIC of 0.69 μM.

Knowledge Graph

Similar Paper

Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues
Bioorganic &amp; Medicinal Chemistry Letters 2011.0
Synthesis of isonicotinic acid N′-arylidene-N-[2-oxo-2-(4-aryl-piperazin-1-yl)-ethyl]-hydrazides as antituberculosis agents
Bioorganic &amp; Medicinal Chemistry Letters 2005.0
Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives
Bioorganic &amp; Medicinal Chemistry Letters 2012.0
Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones
Bioorganic &amp; Medicinal Chemistry Letters 2005.0
New series of isoniazid hydrazones linked with electron-withdrawing substituents
European Journal of Medicinal Chemistry 2011.0
Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines
Bioorganic &amp; Medicinal Chemistry Letters 2006.0
New one-pot synthesis of anti-tuberculosis compounds inspired on isoniazid
European Journal of Medicinal Chemistry 2020.0
Synthesis of highly potent novel anti-tubercular isoniazid analogues with preliminary pharmacokinetic evaluation
Bioorganic &amp; Medicinal Chemistry Letters 2012.0
Synthesis and anti-mycobacterial activity of (E)-N′-(monosubstituted-benzylidene)isonicotinohydrazide derivatives
European Journal of Medicinal Chemistry 2008.0
N-Hydroxythiosemicarbazones: Synthesis and in vitro antitubercular activity
Bioorganic &amp; Medicinal Chemistry Letters 2007.0