Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles

A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1-isonicotinoyl-4,5-dihydropyrazoles (2a-i) were synthesised by the cyclocondensation reaction of 4-methoxy-1,1,1-trifluoro[chloro]-4-(substituted)-alk-3-en-2-ones (1a-i) and isoniazid (INH). Their in vitro antimicrobial activity was t...

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Published in	International journal of antimicrobial agents Vol. 32; no. 2; pp. 139 - 144
Main Authors	Almeida da Silva, Pedro E, Ramos, Daniela F, Bonacorso, Helio G, de la Iglesia, Agustina I, Oliveira, Marli R, Coelho, Tatiane, Navarini, Jussara, Morbidoni, Hector R, Zanatta, Nilo, Martins, Marcos A P
Format	Journal Article
Language	English
Published	Netherlands 01.08.2008
Subjects	Antitubercular Agents - chemical synthesis Antitubercular Agents - pharmacology Drug Resistance, Bacterial Humans Isoniazid - chemistry Isoniazid - pharmacology Microbial Sensitivity Tests Mycobacterium - drug effects Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Pyrazoles - chemical synthesis Pyrazoles - pharmacology
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Abstract	A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1-isonicotinoyl-4,5-dihydropyrazoles (2a-i) were synthesised by the cyclocondensation reaction of 4-methoxy-1,1,1-trifluoro[chloro]-4-(substituted)-alk-3-en-2-ones (1a-i) and isoniazid (INH). Their in vitro antimicrobial activity was tested against INH-susceptible Mycobacterium tuberculosis H37Rv, INH-resistant clinical M. tuberculosis isolates and non-tuberculous mycobacteria. Amongst the synthesised compounds, 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)-pyrazole (2a) and 5-hydroxy-3-(4-methylphenyl)-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazole (2d) were found to be the two most active agents against susceptible M. tuberculosis and several INH-resistant strains. The compound 3-(2-furyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)pyrazole (2f) was active against all the INH-resistant strains regardless of the genetic background at concentrations two- to four-fold its minimum inhibitory concentration against M. tuberculosis H37Rv. These compounds were inhibitors of mycolic acid biosynthesis, in agreement with the utilisation of the INH scaffold for their design. Interestingly, the most active compound against M. tuberculosis, 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)-pyrazole (2a), was even more potent than INH against non-tuberculous mycobacteria.
AbstractList	A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1- isonicotinoyl-4,5-dihydropyrazoles ( 2a- i) were synthesised by the cyclocondensation reaction of 4-methoxy-1,1,1-trifluoro[chloro]-4- (substituted)-alk-3-en-2-ones ( 1a- i) and isoniazid (INH). Their in vitro antimicrobial activity was tested against INH-susceptible Mycobacterium tuberculosis H37Rv, INH-resistant clinical M. tuberculosis isolates and non-tuberculous mycobacteria. Amongst the synthesised compounds, 5-hydroxy-5- trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)-pyrazole ( 2a) and 5- hydroxy-3-(4-methylphenyl)-5-trifluoromethyl-4,5-dihydro-1H-1- (isonicotinoyl) pyrazole ( 2d) were found to be the two most active agents against susceptible M. tuberculosis and several INH-resistant strains. The compound 3-(2-furyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- (isonicotinoyl)pyrazole ( 2f) was active against all the INH-resistant strains regardless of the genetic background at concentrations two- to four- fold its minimum inhibitory concentration against M. tuberculosis H37Rv. These compounds were inhibitors of mycolic acid biosynthesis, in agreement with the utilisation of the INH scaffold for their design. Interestingly, the most active compound against M. tuberculosis, 5-hydroxy-5- trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)-pyrazole ( 2a), was even more potent than INH against non-tuberculous mycobacteria.
Author	Coelho, Tatiane Ramos, Daniela F de la Iglesia, Agustina I Navarini, Jussara Zanatta, Nilo Almeida da Silva, Pedro E Bonacorso, Helio G Morbidoni, Hector R Oliveira, Marli R Martins, Marcos A P
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Snippet	A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1-isonicotinoyl-4,5-dihydropyrazoles (2a-i) were synthesised by the cyclocondensation reaction... A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1- isonicotinoyl-4,5-dihydropyrazoles ( 2a- i) were synthesised by the cyclocondensation...
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SubjectTerms	Antitubercular Agents - chemical synthesis Antitubercular Agents - pharmacology Drug Resistance, Bacterial Humans Isoniazid - chemistry Isoniazid - pharmacology Microbial Sensitivity Tests Mycobacterium - drug effects Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Pyrazoles - chemical synthesis Pyrazoles - pharmacology
Title	Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles
URI	https://www.ncbi.nlm.nih.gov/pubmed/18571384 https://search.proquest.com/docview/19652402 https://search.proquest.com/docview/69299922
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