Anti-Tuberculosis Evaluation and Conformational Study of N-Acylhydrazones Containing the Thiophene Nucleus

dc.creatorCardoso, Laura Nogueira de Faria
dc.creatorBispo, Marcelle de Lima Ferreira
dc.creatorKaiser, Carlos Roland
dc.creatorWardell, James L.
dc.creatorWardell, Solange M. S. V.
dc.creatorLourenço, Maria Cristina da Silva
dc.creatorBezerra, Flávio A. F. M.
dc.creatorSoares, Rodrigo Pedro Pinto
dc.creatorRocha, Marcele Neves
dc.creatorSouza, Marcus Vinícius Nora de
dc.date2015-07-13T14:06:48Z
dc.date2015-07-13T14:06:48Z
dc.date2014
dc.date.accessioned2023-09-26T20:12:09Z
dc.date.available2023-09-26T20:12:09Z
dc.identifierCARDOSO, Laura Nogueira de Faria et al. Anti-Tuberculosis Evaluation and Conformational Study of N-Acylhydrazones Containing the Thiophene Nucleus. Archiv der Pharmazie / Chemistry in Life Sciences, v. 347, n. 6, p. 432-448, 2014.
dc.identifier0365-6233
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/11231
dc.identifier10.1002/ardp.201300417
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8851232
dc.descriptionA series of N-acylhydrazonyl-thienyl derivatives (compounds 2 and 3), mainly of the type 2-(aryl-CH=N-NHCOCH2 )-thiene (2: aryl = substituted-phenyl; 3: aryl = heteroaryl) were evaluated against Mycobacterium tuberculosis. Particularly active compound was 3 (heteroaryl = 5-nitrothien-2-yl or 5-nitrofuran-2-yl) with MIC values of 8.5 and 9.0 μM, respectively. Moderately active compounds were compound 3 (heteroaryl = pyridin-2-yl) and compound 2 containing aryl = 2- or 4-hydroxyphenyl groups, with MIC values between 170 and 408 μM. Compound 2 containing OMe, H, F, Cl, Br, CN, and NO2 substituents and compound 3 (heteroaryl = furan-2-yl, thien-2-yl, pyrrol-2-yl, imidazol-2-yl, pyridin-3-yl, and pyridin-4-yl) were all inactive. Clearly, there is no correlation of activity with the electronic effects of the substituents. The activities suggest different modes of biological action of the compounds having nitro-heteroaryl groups, on the one hand, and the 2-hydroxyphenyl or pyridin-2-yl substituents, on the other hand. Compounds having 2- or 4-hydroxyphenyl, 2-hydroxy-5-nitrophenyl, or 4-hydroxy-3-chlorophenyl were less cytotoxic than ethambutol. It is important to notice that compound 3 (aryl = 5-NO2 -furan-2-yl) exhibited a promising therapeutic index (TI = 1093.90), with a value 4.4 less than that of ethambutol. Compounds 2 and 3 exist in DMSO or MeOD solutions as mixtures of EC(O)N /EC=N and ZC(O)N /EC=N conformers.
dc.formatapplication/pdf
dc.languageeng
dc.publisherVerlag Chemie GmbH
dc.rightsrestricted access
dc.subjectAntimycobacterial activity
dc.subjectConformational study
dc.subjectN-Acylhydrazones
dc.subjectThiophene
dc.subjectTuberculosis
dc.titleAnti-Tuberculosis Evaluation and Conformational Study of N-Acylhydrazones Containing the Thiophene Nucleus
dc.typeArticle


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