Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/32290
Title: Synthesis, potent anti-TB activity against M. tuberculosis ATTC 27294, crystal structures and complex formation of selected 2-arylidenehydrazinylbenzothiazole derivatives
Authors: Pinheiro, Alessandra C.
Souza, Marcus V. N. de
Lourenço, Maria C. S.
Costa, Cristiane F. da
Baddeley, Thomas C.
Low, John N.
Wardell, Solange M. S. V.
Wardell, James L.
Affilliation: Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Departamento de Bacteriologia. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.
University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK.
University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK.
CHEMSOL. Aberdeen, Scotland, UK.
Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil / University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK.
Abstract: The synthesis, anti-TB activity, crystal structures and ligand ability of a number of 2-arylidene-benzylidenehydrazinylbenzothiazole derivatives, 1, have been investigated. The compounds 1 were obtained from 2-hydrazinobenzothiazole and substituted benzaldehydes in refluxing methanol in yields, after recrystallisation, of 55e75%. The crystal structure determination of compounds, 1e (aryl ¼ 4-MeOC6H4), 1h (aryl ¼ pyridin-2-yl), 1f (aryl ¼ 2-HO-5-MeC6H3) revealed amino forms, whereas an imino form was found for 1f (aryl ¼ 2-HO-4-MeOC6H3). Despite the different tautomeric forms of 1e and 1h, the two compounds have similar cell dimensions and furthermore their intermolecular interactions combine to form similar sub-structures. Pairs of NeH/N hydrogen bonds and p$$$dp stacking interactions produce dimers in all compound. The compounds with the best anti-mycobacterial activity were found to be 1c (aryl ¼ 2-O2NC6H4), 1d, (aryl ¼ 2-HOC6H4), 1e and 1h, all having superior activities to that of the standard drug, ethambutol. Moreover two of these compounds have the capacity to act as tridentate ligands, namely 1d [a potential ONN chelator] and 1h [a potential NNN chelator]. Compound 1d (HL) acts as a tridentate O,N,N-donor to Cu(II) in forming the dimeric octahedral complex{[(L) (H2O)Cu][ O3SCF3]}2, 3, from Cu(II) (O3SCF3)2 in moist MeOH. The monomeric square-pyramidal [(L) (H2O)Cu][ O3SCF3], with an axial OS(O2)CF3 ligand and equatorial H2O ligand, dimerizes through extensive p$$$p interactions involving two complete planar L-Cu fragments. The dimers are linked into a three dimensional array by OeH/O and NeH/O hydrogen bonds and by further p$$$p interactions. Complex 3, while still very active, has only about 40% of the activity of its ligand against M. tuberculosis ATTC 27294.
Keywords: 2-Arylidenehydrazinylbenzothiazole derivatives
Crystal structure
Anti-TB activity
Copper complex
Imino/amino tautomers
Issue Date: 2019
Publisher: Elsevier
Citation: PINHEIRO, Alessandra C. et al. Synthesis, potent anti-TB activity against M. tuberculosis ATTC 27294, crystal structures and complex formation of selected 2-arylidenehydrazinylbenzothiazole derivatives. Journal of Molecular Structure, 1178, p. 655-668, 2019.
DOI: 10.1016/j.molstruc.2018.10.030
ISSN: 0022-2860
Copyright: restricted access
Appears in Collections:Farmanguinhos - Artigos de Periódicos
INI - Artigos de Periódicos

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