| Author | Pinheiro, Alessandra C. | |
| Author | Souza, Marcus V. N. de | |
| Author | Lourenço, Maria C. S. | |
| Author | Costa, Cristiane F. da | |
| Author | Baddeley, Thomas C. | |
| Author | Low, John N. | |
| Author | Wardell, Solange M. S. V. | |
| Author | Wardell, James L. | |
| Access date | 2019-03-29T13:05:20Z | |
| Available date | 2019-03-29T13:05:20Z | |
| Document date | 2019 | |
| 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. | pt_BR |
| ISSN | 0022-2860 | pt_BR |
| URI | https://www.arca.fiocruz.br/handle/icict/32290 | |
| Language | eng | pt_BR |
| Publisher | Elsevier | pt_BR |
| Rights | restricted access | pt_BR |
| Title | Synthesis, potent anti-TB activity against M. tuberculosis ATTC 27294, crystal structures and complex formation of selected 2-arylidenehydrazinylbenzothiazole derivatives | pt_BR |
| Type | Article | |
| DOI | 10.1016/j.molstruc.2018.10.030 | |
| 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. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Departamento de Bacteriologia. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK. | pt_BR |
| Affilliation | University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK. | pt_BR |
| Affilliation | CHEMSOL. Aberdeen, Scotland, UK. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil / University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK. | pt_BR |
| Subject | Crystal structure | pt_BR |
| Subject | Anti-TB activity | pt_BR |
| Subject | Copper complex | pt_BR |
| Subject | Imino/amino tautomers | pt_BR |
| Embargo date | 2023-03-01 | |
