16586-67-7Relevant articles and documents
Synthesis, potent anti-TB activity against M. tuberculosis ATTC 27294, crystal structures and complex formation of selected 2-arylidenehydrazinylbenzothiazole derivatives
Pinheiro, Alessandra.C.,de Souza, Marcus.V.N.,Louren?o, Maria.C.S.,da Costa, Cristiane F.,Baddeley, Thomas C.,Low, John N.,Wardell, Solange.M.S.V.,Wardell, James L.
, p. 655 - 668 (2019)
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 55–75%. The crystal structure determination of compounds, 1e (aryl = 4-MeOC6H4), 1h (aryl = pyridin-2-yl), 1f (aryl = 2-HO-5-MeC6H3) revealed amino forms, whereas an imino form was found for 1f (aryl = 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 N–H?N hydrogen bonds and π···dπ stacking interactions produce dimers in all compound. The compounds with the best anti-mycobacterial activity were found to be 1c (aryl = 2-O2NC6H4), 1d, (aryl = 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 π···π interactions involving two complete planar L-Cu fragments. The dimers are linked into a three dimensional array by O–H?O and N–H?O hydrogen bonds and by further π···π interactions. Complex 3, while still very active, has only about 40% of the activity of its ligand against M. tuberculosis ATTC 27294.
Arylhydrazones Derivatives Containing a Benzothiazole Moiety, Efficient Ligands in the Palladium-Catalyzed Mizoroki–Heck and Suzuki–Miyaura Cross-coupling Reactions under IR Irradiation
Ortega-Jiménez, Fernando,Penieres-Carrillo, José Guillermo,López-Cortés, José Guadalupe,Carmen Ortega-Alfaro,Lagunas-Rivera, Selene
, p. 1881 - 1888 (2017/09/12)
A simple arylhydrazone containing the benzothiazole moiety which may be used as an efficient ligand in the palladium-catalyzed Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions, under infrared irradiation as an alternative source of energy, is presented. The reactions proceeded with extremely high efficiency under mild conditions and produced very good yields.
Synthesis of new triazolo and pyrazolo benzothiazoles
Deshmukh,Patil,Jadhav,Shejwal
, p. 163 - 166 (2013/09/23)
Benzothiazole-2-thiol 1 on heating with excess of hydrazine hydrate yields 2-hydrazino-1,3-benzothiazole (2). Compound 2 on reaction with carbon disulfide in alkaline medium affords [1,2,4] triazolo [3,4-b] [1,3] benzothiazole-3-thiol (3). Condensation of 2 with various substituted aryl aldehydes yields corresponding hydrazine derivatives (4), which on cyclisation with acetic anhydride gave corresponding [1,2,4] triazolo [3,4-6] [1,3] benzothiazoles (5). Some other triazolo derivatives (6,7,8) of benzothiazole were obtained by the cyclization of 2 with benzoyl chloride, acetyl chloride and formic acid respectively. Again compound 2 on condensation with acetyl acetone and ethylacetoacetate gives pyrazolo derivatives (9,10) respectively. The synthesized compounds were characterized by elemental and spectral analysis.
