68775-20-2Relevant academic research and scientific papers
Multicomponent synthesis, in?vitro cytotoxic evaluation and molecular modelling studies of polyfunctionalized pyrazolo[3,4-b]pyridine derivatives against three human cancer cell lines
Aggarwal, Ranjana,Kumar, Suresh,Sadana, Rachna,Guzman, Andrea,Kumar, Virender
supporting information, p. 3308 - 3324 (2021/09/16)
A series of diversely polyfunctionalized pyrazolo[3,4-b]pyridines were synthesized by the multicomponent reaction of phenyl/benzothiazolylhydrazine and 3-oxo-3-arylpropanenitrile with 1,3-diketones under solvent-free and solvent-mediated conditions. Nineteen pyrazolo[3,4-b]pyridine derivatives were screened for their anti-cancer activity against three human cancer cell lines namely NALM-6, SB-ALL and MCF-7. Non-fluorinated 1-(benzothiazolyl)pyrazolo[3,4-b]pyridines (6a–d) displayed better cytotoxicity results as compared to other tested derivatives. The compound 1-(benzothiazolyl)-4,6-dimethyl-3-(4-chlorophenyl)pyrazolo[3,4-b]pyridine, 6b, was identified as the most active derivative with 53% cell growth inhibition nearly equal to the standard drug doxorubicin (58%), in close agreement to drug-likeness and drug score predictions. Among the fluorinated derivatives, compound 2-(3-(4-chlorophenyl)-4-methyl-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzo[d]thiazole, 12c, was identified as hit compound with 46-39% cell growth inhibition against all the tested cell lines. Compound 6b was found to display suitable binding when docked inside the active site of Aurora-A kinase enzyme.
Multi-component solvent-free versus stepwise solvent mediated reactions: Regiospecific formation of 6-trifluoromethyl and 4-trifluoromethyl-1H- pyrazolo[3,4-b]pyridines
Aggarwal, Ranjana,Kumar, Virender,Bansal, Anshul,Sanz, Dionisia,Claramunt, Rosa M.
experimental part, p. 31 - 37 (2012/08/08)
A simple and efficient regiospecific synthesis of 6-trifluoromethyl-1H- pyrazolo[3,4-b]pyridines has been achieved in excellent yields via a three-component reaction between 2-hydrazinobenzothiazoles, α- cyanoacetophenones and trifluoromethyl-β-diketones under solvent-free conditions. This method was found to be more convenient than the classical stepwise solvent mediated process, which furnished not only the opposite regioisomer i.e. 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines (50-60%) but also an undesired amide, 5-acetylamino-1-(benzothiazol-2′-yl)-3-phenyl-1H- pyrazole as a side product. The structure of the two regioisomers was established with certainty on the basis of rigorous analysis of 1H, 13C, 19F-NMR spectral data and (1H 13C) gs-HMQC, (1H13C) gs-HMBC experiments.
