1206907-39-2Relevant articles and documents
Aminodi(hetero)arylamines in the thieno[3,2-b]pyridine series: Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using non-tumor cells
Calhelha, Ricardo C.,Ferreira, Isabel C. F. R.,Peixoto, Daniela,Abreu, Rui M. V.,Vale-Silva, Luis A.,Pinto, Eugenia,Lima, Raquel T.,Alvelos, M. Ines,Vasconcelos, M. Helena,Queiroz, Maria-Joao R. P.
, p. 3834 - 3843 (2012)
Three aminodi(hetero)arylamines were prepared via a palladium-catalyzed C-N Buchwald-Hartwig coupling of methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate with different bromonitrobenzenes, followed by reduction of the nitro groups of the coupling products to the corresponding amino compounds. The aminodi(hetero)arylamines thus obtained were evaluated for their growth inhibitory effect on four human tumor cell lines MCF-7 (breast adenocarcinoma), A375-C5 (melanoma), NCI-H460 (non-small cell lung cancer) and HepG2 (hepatocellular carcinoma). The toxicity to non-tumor cells was also evaluated using a porcine liver primary cell culture (PLP1), established by us. The aminodi(hetero)arylamine with the NH2 group in the ortho position and an OMe group in the para position to the NH of the di(hetero)arylamine, is the most promising compound giving the lowest GI50 values (1.30-1.63 μM) in all the tested human tumor cell lines, presenting no toxicity to PLP1 at those concentrations. The effect of this compound on the cell cycle and induction of apoptosis was analyzed in the NCI-H460 cell line. It was observed that it altered the cell cycle profile causing a decrease in the percentage of cells in the G0/G1 phase and an increase of the apoptosis levels.
Synthesis of new thieno[3,2-b]pyridine derivatives by palladium-catalyzed couplings and intramolecular cyclizations
Calhelha, Ricardo C.,Queiroz, Maria-Jo?o R.P.
scheme or table, p. 281 - 283 (2010/03/26)
Two methyl 3-aminothieno[3,2-b]pyridine-2-carboxylates were prepared from 3-fluoro or 3-nitropicolinonitriles and methyl thioglycolate in DMF/KOH(aq). From the unsubstituted precursor in the pyridine ring, di(hetero)arylamines were obtained by C-N Buchwald-Hartwig coupling with bromonitrobenzenes and with 2-bromopyridine. In the latter case a tetracyclic compound was formed by intramolecular cyclization. Using a brominated derivative in the pyridine ring as a coupling component, it was possible to synthesize C-C (Suzuki and Sonogashira) and C-N (Buchwald-Hartwig) coupling products and a tetracyclic compound obtained by bifunctionalization of the thienopyridine system.
