93752-20-6Relevant academic research and scientific papers
Synthesis and antiproliferative activity in vitro of new 2-thioxoimidazo[4,5-b]pyridine derivatives
Nowicka, Anna,Liszkiewicz, Hanna,Nawrocka, Wanda P.,Wietrzyk, Joanna,Zubiak, Agnieszka,Ko?odziejczyk, Wojciech
, p. 101 - 111 (2015/02/05)
Two series of 2-thioxoimidazo[4,5-b]pyridine derivatives have been synthesized from 2,3-diaminopyridine (1) and 5-halogenosubstituted-2,3-diaminopyridines 2, 3. Mannich bases 7 - 12 and 24 - 29, derivatives of 1-arylamino-6-halogeno-2-thioxoimidazo[4,5-b]pyridine were obtained with selected secondary amines: morpholine, piperidine, 2-methoxyphenylpiperazine, pyrimidyn-2-yl-piperazine and formaldehyde in ethanol. The structures 7 - 12 and 24 - 29 were confirmed by the results of elementary analysis and their IR,1H-NMR and MS spectra. All given structures 7 - 12 have been optimized to get the most stable low energy conformers. Synthesized compounds were of interest for biological studies or can be substrates for further synthesis. The selected compounds 7 - 10, 12 - 17, 22, 25, 27 - 29 were screened for their antiproliferative activity in vitro against human cancer and normal mouse fibroblast cell lines.
Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)
Chang, Lei,Lee, Sang-Yong,Leonczak, Piotr,Rozenski, Jef,De Jonghe, Steven,Hanck, Theodor,Müller, Christa E.,Herdewijn, Piet
, p. 10080 - 10100 (2015/02/05)
Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.
THIONATION OF IMIDAZOPYRIDINES
Yutilov, Yu.M.,Svertilova, I.A.
, p. 653 - 658 (2007/10/02)
Direct thionation of imidazopyridines and imidazopyridines results in the formation of their 2-thioxo derivatives, usually in high yield.The thione structure of the imidazopyridines obtained has been confirmed from their IR spectra in the solid state and in solution.The general nature of the thionation of imidazole, benzimidazole, imidazopyridine, imidazopyridine, and purine has been noted as one of the distinctive chemical properties of compounds in this series of nitrogen heterocycles.
