182691-76-5Relevant academic research and scientific papers
Furo[3,2-b]pyridine: A Privileged Scaffold for Highly Selective Kinase Inhibitors and Effective Modulators of the Hedgehog Pathway
Němec, Václav,Hylsová, Michaela,Maier, Luká?,Flegel, Jana,Sievers, Sonja,Ziegler, Slava,Schr?der, Martin,Berger, Benedict-Tilman,Chaikuad, Apirat,Val?íková, Barbora,Uldrijan, Stjepan,Drápela, Stanislav,Sou?ek, Karel,Waldmann, Herbert,Knapp, Stefan,Paruch, Kamil
supporting information, p. 1062 - 1066 (2019/01/04)
Reported is the identification of the furo[3,2-b]pyridine core as a novel scaffold for potent and highly selective inhibitors of cdc-like kinases (CLKs) and efficient modulators of the Hedgehog signaling pathway. Initially, a diverse target compound set was prepared by synthetic sequences based on chemoselective metal-mediated couplings, including assembly of the furo[3,2-b]pyridine scaffold by copper-mediated oxidative cyclization. Optimization of the subseries containing 3,5-disubstituted furo[3,2-b]pyridines afforded potent, cell-active, and highly selective inhibitors of CLKs. Profiling of the kinase-inactive subset of 3,5,7-trisubstituted furo[3,2-b]pyridines revealed sub-micromolar modulators of the Hedgehog pathway.
FUROPYRIDINES AS INHIBITORS OF PROTEIN KINASES
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Page/Page column 38, (2015/11/23)
The invention relates to furo[3,2-b]pyridines substituted at least in position 5 as inhibitors of protein kinases, regulators or modulators, methods of preparation thereof, pharmaceutical compositions containing the compounds, and pharmaceutical use of the compounds and compositions in the treatment of the diseases such as, for example, cancer or neurodegenerative diseases. (Formula (I))
Furopyridines. XVII [1]. Cyanation, chlorination and nitration of furo[3,2-b]pyridine N-oxide
Shiotani, Shunsaku,Taniguchi, Katsunori
, p. 1051 - 1056 (2007/10/03)
The N-oxide 2 of furo[3,2-b]pyridine (1) was cyanated by the Reissert-Henze reaction with potassium cyanide and benzoyl chloride to give 5-cyano derivative 3, which was converted to the carboxamide 4, carboxylic acid 5, ethyl ester 6 and ethyl imidate 8. Chlorination of 2 with phosphorus oxychloride yielded 2-9a, 3- 9b, 5- 9c and 7-chloro derivative 9d. Reaction of 9d with sodium methoxide, pyrrolidine, N,N-dimethylformamide and ethyl cyanoacetate afforded 7-methoxy- 10, 7-(1-pyrrolidyl)- 11 and 7-dimethylaminofuro[3,2-b]pyridine (14) and 7-(1-cyano-1-ethoxy-carbonyl)methylene-4,7-dihydro-furo[3,2-b]pyridine (12). Nitration of 2 with a mixture of fuming nitric acid and sulfuric acid gave 2-nitrofuro[3,2-b]pyridine N-oxide (15).
