Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases

0436360 - ÚEB 2015 RIV US eng J - Journal Article
Vilkauskaite, G. - Schaaf, P. - Sackus, A. - Kryštof, Vladimír - Holzer, W.
Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases.
Arkivoc. -, č. 2 (2014), s. 135-149. ISSN 1551-7004. E-ISSN 1551-7012
Institutional support: RVO:61389030
Keywords : Pyrazolones * Sonogashira reaction * multi-component reactions
Subject RIV: CC - Organic Chemistry
Impact factor: 1.165, year: 2014
http://www.arkat-usa.org/get-file/48428/

A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c]pyridines is described. The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl(hetero) arenes followed by pyridine ring formation of the coupling products in the presence of tert-butylamine, directly affording the title compounds. A congener without substituent at N-1 was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (H-1, C-13 and N-15) were undertaken with the obtained compounds. Selected representatives were evaluated for their potential as inhibitors of protein kinases.
Permanent Link: http://hdl.handle.net/11104/0240122