The Identification of a Novel Highly Condensed Pentacyclic Heteroaromatic Ring System 1,3,5,5b,6,8,10,10b-Octaazacyclopenta[h,i]Aceanthrylene and its Application in the Synthesis of 5,7-Substituted Pyrazolo[4,3-d]Pyrimidines

0446805 - ÚEB 2016 RIV US eng J - Journal Article
Havlíček, Libor - Moravcová, Daniela - Kryštof, Vladimír - Strnad, Miroslav
The Identification of a Novel Highly Condensed Pentacyclic Heteroaromatic Ring System 1,3,5,5b,6,8,10,10b-Octaazacyclopenta[h,i]Aceanthrylene and its Application in the Synthesis of 5,7-Substituted Pyrazolo[4,3-d]Pyrimidines.
Journal of Heterocyclic Chemistry. Roč. 52, č. 3 (2015), s. 669-673. ISSN 0022-152X. E-ISSN 1943-5193
R&D Projects: GA ČR GAP305/12/0783
Institutional support: RVO:61389030
Keywords : roscovitine * pyrazolo[4,3-d]pyrimidine * kinase inhibitor
Subject RIV: CE - Biochemistry
Impact factor: 0.685, year: 2015

Pyrazolo[4,3-d]pyrimidines are of interest as potential kinase inhibitors. This article describes the formation of a novel highly conjugated, condensed, centrosymmetric heteroaromatic compound, 4,9-dichloro-2,7-diisopropyl-1,3,5,5b,6,8,10,10b-octaazacyclopenta[h,i]aceanthrylene (3), during the chlorination of 5,7-dihydroxypyrazolo[4,3-d]pyrimidine (1) with phenylphosphonic dichloride. The nucleophilic attack of benzylamine on 3 afforded N-benzyl-5-chloro-3-isopropyl-1H-pyrazolo[4,3-d]pyrimidin-7-amine (6), which was further substituted to yield a pyrazolo[4,3-d]pyrimidine analogue of roscovitine, a well-known cyclin-dependent kinase inhibitor.
Permanent Link: http://hdl.handle.net/11104/0248761