Čeština
EnglishThe 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
Havlíček L., Moravcová D., Kryštof V., Strnad M.
JOURNAL OF HETEROCYCLIC CHEMISTRY 52: 669-673, 2015
Keywords: roscovitine, pyrazolo[43-d]pyrimidine, kinase inhibitor, fluorescence
Abstract: 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.
DOI: 10.1002/jhet.2147
IEB authors: Libor Havlíček
JOURNAL OF HETEROCYCLIC CHEMISTRY 52: 669-673, 2015
Keywords: roscovitine, pyrazolo[43-d]pyrimidine, kinase inhibitor, fluorescence
Abstract: 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.
DOI: 10.1002/jhet.2147
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