2-(Benzylsulfanyl)-6-chloro-9-isopropylpurine, a Valuable Intermediate in the Synthesis of Diaminopurine Cyclin Dependent Kinase Inhibitors

Autor:	David Michel Adrien Taddei, Alexandra M. Z. Slawin, J. Derek Woollins
Rok vydání:	2005
Předmět:	biology Stereochemistry Organic Chemistry Leaving group Regioselectivity Alkylation chemistry.chemical_compound chemistry Cyclin-dependent kinase biology.protein Physical and Theoretical Chemistry Purine metabolism Derivative (chemistry) CDK inhibitor Hypoxanthine
Zdroj:	European Journal of Organic Chemistry. 2005:939-947
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200400748
Popis:	The synthetic potential of a novel precursor of 2,6-diaminopurine CDK inhibitors, 2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, is described. The Traube purine synthesis was chosen to prepare the required 2-(benzylsulfanyl)hypoxanthine intermediate. Attempts to prepare its purin-6-yl methanesulfonic ester analogue failed. Conversion to the 6-chloropurine derivative enabled the introduction of arylamines in the presence of catalytic amounts of acid. Further chemical variety was introduced on the purine through a regioselective Mitsunobu N-9 alkylation. Oxidative cleavage of the 2-(benzylsulfanyl) leaving group with an aliphatic amine was implemented as previously reported. Purvalanol A, a potent CDK inhibitor, was synthesised using this methodology. The template and intermediates were fully characterised by modern spectroscopic techniques and single-crystal X-ray diffraction. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
Databáze:	OpenAIRE
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