High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

S A Poulsen; David James Young; R J Quinn

doi:10.1016/S0960-894X(00)00620-X

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High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

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High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

S A Poulsen, David James Young and R J Quinn

Bioorganic & Medicinal Chemistry Letters, Vol.11(2), pp.191-193

2001

DOI: https://doi.org/10.1016/S0960-894X(00)00620-X

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Abstract

Medicinal and Biomolecular Chemistry

Pharmacology and Pharmaceutical Sciences

Organic Chemistry

2 [4 (2 carboxyethyl)phenethylamino]adenosine 5' (n ethylcarboxamide)

4 amino 6 chloro 1 phenylpyrazolo[3,4 d]pyrimidine

adenosine A1 receptor

pyrazolo[3,4 d]pyrimidine derivative

unclassified drug

The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12. © 2001 Elsevier Science Ltd.

Details

Title: High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines
Authors: S A Poulsen (Author) - Griffith University
David James Young (Author) - Griffith University
R J Quinn (Author) - Griffith University
Publication details: Bioorganic & Medicinal Chemistry Letters, Vol.11(2), pp.191-193
Publisher: Pergamon
Date published: 2001
DOI: 10.1016/S0960-894X(00)00620-X
ISSN: 0960-894X
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449144802621
Output Type: Journal article

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