Prodrugs of 9-.beta.-D-arabinofuranosyladenine. 1. Synthesis and evaluation of some 5'-(O-acyl) derivatives
- 1 December 1978
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 21 (12), 1218-1221
- https://doi.org/10.1021/jm00210a009
Abstract
A number of 5''-(O-acyl) derivatives of 9-.beta.-D-arabinofuranosyladenine (ara-A, VIRA-A) were prepared by direct acylation of the parent nucleoside 1 in pyridine-N,N-dimethylformamide. These compounds, designed as prodrugs for 1, offer a range of solubilities and lipophilicities indicating for several examples improved solubility and the potential for improved membrane transport over 1. All are resistant to deactivation by adenosine deaminase. Of special interest is the 5''-(O-valeryl) derivative that shows a marked increase in antiviral activity over 1.This publication has 8 references indexed in Scilit:
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