Nucleosides. 1. 9-(3'-Alkyl-3'-deoxy-.beta.-D-ribofuranosyl)adenines as lipophilic analogs of cordycepin. Synthesis and preliminary biological studies
- 1 November 1976
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 19 (11) , 1265-1270
- https://doi.org/10.1021/jm00233a001
Abstract
A series of lipophilic 9-(3''-alkyl-3''-deoxy-.beta.-D-ribofuranosyl)adenines of increasing chain length was synthesized from the corresponding branched sugars via titanium chloride catalyzed ribosylation of chloromercuri-6-benzamidopurine. Enhanced growth inhibitory activity was observed against CCRF-CEM human lymphoblastic leukemia cells in culture as the length of the alkyl side chain in the sugar and the resultant lipophilic character of the nucleoside were increased. Experiments involving incorporation of radiolabeled uridine, thymidine and leucine revealed that in contrast to cordycepin (1) the 3''-n-butyl and 3''-n-hexyl analogs 5 and 6 inhibit not only RNA synthesis but DNA and protein synthesis as well.This publication has 4 references indexed in Scilit:
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