Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis and Biological Evaluation of Phosphonopyrimidine and Phosphonopurine Ribonucleosides
MIKIO HONJOTOKUMI MARUYAMAMITZUYO HORIKAWAJAN BALZARINIERIK De CLERCQ
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JOURNAL FREE ACCESS

1987 Volume 35 Issue 8 Pages 3227-3234

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Abstract
Treatment of lithiated 2', 3', 5'-tri-Ο-protected uridine and 6-chloropurine ribonucleoside with diethyl chlorophosphate, followed by deblocking (and amination) and hydrolysis, provided 5-and 6-phosphonouridine (IV and VII), and 8-phosphonoadenosine (Xb), respectively. The Arbuzov reaction of 2', 3', 5'-tri-Ο-protected 4-chloro-2 (1H) -pyrimidinone ribonucleoside and triethyl phosphite afforded the diethyl 4-phosphonate derivative (XII). Compounds IV, VII and Xb, and their respective diethyl esters (IIb and VIb) and monoethyl ester (Xa) were inactive in vitro as antiviral and cytostatic agents, but the diethyl 8-phosphonate derivative (IXb) of 6-chloro-9- (β-D-ribofuranosyl) purine (VIIIa) showed some antiviral and cytostatic activities, which were comparable in all respects to those of VIIIa.
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© The Pharmaceutical Society of Japan
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