Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine
- 31 March 1981
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 24 (4), 390-393
- https://doi.org/10.1021/jm00136a007
Abstract
To study the influence of substitution of CN for C.tbd.CH in the anti-herpes virus nucleoside 5-(propynyloxy)-2''-deoxyuridine (1), 5-[(cyanomethylene)oxy]-2''-deoxyuridine (2) was prepared. When the potassium salt of 5-hydroxy-2''-deoxyuridine was reacted with iodoacetonitrile, the bisalkylated product 3-(cyanomethyl)-5-[(cyanomethylene)oxy]-2''-deoxyuridine (3) was the major product with a lesser amount of 3-(cyanomethyl)-5-hydroxy-2''-deoxyuridine (5) and only a trace amount of the desired product (2). When 5-hydroxy-2''-deoxyuridine was alkylated in water in the presence of 1 equivalent of KOH, compound 2 was the major product. In cultures of primary rabbit kidney (PRK) cells, compound 2 showed an anti-herpes virus activity that was comparable to that of 1 and ara-A. Compound 2 did not inhibit incorporation of [Me-3H]dThd or [1'',2''-3H]dUrd into DNA of PRK cells, its anti-herpes virus activity was completely prevented upon the addition of dThd or dUrd.This publication has 7 references indexed in Scilit:
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