Journal of Medicinal Chemistry p. 390 - 393 (1981)
Update date:2022-08-04
Topics: Synthesis Antiviral Activity Experimental 5-<(Cyanomethylene)oxy>-2'-deoxyuridine Cyanomethylene Deoxyuridine
Huang, Guang-Fu
Okada, Masashi
Clercq, Erik De
Torrence, Paul F.
To study the influence of substitution of CN for C<*>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 in dry DMF, 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).In contrast, when 5-hydroxy-2'-deoxyuridine was alkylated in water in the presence of 1 equiv of KOH, compound 2 was the major product.In cultures of primary rabbit kindey (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
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Doi:10.1016/S0022-328X(00)82443-2
(1981)Doi:10.1248/cpb.13.22
(1965)Doi:10.1021/ic0000810
(2000)Doi:10.1023/A:1020809814260
(2002)Doi:10.1016/j.jorganchem.2004.06.035
(2004)Doi:10.1039/b505010c
(2005)