77355-98-7Relevant articles and documents
Synthesis and Antiviral Activity of 5--2'-deoxyuridine
Huang, Guang-Fu,Okada, Masashi,Clercq, Erik De,Torrence, Paul F.
, p. 390 - 393 (1981)
To study the influence of substitution of CN for CCH in the anti-herpes virus nucleoside 5-(propynyloxy)-2'-deoxyuridine (1), 5--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--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 3H>dThd or 3H>dUrd into DNA of PRK cells; however, its anti-herpes virus activity was completely prevented upon the addition of either dThd or dUrd.