Synthesis and antiviral and cytotoxic activity of iodohydrin and iodomethoxy derivatives of 5-vinyl-2'-deoxyuridines, 2'-fluoro-2'-deoxyuridine, and uridine

R Kumar, L Xu, EE Knaus, LI Wiebe…

Index: Kumar, Rakesh; Xu, Lihua; Knaus, Edward E.; Wiebe, Leonard I.; Tovell, Dorothy R.; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 717 - 723

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Citation Number: 30

Abstract

'Reagents:(i) CH2= CHC02Et,(Ph3P) 2PdC12, EgN (7b, c);(ii) 0.5 N KOH (8b, c);(iii) DMF, EgN, 100" C (9b, c). thought to undergo inactivation by hydroxylation of the C-5 substituent, in a manner analogous to that reported for 5-ethyl-2'-deoxyuridine (EDU, 6).* Although the structural requirements at C-5 are reasonably well-defined for antiherpetic activity, in vivo catabolism necessitates further structural manipulation to obtain agents which are more ...