Nucleosides having acyclic 2-deoxy-1-thio-d-arabino-hexitol and 2-deoxy-1-thio-d-erythro-pentitol chains

Horton, Derek; Markovs, Robert A.

doi:10.1016/s0008-6215(00)84879-x

Cited by 7 publications

(1 citation statement)

References 12 publications

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“…In our recent reports 11,12 we described the synthesis of 4′-S-Thd by a coupling reaction of benzyl 3,5-di-Obenzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (1a) 16 with 2,4-bis-O-(trimethylsilyl)-5-methyluracil in the presence of mercuric bromide and cadmium carbonate according to the method of Horton and Markovs 17 (Scheme 1, R ) CHdCHBr). For the synthesis of additional analogues, we have modified this methodology and replaced the mercury and cadmium reagents with alternative thiophilic promoters such as N-bromoor N-iodosuccinimide in the presence of molecular sieves, as exemplified by Sugimura and co-workers, 18,19 but using acetonitrile as solvent instead of dichloromethane.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

Trivedi

et al. 1996

J. Med. Chem.

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A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridine (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella zoster virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

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