Abstract
Carbocyclic analogues of 2'-azido- and 2'-amino-2'-deoxycytidine, compounds 8 and 9, were synthesized by an eight-step synthesis from (+/-)-(1 alpha,2 alpha,3 beta,5 beta)-3-amino-5-(hydroxymethyl)-1,2- cyclopentanediol (1), which was prepared from cyclopentadiene via an eight-step route. These compounds were tested in vitro against herpes simplex virus type 1 (HSV-1). The 2'-amino analogue was found to show moderate antiviral activity, with an ED50 of 50 microM. However, the 2'-azido analogue was not active at a concentration up to 400 microM.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / pharmacology
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Cytidine / analogs & derivatives*
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Cytidine / chemical synthesis
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Cytidine / pharmacology
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Deoxycytidine / analogs & derivatives*
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Deoxycytidine / chemical synthesis
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Deoxycytidine / pharmacology
Substances
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Antiviral Agents
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Deoxycytidine
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4-amino-1-(2-azido-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-2(1H)-pyrimidinone
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1-(2-amino-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-2(1H)-pyrimidinone
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2'-azidocytidine
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Cytidine