Synthesis and antiviral evaluation of carbocyclic analogues of 2'-azido- and 2'-amino-2'-deoxycytidine.
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.
Lin
T S
TS
Department of Pharmacology, Yale University School of Medicine, New Haven, Connecticut 06510.
Zhang
X H
XH
Wang
Z H
ZH
Prusoff
W H
WH
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000998:Antiviral Agents; D003841:Deoxycytidine; C054824:4-amino-1-(2-azido-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-2(1H)-pyrimidinone; C054826:1-(2-amino-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-2(1H)-pyrimidinone; C015010:2'-azidocytidine; D003562:Cytidine