Molecular orbital studies on nucleoside antibiotics: Part IX. Conformation of 5-ethynyl- and 5-vinyl-2′-deoxycytidines

Abstract

5-Substituted deoxycytidines exhibit antiviral and antimetabolic properties and they are selective inhibitors of herpes simplex virus (HSV). Conformational properties of two of the 5-substituted deoxycytidines, namely: 5-ethynyl- and 5-vinyl-2′-deoxycytidines, have been investigated by the PCILO method and compared with those of their parent nucleoside (2′-deoxycytidine). The results indicate striking similarity in their conformational behaviour. This result has important biological significance in terms of their biological activity. The mechanism of their action is discussed.