A novel class of trans-configurated difluorinated cyclopropanoic nucleoside analogues containing a methylene spacer between the cyclopropane ring and the heterocycle has been prepared. Some of these compounds showed weak anti-HIV activity in preliminary screenings.
Synthesis of Highly Flexible Difluorinated Cyclopropanoid Nucleoside Analogues. -The incorporation of fluorine substituents, cf. title compounds of type (I), may be of advantage for an improved biological activity, for higher bioavailability as well as for causing a retarded metabolism. -(CSUK, R.; EVERSMANN, L.; Z. Naturforsch., B: Chem. Sci. 59 (2004) 1, 77-94; Inst. Org. Chem., Martin-Luther-Univ. Halle-Wittenberg, D-06120 Halle/S., Germany; Eng.) -C. Oppel 22-215
A novel class of difluorinated cyclopropanoic nucleoside analogues containing a hydroxypropyl group and a methylene spacer between the difluorocyclopropane ring and the heterocycle has been prepared.
Synthesis of Flexible Difluorinated Cyclopropanoid Nucleoside Analogues. -A novel class of difluorinated cyclopropanoid nucleoside analogues is synthesized. Coupling of a cyclopropane derivative with adenine or the appropriate pyrimidine base proceeds under Mitsunobu conditions to afford the protected adenine analogue. The latter is subsequently deacetylated using a catalytic amount of sodium methylate in methanol. Cis-and trans-substituted cyclopropane derivatives are treated in the same manner. Deacetylation and debenzoylation of (XIV) is performed in 2 steps to avoid decomposition under treatment with sodium hydroxide. -(CSUK, R.; EVERS-MANN, L.
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