Design and racemic synthesis of conformationally restricted carbocyclic pyrimidine nucleoside analogs based on the structure of the L-nucleoside residue in heterochiral DNA

H Urata; H Miyagoshi; H Kakuya; H Tokumoto; T Kawahata; T Otake; M Akagi

doi:10.1248/cpb.46.458

Design and racemic synthesis of conformationally restricted carbocyclic pyrimidine nucleoside analogs based on the structure of the L-nucleoside residue in heterochiral DNA

Chem Pharm Bull (Tokyo). 1998 Mar;46(3):458-61. doi: 10.1248/cpb.46.458.

Authors

H Urata¹, H Miyagoshi, H Kakuya, H Tokumoto, T Kawahata, T Otake, M Akagi

Affiliation

¹ Osaka University of Pharmaceutical Sciences, Takatsuki, Japan.

PMID: 9549888
DOI: 10.1248/cpb.46.458

Abstract

Carbocyclic pyrimidine nucleoside analogs which have restricted glycosidic conformation at chi approximately 180 degrees were designed, based on the conformational features of the L-nucleotide residue in heterochiral DNA, and synthesized. The synthesis of (+/-)-carbocyclic 6,6'-O-cyclo-2'-deoxyuridine was achieved via bromination and subsequent intramolecular cyclization of carbocyclic 6'beta-hydroxy-2'-deoxyuridine. (+/-)-Carbocyclic 6,6'-O-cyclo-2'-deoxycytidine was synthesized from protected carbocyclic 6,6'-O-cyclo-2'-deoxyuridine via the 4-triazole intermediate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / pharmacology
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / pharmacology
Cells, Cultured / drug effects
Cytidine / analogs & derivatives*
Cytidine / chemical synthesis
Cytidine / pharmacology
Drug Design
HIV-1 / drug effects
Pyrimidine Nucleosides / chemical synthesis*
Pyrimidine Nucleosides / pharmacology

Substances

Anti-HIV Agents
Bridged Bicyclo Compounds, Heterocyclic
Pyrimidine Nucleosides
carbocyclic 6,6'-O-cyclo-2'-deoxycytidine
Cytidine