The Cyclohexene Ring as Bioisostere of a Furanose Ring: Synthesis and Antiviral Activity of Cyclohexenyl Nucleosides

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 12; pp. 1591 - 1597
• Main Authors: Herdewijn, Piet, De Clercq, Erik
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 18.06.2001; Elsevier
• Subjects: Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiviral agents; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; Biological and medical sciences; Cyclohexanes - chemistry; Cyclohexenes; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Guanosine - analogs & derivatives; Guanosine - chemistry; Guanosine - pharmacology; Hepatitis B virus - drug effects; Hepatitis B virus - enzymology; Herpesviridae - drug effects; Herpesviridae - enzymology; Inhibitory Concentration 50; Medical sciences; Models, Molecular; Molecular Conformation; Molecular Mimicry; Nucleosides - chemistry; Nucleosides - pharmacology; Pentoses - chemistry; Pharmacology. Drug treatments; Stereoisomerism; Thymidine Kinase - antagonists & inhibitors; Varicella zoster virus; Stereoisomer; Purine nucleoside; Herpesviridae; Alphaherpesvirinae; Conformational analysis; Orthohepadnavirus; Betaherpesvirinae; In vitro; Biological activity; Human cytomegalovirus; Virus; Racemic; Hepadnaviridae; Analog; Antiviral; Herpesvirus hominis; Hepatitis B virus; Chemical synthesis; Monocyclic compound; Ethylenic compound
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)00270-0

The application of the bioisosteric concept between a furanose ring and a cyclohexene ring in the nucleoside field has led to the discovery of new potent antiviral agents. Graphic