Work

Synthesis of 4′/5′-Spirocyclopropanated Uridine and d -Xylouridine Derivatives and Their Activity against the Human Respiratory Syncytial Virus

Year: 2019

Type: article

Abstract: The Simmons-Smith-Furukawa reaction was used to generate 4'/5'-spirocyclopropanated uridine analogs from electron-rich exocyclic enol esters. During synthesis, the native hydroxylation pattern of the nucleoside is preserved and offers the possibility for a late stage 5'-phosphorylation at the spirocyclopropanol moiety. All synthesized spirocyclopropanated uridine derivatives, including the corresponding 5'-monophosphate (cpUMP), were evaluated with respect to their antiviral activity in an HRSV assay showing moderate, but promising activity.

Source: Organic Letters

DOI: 10.1021/acs.orglett.9b02555

Authors: Christoph Köllmann, Svenja M. Wiechert, Peter G. Jones, Thomas Pietschmann, Daniel B. Werz

Institutions: Technische Universität Braunschweig, Helmholtz Centre for Infection Research, Center for Experimental and Clinical Infection Research

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: green

Funders: Fonds der Chemischen Industrie, Studienstiftung des Deutschen Volkes, Helmholtz-Alberta Initiative