Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus.

Autor:	Köllmann C; Technische Universität Braunschweig, Institute for Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany., Sake SM; Institute for Experimental Virology, TWINCORE, Centre for Experimental and Clinical Infection Research, A Joint Venture Between the Medical School Hannover (MHH) and the Helmholtz Centre for Infection Research (HZI), Hannover, Feodor-Lynen-Str. 7, 30625 Hannover, Germany., Jones PG; Technische Universität Braunschweig, Institute for Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany., Pietschmann T; Institute for Experimental Virology, TWINCORE, Centre for Experimental and Clinical Infection Research, A Joint Venture Between the Medical School Hannover (MHH) and the Helmholtz Centre for Infection Research (HZI), Hannover, Feodor-Lynen-Str. 7, 30625 Hannover, Germany., Werz DB; Technische Universität Braunschweig, Institute for Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2020 Mar 20; Vol. 85 (6), pp. 4267-4278. Date of Electronic Publication: 2020 Feb 26.
DOI:	10.1021/acs.joc.9b03425
Abstrakt:	Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as key intermediates, we synthesized a variety of C4'-methylated d-ribose and l-lyxose-configured uridine derivatives by a base-mediated ring-opening of the spirocyclopropanol moiety. Investigations of antiviral activity against the human respiratory syncytial virus were carried out for selected derivatives, showing moderate activity.
Databáze:	MEDLINE
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