Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus.
Cast your vote
You can rate an item by clicking the amount of stars they wish to award to this item.
When enough users have cast their vote on this item, the average rating will also be shown.
Your vote was cast
Thank you for your feedback
Thank you for your feedback
MetadataShow full item record
AbstractAdjusting 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.
CitationJ Org Chem. 2020 Mar 20;85(6):4267-4278. doi: 10.1021/acs.joc.9b03425. Epub 2020 Feb 26.
AffiliationTWINCORE, Zentrum für experimentelle und klinische Infektionsforschung GmbH,Feodor-Lynen Str. 7, 30625 Hannover, Germany.
PublisherAmerican Chemical Society
JournalThe Journal of organic chemistry
The following license files are associated with this item:
- Creative Commons
- Synthesis of 4'/5'-Spirocyclopropanated Uridine and d-Xylouridine Derivatives and Their Activity against the Human Respiratory Syncytial Virus.
- Authors: Köllmann C, Wiechert SM, Jones PG, Pietschmann T, Werz DB
- Issue date: 2019 Sep 6
- 3'-C-branched 2'-deoxy-5-methyluridines: synthesis, enzyme inhibition, and antiviral properties.
- Authors: Fedorov II, Kazmina EM, Novicov NA, Gurskaya GV, Bochkarev AV, Jasko MV, Victorova LS, Kukhanova MK, Balzarini J, De Clercq E
- Issue date: 1992 Nov 27
- Stereoselective synthesis of sugar-modified enyne analogues of adenosine and uridine. Interaction with S-adenosyl-L-homocysteine hydrolase and antiviral and cytotoxic effects.
- Authors: Wnuk SF, Lewandowska E, Sacasa PR, Crain LN, Zhang J, Borchardt RT, De Clercq E
- Issue date: 2004 Oct 7
- Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV).
- Authors: Lin TS, Luo MZ, Liu MC, Pai SB, Dutschman GE, Cheng YC
- Issue date: 1994 Mar 18
- Synthesis of 3'-deoxynucleosides with 2-oxabicyclo[3.1.0]hexane sugar moieties: addition of difluorocarbene to a 3',4'-unsaturated uridine derivative and 1,2-dihydrofurans derived from D- and L-xylose1.
- Authors: Nowak I, Robins MJ
- Issue date: 2007 Apr 27