Document Detail


Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.
MedLine Citation:
PMID:  17485204     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
We report the synthesis of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) and 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives and their evaluation against HIV-1 and HIV-2. In addition, we conducted molecular modeling studies on both d4U and ddU monophosphates to investigate their second phosphorylation process. The findings from the modeling studies provide compelling evidence for the lack of anti-HIV activity of d4U phosphoramidates, in contrast with the corresponding ddU phosphoramidates.
Authors:
Youcef Mehellou; Christopher McGuigan; Andrea Brancale; Jan Balzarini
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Publication Detail:
Type:  Journal Article     Date:  2007-04-22
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  17     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2007 Jul 
Date Detail:
Created Date:  2007-06-18     Completed Date:  2007-09-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  3666-9     Citation Subset:  IM    
Affiliation:
Welsh School of Pharmacy, Cardiff University, King Edward VII Avenue, Cardiff, UK.
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MeSH Terms
Descriptor/Qualifier:
Amides / chemistry*
Anti-HIV Agents / chemical synthesis*,  chemistry
Chemistry, Pharmaceutical / methods*
Dideoxynucleosides / chemical synthesis*,  chemistry*
Drug Design
HIV-1 / metabolism
HIV-2 / metabolism
Models, Chemical
Models, Molecular
Nucleoside-Phosphate Kinase / chemistry
Nucleosides / chemistry
Phosphates / chemistry
Phosphoric Acids / chemistry*
Phosphorylation
Thymidine Monophosphate / chemistry
Chemical
Reg. No./Substance:
0/Amides; 0/Anti-HIV Agents; 0/Dideoxynucleosides; 0/Nucleosides; 0/Phosphates; 0/Phosphoric Acids; 2817-45-0/phosphoramidic acid; 365-07-1/Thymidine Monophosphate; 5974-93-6/2',3'-didehydro-2',3'-dideoxyuridine; 5983-09-5/2',3'-dideoxyuridine; EC 2.7.4.4/Nucleoside-Phosphate Kinase; EC 2.7.4.9/dTMP kinase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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