Literature DB >> 17485204

Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.

Youcef Mehellou1, Christopher McGuigan, Andrea Brancale, Jan Balzarini.   

Abstract

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.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17485204     DOI： 10.1016/j.bmcl.2007.04.043

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  7 in total

Review 1.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

2.  [d4U]-spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase.

Authors:  Yassir Younis; Roger Hunter; Clare I Muhanji; Ian Hale; Rajinder Singh; Christopher M Bailey; Todd J Sullivan; Karen S Anderson
Journal:  Bioorg Med Chem       Date:  2010-05-11       Impact factor: 3.641

3.  A mild and concise synthesis of aryloxy phosphoramidate prodrug of alcohols via transesterification reaction.

Authors:  Hanglu Ying; Jie Yao; Fan Wu; Yufen Zhao; Feng Ni
Journal:  RSC Adv       Date:  2022-04-29       Impact factor: 4.036

Review 4.  Prodrug approaches to improving the oral absorption of antiviral nucleotide analogues.

Authors:  Larryn W Peterson; Charles E McKenna
Journal:  Expert Opin Drug Deliv       Date:  2009-04       Impact factor: 6.648

Review 5.  Phosphoramidates and phosphonamidates (ProTides) with antiviral activity.

Authors:  Magdalena Slusarczyk; Michaela Serpi; Fabrizio Pertusati
Journal:  Antivir Chem Chemother       Date:  2018 Jan-Dec

6.  Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.

Authors:  Youcef Mehellou; Rocco Valente; Huw Mottram; Elisabeth Walsby; Kenneth I Mills; Jan Balzarini; Christopher McGuigan
Journal:  Bioorg Med Chem       Date:  2010-03-01       Impact factor: 3.641

7.  Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.

Authors:  Martin S Davey; Roshni Malde; Rory C Mykura; Alfie T Baker; Taher E Taher; Cécile S Le Duff; Benjamin E Willcox; Youcef Mehellou
Journal:  J Med Chem       Date:  2018-02-23       Impact factor: 7.446
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.