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

Mehellou, Youcef ORCID: https://orcid.org/0000-0001-5720-8513, McGuigan, Christopher ORCID: https://orcid.org/0000-0001-8409-710X, Brancale, Andrea ORCID: https://orcid.org/0000-0002-9728-3419 and Balzarini, J. 2007. Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate "ProTide' derivatives. Biorganic and Medicinal Chemistry Letters 17 (13) , pp. 3666-3669. 10.1016/j.bmcl.2007.04.043

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Pharmacy Research Institutes & Centres > Systems Immunity Research Institute (SIURI)
Subjects:	R Medicine > R Medicine (General)
Uncontrolled Keywords:	HIV; Phosphoramidates; ddU; ProTide
Publisher:	Elsevier
ISSN:	0960-894X
Date of Acceptance:	15 April 2007
Last Modified:	05 Jan 2024 05:56
URI:	https://orca.cardiff.ac.uk/id/eprint/6650

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