Fluorinated Analogues of the p17/p24 Sequence Incorporating 3-fluoro and 3,3-difluoro Phenylalanines as Potential Inhibitors of HIV Protease-Reference-Cited by-同舟云学术

Fluorinated Analogues of the p17/p24 Sequence Incorporating 3-fluoro and 3,3-difluoro Phenylalanines as Potential Inhibitors of HIV Protease

Published:1994-12 Issue:6 Volume:5 Page:372-379
ISSN:2040-2066
Container-title:Antiviral Chemistry and Chemotherapy
language:en
Short-container-title:Antivir Chem Chemother

Author:

Frogier P. R. T.¹,Tran T. T.¹,Viani S.¹,Condom R.¹,Guedj R.¹

Affiliation:

1. Laboratoire de Chimie Bio-Organique, Faculté des Sciences, UNSA, BP 71, 06108 Nice, Cedex-2, France

Abstract

The synthesis and activity of a series of fluorinated peptide analogues of the p17/p24 sequence incorporating 3-fluoro and 3,3-difluoro phenylananines at the P1 position of the scissile bond are described. It was hoped that these might act as potent inhibitors of HIV protease. In fact, none of the compounds studied displayed any anti-HIV activity in vitro. This may be attributed to poor cell penetration of the compounds and metabolic cleavage of their peptide bonds.

Publisher

SAGE Publications

Link

http://journals.sagepub.com/doi/pdf/10.1177/095632029400500604

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1. Asymmetric synthesis of β,β-difluoroamino acids via cross-coupling and Strecker reactions;Tetrahedron;2008-02

2. Approaches to the Design of Effective HIV-1 Protease Inhibitors;Current Medicinal Chemistry;2000-04-01

3. A New Method for the Synthesis of α,α-Difluoro-β-hydroxy Esters through the Enolization of S-tert-Butyl Difluoroethanethioate;The Journal of Organic Chemistry;1997-09-01

4. Fluorinated peptides incorporating a 4-fluoroproline residue as potential inhibitors of HIV protease;Journal of Fluorine Chemistry;1997-05

5. Methods for the synthesis of gem-difluoromethylene compounds;Tetrahedron;1996-06