Literature DB >> 34321697

Synthesis and anti-HIV activity of 5-haloethynyl and 5-(1,2-dihalo)vinyl analogues of AZT and FLT.

Nicolas Joubert1, Franck Amblard1, Kimberly L Rapp2, Raymond F Schinazi2, Luigi A Agrofoglio1.   

Abstract

In this paper, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleoside analogues of the anti-HIV AZT, and FLT drugs. The key step of those syntheses is a Pd(0) cross-coupling at C5 position under Sonogashira conditions. Finally, based on their in vitro anti-HIV activities and their cytotoxicity on PBM, CEM, and VERO cell lines, the best compounds were the 2',3'-dideoxy-3'-fluoro-5-(bromo-2-iodo)vinyluridine (10b, EC50 of 0.6 μM), and the 3'-azido-2',3'-dideoxy-5-(bromo-2-iodo)vinyluridine (16b, EC50 of 1.1 μM).

Entities:  

Year:  2008        PMID： 34321697      PMCID： PMC8315093          DOI： 10.1016/j.tet.2008.02.079

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  23 in total

Review 1.  The synthesis and antiviral properties of acyclic nucleoside analogues with a phosphonomethoxy fragment in the side chain.

Authors:  A Khandazhinskaya; M Yasko; E Shirokova
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

2.  3'-Deoxy-3'-fluorothymidine, a new selective inhibitor of DNA-synthesis.

Authors:  P Langen; G Etzold; R Hintsche; G Kowollik
Journal:  Acta Biol Med Ger       Date:  1969

3.  Activities of 3'-azido-3'-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1.

Authors:  R F Schinazi; J P Sommadossi; V Saalmann; D L Cannon; M Y Xie; G C Hart; G A Smith; E F Hahn
Journal:  Antimicrob Agents Chemother       Date:  1990-06       Impact factor: 5.191

Review 4.  Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.

Authors:  E De Clercq
Journal:  Clin Microbiol Rev       Date:  2001-04       Impact factor: 26.132

Review 5.  Antiviral properties of deazaadenine nucleoside derivatives.

Authors:  S Vittori; D Dal Ben; C Lambertucci; G Marucci; R Volpini; G Cristalli
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

6.  Reaction of alkynes with iodine monochloride revisited.

Authors:  Fabio Bellina; Francesca Colzi; Luisa Mannina; Renzo Rossi; Stephane Viel
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

7.  Newly synthesized L-enantiomers of 3'-fluoro-modified beta-2'-deoxyribonucleoside 5'-triphosphates inhibit hepatitis B DNA polymerases but not the five cellular DNA polymerases alpha, beta, gamma, delta, and epsilon nor HIV-1 reverse transcriptase.

Authors:  M von Janta-Lipinski; B Costisella; H Ochs; U Hübscher; P Hafkemeyer; E Matthes
Journal:  J Med Chem       Date:  1998-06-04       Impact factor: 7.446

8.  Synthesis and biological activities of novel 5-(2-acylethynyl)uracils.

Authors:  N G Kundu; B Das; C P Spears; A Majumdar; S I Kang
Journal:  J Med Chem       Date:  1990-07       Impact factor: 7.446

9.  3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro.

Authors:  H Mitsuya; K J Weinhold; P A Furman; M H St Clair; S N Lehrman; R C Gallo; D Bolognesi; D W Barry; S Broder
Journal:  Proc Natl Acad Sci U S A       Date:  1985-10       Impact factor: 11.205

10.  Comparisons of anti-human immunodeficiency virus activities, cellular transport, and plasma and intracellular pharmacokinetics of 3'-fluoro-3'-deoxythymidine and 3'-azido-3'-deoxythymidine.

Authors:  X B Kong; Q Y Zhu; P M Vidal; K A Watanabe; B Polsky; D Armstrong; M Ostrander; S A Lang; E Muchmore; T C Chou
Journal:  Antimicrob Agents Chemother       Date:  1992-04       Impact factor: 5.191
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  1 in total

1.  One-pot three component synthesis of 5-allyl-1,2,3-triazoles using copper(i) acetylides.

Authors:  Parigi Raghavendar Reddy; Lianji Cui; Jae-Sang Ryu
Journal:  RSC Adv       Date:  2018-01-12       Impact factor: 4.036
  1 in total

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