Literature DB >> 20183600

Synthesis and antiviral activity of purine 2',3'-dideoxy-2',3'-difluoro-D-arabinofuranosyl nucleosides.

Grigorii G Sivets1, Elena N Kalinichenko, Igor A Mikhailopulo, Mervi A Detorio, Tami R McBrayer, Tony Whitaker, Raymond F Schinazi.   

Abstract

9-(2',3'-Dideoxy-2',3'-difluoro-beta-D-arabinofuranosyl)adenine (20), 2-chloro-9-(2',3'-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)adenine (22), as well as their respective alpha-anomers 21 and 23, were synthesized by the nucleobase anion glycosylation of intermediate 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-alpha-D-arabinofuranosyl bromide (13) starting from methyl 5-O-benzyl-3-deoxy-3-fluoro-alpha-D-ribofuranoside (3) and methyl 5-O-benzoyl-alpha-D-xylofuranoside (10). These compounds were evaluated as potential inhibitors of HIV-1 and hepatitis C virus in human PBM and Huh-7 Replicon cells, respectively. The adenosine analog 20 demonstrated potent activity against HIV-1 in primary human lymphocytes with no apparent cytotoxicity. Conformation of pentofuranose ring of nucleoside 20 in solution was studied by PSEUROT calculations.

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Year:  2009        PMID： 20183600      PMCID： PMC7732020          DOI： 10.1080/15257770903053979

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN： 1525-7770            Impact factor:   1.381


  18 in total

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Authors:  E De Clercq
Journal:  AIDS Res Hum Retroviruses       Date:  1992-02       Impact factor: 2.205

2.  Oligonucleotides containing 9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties.

Authors:  T Tennilä; E Azhayeva; J Vepsäläinen; R Laatikainen; A Azhayev; I A Mikhailopulo
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2000 Oct-Dec       Impact factor: 1.381

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

4.  Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.

Authors:  Lieven J Stuyver; Stefania Lostia; Marjorie Adams; Judy S Mathew; Balakrishna S Pai; Jason Grier; Phillip M Tharnish; Yongseok Choi; Youhoon Chong; Hyunah Choo; Chung K Chu; Michael J Otto; Raymond F Schinazi
Journal:  Antimicrob Agents Chemother       Date:  2002-12       Impact factor: 5.191

5.  Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).

Authors:  J A Martin; D J Bushnell; I B Duncan; S J Dunsdon; M J Hall; P J Machin; J H Merrett; K E Parkes; N A Roberts; G J Thomas
Journal:  J Med Chem       Date:  1990-08       Impact factor: 7.446

6.  Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.

Authors:  Junxing Shi; Jinfa Du; Tianwei Ma; Krzysztof W Pankiewicz; Steven E Patterson; Phillip M Tharnish; Tamara R McBrayer; Lieven J Stuyver; Michael J Otto; Chung K Chu; Raymond F Schinazi; Kyoichi A Watanabe
Journal:  Bioorg Med Chem       Date:  2005-03-01       Impact factor: 3.641

7.  Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication.

Authors:  Jeremy L Clark; Laurent Hollecker; J Christian Mason; Lieven J Stuyver; Phillip M Tharnish; Stefania Lostia; Tamara R McBrayer; Raymond F Schinazi; Kyoichi A Watanabe; Michael J Otto; Phillip A Furman; Wojciech J Stec; Steven E Patterson; Krzysztof W Pankiewicz
Journal:  J Med Chem       Date:  2005-08-25       Impact factor: 7.446

8.  2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides: synthesis, stereospecificity, some chemical transformations, and conformational analysis.

Authors:  Igor A Mikhailopulo; Tamara I Pricota; Grigorii G Sivets; Cornelis Altona
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

9.  Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.

Authors:  P Herdewijn; R Pauwels; M Baba; J Balzarini; E De Clercq
Journal:  J Med Chem       Date:  1987-11       Impact factor: 7.446

10.  Comprehensive structural studies of 2',3'-difluorinated nucleosides: comparison of theory, solution, and solid state.

Authors:  Joseph J Barchi; Rajeshri G Karki; Marc C Nicklaus; Maqbool A Siddiqui; Clifford George; Igor A Mikhailopulo; Victor E Marquez
Journal:  J Am Chem Soc       Date:  2008-06-18       Impact factor: 15.419
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