Literature DB >> 6317862

Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils.

K A Watanabe, T L Su, U Reichman, N Greenberg, C Lopez, J J Fox.   

Abstract

Synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils containing a vinyl (4a), 2-halovinyl (4b-d), or ethyl substituent at C-5 was achieved. These nucleosides were found to be about a log order less active than 2'-fluoro-5-iodo-ara-C (FIAC) against HSV-1, but they are much less cytotoxic against normal human lymphocytes than FIAC. Nucleosides 4a and 4e showed good activity against HSV-1 (ED50 = 0.16 and 0.24 microM, respectively) and HSV-2 (ED50 = 0.69 and 0.65 microM) with very little cytotoxicity (ID50 greater than 100 microM).

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Year:  1984        PMID： 6317862     DOI： 10.1021/jm00367a020

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  9 in total

1.  Synthesis and biological effects of 2'-fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil.

Authors:  T C Chou; X B Kong; M P Fanucchi; Y C Cheng; K Takahashi; K A Watanabe; J J Fox
Journal:  Antimicrob Agents Chemother       Date:  1987-09       Impact factor: 5.191

2.  Selective in vitro and in vivo activities of 5-(2-haloalkyl)pyrimidine nucleoside analogs, particularly 5-(2-chloroethyl)-2'-deoxyuridine, against herpes simplex virus.

Authors:  E De Clercq; B Rosenwirth
Journal:  Antimicrob Agents Chemother       Date:  1985-08       Impact factor: 5.191

3.  Enzymology and pathogenicity in mice of a herpes simplex virus type 1 mutant resistant to 2'-fluoro-2'-deoxy-1-beta-D-arabinofuranosyl-5-iodocytosine.

Authors:  J Colacino; E Brownridge; N Greenberg; C Lopez
Journal:  Antimicrob Agents Chemother       Date:  1986-05       Impact factor: 5.191

4.  Synthesis and antiviral evaluation of 2',2',3',3'-tetrafluoro nucleoside analogs.

Authors:  Ozkan Sari; Leda Bassit; Christina Gavegnano; Tamara R McBrayer; Louise McCormick; Bryan Cox; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Tetrahedron Lett       Date:  2017-01-04       Impact factor: 2.415

5.  Semiautomated radiosynthesis and biological evaluation of [18F]FEAU: a novel PET imaging agent for HSV1-tk/sr39tk reporter gene expression.

Authors:  Frederick T Chin; Mohammed Namavari; Jelena Levi; Murugesan Subbarayan; Pritha Ray; Xiaoyuan Chen; Sanjiv S Gambhir
Journal:  Mol Imaging Biol       Date:  2007-12-22       Impact factor: 3.488

6.  An investigation on stereospecific fluorination at the 2'-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2'-deoxy-2'-[(18)F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil.

Authors:  Nashaat Turkman; Vincenzo Paolillo; Juri G Gelovani; Mian M Alauddin
Journal:  Tetrahedron       Date:  2012-12-16       Impact factor: 2.457

7.  Fluorinated Nucleosides: Synthesis and Biological Implication.

Authors:  Peng Liu; Ashoke Sharon; Chung K Chu
Journal:  J Fluor Chem       Date:  2008-09       Impact factor: 2.050

8.  Evaluation of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-beta-L: -arabinofuranosyluracil ([18F]-L: -FMAU) as a PET imaging agent for cellular proliferation: comparison with [18F]-D: -FMAU and [18F]FLT.

Authors:  Ryuichi Nishii; Andrei Y Volgin; Osama Mawlawi; Uday Mukhopadhyay; Ashutosh Pal; William Bornmann; Juri G Gelovani; Mian M Alauddin
Journal:  Eur J Nucl Med Mol Imaging       Date:  2007-12-04       Impact factor: 9.236

9.  In vivo evaluation of 2'-deoxy-2'-[(18)F]fluoro-5-iodo-1-beta-D-arabinofuranosyluracil ([18F]FIAU) and 2'-deoxy-2'-[18F]fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil ([18F]FEAU) as markers for suicide gene expression.

Authors:  Mian M Alauddin; Antranic Shahinian; Ryan Park; Michel Tohme; John D Fissekis; Peter S Conti
Journal:  Eur J Nucl Med Mol Imaging       Date:  2007-01-06       Impact factor: 10.057
  9 in total

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