Literature DB >> 6292837

Synthesis and biological properties of 2'-deoxy-5-vinyluridine and 2'deoxy-5-vinylcytidine.

S G Rahim, M J Duggan, R T Walker, A S Jones, R L Dyer, J Balzarini, E De Clercq.   

Abstract

Rapid and efficient syntheses for the preparation of 2'-deoxy-5-vinyluridine and 2'-deoxy-5-vinylcytidine are described starting from nucleoside precursors. Contrary to some previous reports, 2-deoxy-5-vinyluridine has be found to be quite stable under normal laboratory conditions but when tested in animals shows neither toxicity nor anti-leukemic (L1210 cells) or anti-parasitic (Plasmodium berghei) activity. 2'-Deoxy-5-vinylcytidine appears to polymerise readily. It is much less toxic to cell cultures than 2'-deoxy-5'vinyluridine but is almost as active against herpes virus replication (ID50:0.2 microgram/ml) for both type 1 and type 2 herpes virus (selectivity index:225).

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Year:  1982        PMID: 6292837      PMCID: PMC320871          DOI: 10.1093/nar/10.17.5285

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN: 0305-1048            Impact factor:   16.971


  13 in total

1.  Synthesis of 5-vinyluridine and 5-vinyl-2'-deoxyuridine as new pyrimidine nucleoside analogs.

Authors:  R A Sharma; M Bobek
Journal:  J Org Chem       Date:  1975-08-08       Impact factor: 4.354

2.  Selective inhibition of the replication of herpes simplex virus by 5-halogenated analogues of deoxycytidine.

Authors:  I Schildkraut; G M Cooper; S Greer
Journal:  Mol Pharmacol       Date:  1975-03       Impact factor: 4.436

3.  Letter: Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates.

Authors:  D E Bergstrom; J L Ruth
Journal:  J Am Chem Soc       Date:  1976-03-17       Impact factor: 15.419

4.  Incorporation of 5-substituted uracil derivatives into nucleic acids. II. Incorporation of 5-vinyluracil into the DNA of Escherichia coli.

Authors:  E T Chelton; C H Evans; A S Jones; R T Walker
Journal:  Biochim Biophys Acta       Date:  1973-06-08

5.  The chemistry of some 5-(2-hydroxyalkyl)uracil derivatives and a synthesis of 5-vinyluracil.

Authors:  J D Fissekis; F Sweet
Journal:  J Org Chem       Date:  1973-01-26       Impact factor: 4.354

6.  The synthesis and properties of some 5-substituted uracil derivatives.

Authors:  R T Walker; A S Jones; S G Rahim; P Serafinowski; E De Clercq
Journal:  Nucleic Acids Symp Ser       Date:  1981

7.  Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2'-deoxyuridines on mouse leukemia L1210 cell growth.

Authors:  E De Clercq; J Balzarini; P F Torrence; M P Mertes; C L Schmidt; D Shugar; P J Barr; A S Jones; G Verhelst; R T Walker
Journal:  Mol Pharmacol       Date:  1981-03       Impact factor: 4.436

8.  (E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent.

Authors:  E De Clercq; J Descamps; P De Somer; P J Barr; A S Jones; R T Walker
Journal:  Proc Natl Acad Sci U S A       Date:  1979-06       Impact factor: 11.205

9.  Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2'-deoxycytidines.

Authors:  E De Clercq; J Balzarini; J Descamps; G F Huang; P F Torrence; D E Bergstrom; A S Jones; P Serafinowski; G Verhelst; R T Walker
Journal:  Mol Pharmacol       Date:  1982-01       Impact factor: 4.436

10.  Antiviral action and cellular toxicity of four thymidine analogues: 5-ethyl-,5-vinyl-, 5-propyl-, and 5-allyl-2'- deoxyuridine.

Authors:  Y C Cheng; B A Domin; R A Sharma; M Bobek
Journal:  Antimicrob Agents Chemother       Date:  1976-07       Impact factor: 5.191

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  2 in total

Review 1.  Structure-activity relationships and conformational features of antiherpetic pyrimidine and purine nucleoside analogues. A review.

Authors:  T Kulikowski
Journal:  Pharm World Sci       Date:  1994-04-15

2.  Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues.

Authors:  Lucie Brulikova; Jan Hlavac
Journal:  Beilstein J Org Chem       Date:  2011-05-26       Impact factor: 2.883

  2 in total

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