Literature DB >> 6827564

Synthesis and antitumor activity of 2-beta-D-ribofuranosylselenazole-4- carboxamide and related derivatives.

P C Srivastava, R K Robins.   

Abstract

Treatment of 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl-1-carbonitrile with hydrogen selenide provided 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonselenoamide (3). Compound 3 was treated with ethyl bromopyruvate to provide ethyl 2-(2,3,5-tri-O-benzoyl-D-ribofuranosyl)selenazole-4-carboxylates, which after ammonolysis were converted to 2-beta-D-ribofuranosylselenazole-4-carboxamide (6) and its alpha-analogue 7, respectively. Acetylation of nucleoside 6 provided 2-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)selenazole-4-carboxamide, and phosphorylation of 6 provided the corresponding 5'-phosphate 9. Compounds 6 and 9 were found to be cytotoxic toward P388 and L1210 cells in culture and effective against Lewis lung carcinoma in mice.

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Year:  1983        PMID： 6827564     DOI： 10.1021/jm00357a024

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


  14 in total

1.  Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds.

Authors:  E De Clercq; M Cools; J Balzarini; R Snoeck; G Andrei; M Hosoya; S Shigeta; T Ueda; N Minakawa; A Matsuda
Journal:  Antimicrob Agents Chemother       Date:  1991-04       Impact factor: 5.191

2.  Broad-spectrum antiviral activity of 2-beta-D-ribofuranosylselenazole-4-carboxamide, a new antiviral agent.

Authors:  J J Kirsi; J A North; P A McKernan; B K Murray; P G Canonico; J W Huggins; P C Srivastava; R K Robins
Journal:  Antimicrob Agents Chemother       Date:  1983-09       Impact factor: 5.191

Review 3.  Isoselenocyanates: a powerful tool for the synthesis of selenium-containing heterocycles.

Authors:  Dinesh Ramesh Garud; Mamoru Koketsu; Hideharu Ishihara
Journal:  Molecules       Date:  2007-03-17       Impact factor: 4.411

4.  Synergistic antiviral effects of ribavirin and the C-nucleoside analogs tiazofurin and selenazofurin against togaviruses, bunyaviruses, and arenaviruses.

Authors:  J W Huggins; R K Robins; P G Canonico
Journal:  Antimicrob Agents Chemother       Date:  1984-10       Impact factor: 5.191

5.  Broad-spectrum synergistic antiviral activity of selenazofurin and ribavirin.

Authors:  J J Kirsi; P A McKernan; N J Burns; J A North; B K Murray; R K Robins
Journal:  Antimicrob Agents Chemother       Date:  1984-10       Impact factor: 5.191

6.  Effects of selenazofurin and ribavirin and their 5'-triphosphates on replicative functions of influenza A and B viruses.

Authors:  S K Wray; R H Smith; B E Gilbert; V Knight
Journal:  Antimicrob Agents Chemother       Date:  1986-01       Impact factor: 5.191

7.  Modulation of nicotinamide adenine dinucleotide and poly(adenosine diphosphoribose) metabolism by the synthetic "C" nucleoside analogs, tiazofurin and selenazofurin. A new strategy for cancer chemotherapy.

Authors:  N A Berger; S J Berger; D M Catino; S J Petzold; R K Robins
Journal:  J Clin Invest       Date:  1985-02       Impact factor: 14.808

8.  Activity of selenazofurin against influenza A and B viruses in vitro.

Authors:  R W Sidwell; J H Huffman; E W Call; H Alaghamandan; P D Cook; R K Robins
Journal:  Antimicrob Agents Chemother       Date:  1985-09       Impact factor: 5.191

9.  Tris(1,10-phenanthroline-κN,N')zinc(II) chloride 2-phenyl-4-selenazole-5-car-box-yl-ate decahydrate.

Authors:  Jin-Bei Shen; Xin Lv; Ji-Fei Chen; Yu-Feng Zhou; Guo-Liang Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-15

10.  An enzymatic route to selenazolines.

Authors:  Jesko Koehnke; Falk Morawitz; Andrew F Bent; Wael E Houssen; Sally L Shirran; Matthew A Fuszard; Iain A Smellie; Catherine H Botting; Margaret C M Smith; Marcel Jaspars; James H Naismith
Journal:  Chembiochem       Date:  2013-02-18       Impact factor: 3.164
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