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

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...

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Published inJournal of medicinal chemistry Vol. 26; no. 3; pp. 445 - 448
Main Authors Srivastava, Prem C, Robins, Roland K
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.03.1983
Subjects
Animals
Antineoplastic Agents
Chemical Phenomena
Chemistry
Lung Neoplasms - drug therapy
Mice
Ribonucleosides - chemical synthesis
Ribonucleosides - therapeutic use
Selenium
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Summary: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.
Bibliography:istex:0C67D102D4BF6BA5094F0D935A9A98AC80598A5B
ark:/67375/TPS-2Q0H8PW5-D
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-2623
1520-4804
DOI:10.1021/jm00357a024