Synthesis and antitumor activity of 2-. beta. -D-ribofuranosylselenazole-4-carboxamide and related derivatives
Journal Article
·
· J. Med. Chem.; (United States)
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 ..cap 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.
- Research Organization:
- Oak Ridge National Lab., TN
- OSTI ID:
- 5312519
- Journal Information:
- J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 26:3; ISSN JMCMA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
550600 -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ANIMALS
BODY
CARCINOMAS
CHEMICAL PREPARATION
CHEMOTHERAPY
DISEASES
FURANS
HETEROCYCLIC COMPOUNDS
LUNGS
MAMMALS
MICE
NEOPLASMS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
ORGANS
RESPIRATORY SYSTEM
RODENTS
SELENIUM COMPOUNDS
SYNTHESIS
THERAPY
VERTEBRATES
400201* -- Chemical & Physicochemical Properties
550600 -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ANIMALS
BODY
CARCINOMAS
CHEMICAL PREPARATION
CHEMOTHERAPY
DISEASES
FURANS
HETEROCYCLIC COMPOUNDS
LUNGS
MAMMALS
MICE
NEOPLASMS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
ORGANS
RESPIRATORY SYSTEM
RODENTS
SELENIUM COMPOUNDS
SYNTHESIS
THERAPY
VERTEBRATES