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Potential radiosensitizing agents. 4. 2-Nitroimidazole nucleosides

Journal Article · · J. Med. Chem.; (United States)
DOI:https://doi.org/10.1021/jm00353a013· OSTI ID:6163469
; ;

A series of 2-nitroimidazole nucleoside analogues has been synthesized as potential radiosensitizers in an effort to reduce neurotoxicity and increase therapeutic efficacy. The 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl and glucothiopyranosyl analogues of 2-nitroimidazole were synthesized by condensation in the presence of stannic chloride and mercuric cyanide. The deacetylation of these esters was carried out with sodium methoxide at 0 degree C. Condensation of the trimethylsilyl derivative of 2-nitroimidazole with methyl 2-deoxy-2-chloro-4,7,8,9-tetra-O-acetyl-N-acetyl-alpha-D-neuraminate was achieved in the presence of mercuric bromide. These agents were tested for cytotoxicity and radiosensitization in vitro against Chinese hamster (V-79) cells under oxic and hypoxic conditions. The thioglucose and sialic acid analogues were found to be active radiosensitizers.

Research Organization:
Department of Pharmacology, Tulane University School of Medicine, New Orleans, Louisiana
OSTI ID:
6163469
Journal Information:
J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 25:11; ISSN JMCMA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400300 -- Organic Chemistry-- (-1987)
550603 -- Medicine-- External Radiation in Therapy-- (1980-)
560121* -- Radiation Effects on Cells-- External Source-- (-1987)
62 RADIOLOGY AND NUCLEAR MEDICINE
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANOXIA
AZOLES
CELL CULTURES
CHEMICAL PREPARATION
DRUGS
HETEROCYCLIC COMPOUNDS
IMIDAZOLES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
RADIOSENSITIVITY
RADIOSENSITIVITY EFFECTS
RADIOSENSITIZERS
SYNTHESIS
TOXICITY