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Synthesis and evaluation of novel electrophilic nitrofuran carboxamides and carboxylates as radiosensitizers and bioreductively activated cytotoxins

Journal Article · · Journal of Medicinal Chemistry; (USA)
DOI:https://doi.org/10.1021/jm00171a027· OSTI ID:6420086
; ; ; ; ; ; ;  [1]
  1. Medical Research Council Radiobiology Unit, Didcot, Oxon (England)
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A series of 5-nitrofuran-2- and 3-carboxamides bearing alkylating side-chains has been synthesized and tested for their ability to radiosensitize selectively hypoxic Chinese hamster cells (V79) to the lethal effects of ionizing radiation and also for their ability to act directly and selectively as cytotoxic drugs on hypoxic V79 cells. The compounds were extremely efficient radiosensitizers of such cells in vitro and were more efficient than known nitroimidazoles of similar type. Their efficiencies as radiosensitizers correlated with their high electron affinity (E7)1 as measured by pulse-radiolysis. However the compounds showed little radiosensitizing activity towards KHT sarcomas in C3H mice. The compounds in this series of nitrofurans were generally more toxic towards hypoxic cells than towards oxic cells in vitro but were less effective upon the basis of a differential effect than were similar nitroimidazoles reported previously.

OSTI ID:
6420086
Journal Information:
Journal of Medicinal Chemistry; (USA), Journal Name: Journal of Medicinal Chemistry; (USA) Vol. 33:9; ISSN JMCMA; ISSN 0022-2623
Country of Publication:
United States
Language:
English

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Related Subjects

550603 -- Medicine-- External Radiation in Therapy-- (1980-)
560120* -- Radiation Effects on Biochemicals
Cells
& Tissue Culture
62 RADIOLOGY AND NUCLEAR MEDICINE
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMIDES
ANIMAL CELLS
ANIMALS
BODY
CHEMICAL PREPARATION
CHO CELLS
DISEASES
DRUGS
EVALUATION
EXPERIMENTAL NEOPLASMS
LUNGS
MAMMALS
MICE
NEOPLASMS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANS
RADIOSENSITIVITY EFFECTS
RADIOSENSITIZERS
RESPIRATORY SYSTEM
RODENTS
SARCOMAS
STRUCTURE-ACTIVITY RELATIONSHIPS
SYNTHESIS
VERTEBRATES