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The synthesis of aryl 4‐nitro‐5‐imidazolyl sulfone radiation sensitizers sterically protected against glutathione reaction
Author(s) -
Egolf Roger A.,
Heindel Ned D.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280307
Subject(s) - chemistry , sulfone , aryl , steric effects , nitro , glutathione , nitro compound , reactivity (psychology) , medicinal chemistry , stereochemistry , organic chemistry , enzyme , medicine , alkyl , alternative medicine , pathology
2,6‐Disubstituted aryl 1‐methyl‐4‐nitro‐5‐imidazolyl sulfones 4 and aryl 1‐neopentyl‐2‐ tert ‐butyl‐4‐nitro‐5‐imidazolyl sulfones 10 have been synthesized and tested as radiation sensitizers of hypoxic carcinoma cells. These sterically crowded imidazoles show decreased displacement reactivity with glutathione at C‐5, a major metabolic reaction known to deplete effective plasma drug levels in traditional aryl imidazolyl sulfone radiation sensitizers.