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PHOTOLYTIC REARRANGEMENT OF METRONIDAZOLE TO 1‐HYDROXYETHYL‐2‐METHYL‐4‐HYDROXYIMINO‐5‐OXO‐IMIDAZOLE AND THE FORMATION OF COPPER COMPLEXES OF THESE COMPOUNDS
Author(s) -
Wilkins Brian J.,
Moore Douglas E.
Publication year - 1988
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1988.tb08834.x
Subject(s) - metronidazole , chemistry , imidazole , chelation , denticity , copper , photodissociation , medicinal chemistry , methanol , stereochemistry , photochemistry , organic chemistry , antibiotics , crystal structure , biochemistry
— A labile intermediate in the photolytic rearrangement of the antibacterial drug, metronidazole, was identified by isolating the product of photolysis of metronidazole benzoate in methanol. The intermediate, 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole, was shown to act as a bidentate chelating agent for copper(II) ions, whereas metronidazole forms a weak monodentate complex. The intermediate may be relevant to the bioactivation mechanism of metronidazole.