Abstract
5-Chloromethyl-1-methyl-2-nitroimidazole reacted efficiently with the anion derived from 5-bromoisoquinolin-1-one to give 5-bromo-2-((1-methyl-2-nitroimidazol-5-yl)methyl)isoquinolin -1-one. Biomimetic reduction effected release of the 5-bromoisoquinolin-1-one. The 2-nitroimidazol-5-ylmethyl unit thus has potential for development as a general prodrug system for selective drug delivery to hypoxic tissues.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ammonium Chloride / chemistry
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Chromatography, High Pressure Liquid
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / metabolism*
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Hypoxia
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Imidazoles / chemistry*
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Imidazoles / metabolism*
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Isoquinolines / chemistry
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Isoquinolines / metabolism*
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Oxidation-Reduction
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Palladium / chemistry
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Poly(ADP-ribose) Polymerase Inhibitors*
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Prodrugs / chemistry*
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Prodrugs / metabolism*
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Quinolones / chemistry*
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Quinolones / metabolism*
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Zinc / chemistry
Substances
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5-bromo-2-((1-methyl-2-nitroimidazol-5-yl)methyl)isoquinolin-1-one
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5-bromoisoquinolin-1-one
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Enzyme Inhibitors
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Imidazoles
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Isoquinolines
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Poly(ADP-ribose) Polymerase Inhibitors
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Prodrugs
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Quinolones
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Ammonium Chloride
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Palladium
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Zinc