Synthesis of 2-aryl-6-methyl-5-nitroquinoline derivatives as potential prodrug systems for reductive activation |
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Authors: | Gavin D. Couch Richard J. Knox |
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Affiliation: | a School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK b Morvus Technology Ltd, Porton Down Science Park, Salisbury, Wiltshire SP4 0JQ, UK |
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Abstract: | A range of novel 2-aryl-5-nitroquinolines have been synthesised as potential prodrug systems for bioreductive activation. Thus 5-nitroquinoline underwent vicarious nucleophilic substitution at C-6 with bromoform anion to give, after hydrolysis and reduction, the quinoline-6-methanol. Introduction of chlorine at C-2 was followed by palladium-catalysed Suzuki coupling to install the 2-aryl substituent. A fluorescent model ‘drug’, 7-hydroxy-4-methylcoumarin was coupled to the 6-hydroxymethyl group, and its fragmentation upon reduction of the nitro group was investigated. |
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