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Citation
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HERO ID
1149967
Reference Type
Journal Article
Title
Synthesis, antimalarial activity, and phototoxicity of some benzo(h)quinoline-4-methanols
Author(s)
Rice, KC
Year
1976
Is Peer Reviewed?
Yes
Journal
Journal of Medicinal Chemistry
ISSN:
0022-2623
EISSN:
1520-4804
Volume
19
Issue
7
Page Numbers
887-892
Language
English
PMID
781245
Abstract
Nine alpha-dibutylaminomethylbenzo[h]quinoline-4-methanols were synthesized from the corresponding 1-amino-naphthalenes by the following sequence: 1-aminonaphthalene leads to 1H-benz[g]indole-2,3-dione leads to benzo[h]quinoline-4-carboxylic acid leads to acid chloride leads to bromomethyl ketone leads to epoxide leads to benzo[h]quinoline-4-methanol. Several acid chlorides substituted in the 3 position reacted incompletely with ethereal diazomethane but were efficiently converted, without isolation of the intermediates, to the bromomethyl ketones by reaction with ethoxymagnesium diethylmalonate, bromination, hydrolysis, and decarboxylation. Several compounds prepared, especially alpha-dibutylaminomethyl-2-(2',4'-dimethylphenyl)-3-methyl-6-chlorobenzo[h]quinoline-4-methanol, showed significant antimalarial activity against Plasmodium berghei in infected mice but were moderately phototoxic.
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Methanol (Non-Cancer)
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Malonates
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