- Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives
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A series of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidines bearing cationic side chains were prepared from aminoanthraquinones. The perimidines were prepared from 1-aminoanthraquinone by initial condensation with urea or dimethylacetamide. A series of 2-, 4-, 8-, and 11-carboxy derivatives of the dibenzisoquinolines were prepared from aminoanthraquinonecarboxylic acids. The cationic derivatives were prepared from these via amide, amine, or methylene linkers to study the effects of side chain positioning on biological activity. Within the series of carboxamide-linked compounds, the order of increasing cytotoxicity was 8- 4- 2- 11-. The 2- and 4-carboxamides showed substantial growth delays against in vivo subcutaneous colon 38 tumors in mice, but the 11-carboxamide had curative activity in this refractory model and is being investigated further.
- Bu,Deady,Finlay,Baguley,Denny
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p. 2004 - 2014
(2007/10/03)
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- Synthesis of Naphthindol-6(2H)-one Derivatives and Their Fluorescence Properties
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Highly fluorescent 1-phenylnaphthindol-6(2H)-one (3b) and its 7-chloro and 7-amino derivatives were synthesized by reaction of 1-aminoanthraquinone with benzyl chloride in KOH-DMSO system, followed by treatment with aluminium chloride.The compound 3b was easily N-alkylated with various alkyl halides in KOH-DMSO system.The fluorescence quantum yields (Φf) of naphthindol-6(2H)-one derivatives 3 were high (0.5-0.7), except for 7-amino derivatives which did not fluoresce.The Φf of 7-chloro derivative (3d) was strongly dependent on solvent: 0.37 in ethanol; 0.02 in acetonitrile; 0 in benzene.The compounds 3 were demonstrated to be efficient laser dyes for 500-550 nm region.
- Arai, Sadao,Yamauchi, Shigeaki,Moriya, Yuriko,Tanaka, Tei-ichi,Yamazaki, Yoko,et al.
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p. 3417 - 3421
(2007/10/02)
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- Process for the production of nitro derivatives of aromatic compounds
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Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.
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