Synthesis and in vitro antiproliferative activity of new phenylaminoisoquinolinequinones against cancer cell lines

A variety of phenylaminoisoquinolinequinones were synthesized and tested for their antiproliferative activity against three human-tumor derived cancer cell lines. The new aminoquinones were prepared from 4-methoxycarbonyl-3-methylisoquinoline-5,8-quinone (1) via acid-induced amination and brominatio...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-01, Vol.18 (1), p.721-734
Main Authors: Delgado, Virginia, Ibacache, Andrea, Arancibia, Verónica, Theoduloz, Cristina, Valderrama, Jaime A
Format: Article
Language:English
Subjects:
Amination
Aniline Compounds - chemical synthesis
Aniline Compounds - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
antiproliferative activity
Benzaldehydes - chemistry
Cancer
Cell Line, Tumor
Cell Proliferation - drug effects
Chromatography
Crotonates - chemistry
Drug Screening Assays, Antitumor
half-wave potential
Halogenation
Humans
Inhibitory Concentration 50
Isoquinolines - chemistry
Nitrogen
NMR
Nuclear magnetic resonance
Oxidation-Reduction
phenylaminoisoquinoline-5,8-quinones
Quinolones - chemical synthesis
Quinolones - pharmacology
regioselectivity
SAR analysis
Structure-Activity Relationship
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Summary:A variety of phenylaminoisoquinolinequinones were synthesized and tested for their antiproliferative activity against three human-tumor derived cancer cell lines. The new aminoquinones were prepared from 4-methoxycarbonyl-3-methylisoquinoline-5,8-quinone (1) via acid-induced amination and bromination reactions. Remarkable differences in antiproliferative activity were observed depending upon the location and donor capacity of the substituted phenylamino group at the quinone nucleus. The effect of the substituents on the biological activity is discussed in terms of the donor-acceptor interactions which were evaluated through the redox properties of the aminoquinones.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18010721