Structure-Based Design and Synthesis of Regioisomeric Disubstituted Aminoanthraquinone Derivatives as Potential Anticancer Agents

Hsu Shan Huang, Hui Fen Chiu, Pen Fong Yeh, Chun Lung Yuan

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16 Citations (Scopus)


Continuing our ongoing studies on cytotoxic substances, we report the synthesis and cytotoxic properties of a series of symmetric 1,5-diamino-9,10-anthraquinones with potentially bioreducible groups. Symmetric amination of 1,5-dichloro-9,10-anthraquinone with the appropriate primary amines in the presence of DMF furnished the structurally related aminoanthraquinone analogs 1-19. Their in vitro cytotoxic activity was evaluated using rat glioma C6 cells, human hepatoma G2 cells, and 2.2.15 cells. Several compounds exhibited very high antitumor activities in these assays. Compound 4 efficiently inhibited C6 cells, human hepatoma G2 cells, and 2.2.15 cells, as determined by means of the XTT colorimetric assay. The antiproliferative activity of 4 was markedly enhanced, reaching a potency comparable to those of the powerful anticancer agents mitoxantrone, adriamycin, and cisplatin. Biological evaluations and structure/activity relationships within this class of novel aminoanthraquinones are discussed.

Original languageEnglish
Pages (from-to)999-1006
Number of pages8
JournalHelvetica Chimica Acta
Issue number4
Publication statusPublished - 2004
Externally publishedYes


ASJC Scopus subject areas

  • Chemistry(all)

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