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

Autor:	Pen Fong Yeh, Hsu Shan Huang, Hui Fen Chiu, Chun Lung Yuan
Rok vydání:	2004
Předmět:	Cisplatin Mitoxantrone Chemistry Stereochemistry Organic Chemistry medicine.disease Biochemistry Combinatorial chemistry Catalysis In vitro Inorganic Chemistry Glioma Drug Discovery medicine Cytotoxic T cell Structure based Potency Physical and Theoretical Chemistry Amination medicine.drug
Zdroj:	Helvetica Chimica Acta. 87:999-1006
ISSN:	1522-2675 0018-019X
DOI:	10.1002/hlca.200490093
Popis:	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.
Databáze:	OpenAIRE
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