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Synthesis and cancer cell cytotoxicity of substituted xanthenes.

Abstract：

:A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9 g ([N,N-diethyl]-9-hydroxy-9-(3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC(50) values ranging from 36 to 50 microM across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e.g., the incorporation of a 7-fluoro substituent to 9 g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Giri R,Goodell JR,Xing C,Benoit A,Kaur H,Hiasa H,Ferguson DM

doi

10.1016/j.bmc.2010.01.018

subject

Has Abstract

pub_date

2010-02-15 00:00:00

pages

1456-63

issue

4

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00039-8

journal_volume

18

pub_type

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