Synthesis and structure-activity relationships of 3-aminobenzophenones as antimitotic agents

Jing Ping Liou, Jang Yang Chang, Chun Wei Chang, Chi Yen Chang, Neeraj Mahindroo, Fu Ming Kuo, Hsing Pang Hsieh

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105 Citations (Scopus)


A new series of 3-aminobenzophenone compounds as potent inhibitors of tubulin polymerization was discovered based on the mimic of the aminocombretastatin molecular skeleton. Lead compounds 5 and 11, with alkoxy groups at the C-4 position of B-ring, were potent cytotoxic agents and inhibitors of tubulin polymerization through the binding to the colchicine-binding site of tubulin. The corresponding antitubulin activities of 5 and 11 were similar to or greater than combretastatin A-4 and AVE-8063. Replacement of the methoxy group with a chloro group in the B ring of aminobenzopheneones (3, 8, and 9) caused drastic decrease in cytotoxic and antitubulin activity except in compounds 4 and 10, which could result from a unique alignment between chloro and amino groups located at the para position to each other. SAR information revealed that introduction of an amino group at the C-3 position in B ring of benzophenones, in addition to a methoxy group at the C-4 position, plays an important role for maximal cytotoxicity.

Original languageEnglish
Pages (from-to)2897-2905
Number of pages9
JournalJournal of Medicinal Chemistry
Issue number11
Publication statusPublished - May 20 2004
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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