Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents

Jing Ping Liou, Chun Wei Chang, Jeng Shin Song, Yung Ning Yang, Ching Fang Yeh, Huan Yi Tseng, Yu Kang Lo, Yi Ling Chang, Chung Ming Chang, Hsing Pang Hsieh

Research output: Contribution to journalArticle

126 Citations (Scopus)

Abstract

A new type of inhibitor of tubulin polymerization was discovered on the basis of the combretastatin molecular skeleton. The lead compounds in this series, compounds 6 and 7, strongly inhibited tubulin polymerization in vitro and significantly arrested cells at the G2/M phase. Compounds 6 and 7 yielded 50- to 100-fold lower IC50 values than did combretastatin A-4 against Colo 205, NUGC3, and HA22T human cancer cell lines as well as similar or greater growth inhibitory activities than did combretastain A-4 against DLD-1, HR, MCF-7, DU145, HONE-1, and MES-SA/DX5 human cancer cell lines. Structure-activity relationship information revealed that introduction of an amino group at the ortho position of the benzophenone ring plays an integral role for increased growth inhibition.

Original languageEnglish
Pages (from-to)2556-2562
Number of pages7
JournalJournal of Medicinal Chemistry
Volume45
Issue number12
DOIs
Publication statusPublished - Jun 6 2002
Externally publishedYes

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Antimitotic Agents
Structure-Activity Relationship
Tubulin Modulators
Cells
Lead compounds
Derivatives
Cell Line
G2 Phase
Tubulin
Growth
Skeleton
Polymerization
Cell Division
Inhibitory Concentration 50
Neoplasms
In Vitro Techniques
combretastatin
benzophenone
fosbretabulin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents. / Liou, Jing Ping; Chang, Chun Wei; Song, Jeng Shin; Yang, Yung Ning; Yeh, Ching Fang; Tseng, Huan Yi; Lo, Yu Kang; Chang, Yi Ling; Chang, Chung Ming; Hsieh, Hsing Pang.

In: Journal of Medicinal Chemistry, Vol. 45, No. 12, 06.06.2002, p. 2556-2562.

Research output: Contribution to journalArticle

Liou, JP, Chang, CW, Song, JS, Yang, YN, Yeh, CF, Tseng, HY, Lo, YK, Chang, YL, Chang, CM & Hsieh, HP 2002, 'Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents', Journal of Medicinal Chemistry, vol. 45, no. 12, pp. 2556-2562. https://doi.org/10.1021/jm010365+
Liou, Jing Ping ; Chang, Chun Wei ; Song, Jeng Shin ; Yang, Yung Ning ; Yeh, Ching Fang ; Tseng, Huan Yi ; Lo, Yu Kang ; Chang, Yi Ling ; Chang, Chung Ming ; Hsieh, Hsing Pang. / Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents. In: Journal of Medicinal Chemistry. 2002 ; Vol. 45, No. 12. pp. 2556-2562.
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