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

doi:10.1021/jm010365+

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 journal › Article › peer-review

134 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 language	English
Pages (from-to)	2556-2562
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	45
Issue number	12
DOIs	https://doi.org/10.1021/jm010365+
Publication status	Published - Jun 6 2002
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jm010365+

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@article{2d788668db2c4abb9cddc8e399c566a0,

title = "Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents",

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.",

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

year = "2002",

month = jun,

day = "6",

doi = "10.1021/jm010365+",

language = "English",

volume = "45",

pages = "2556--2562",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

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T1 - Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents

AU - Liou, Jing Ping

AU - Chang, Chun Wei

AU - Song, Jeng Shin

AU - Yang, Yung Ning

AU - Yeh, Ching Fang

AU - Tseng, Huan Yi

AU - Lo, Yu Kang

AU - Chang, Yi Ling

AU - Chang, Chung Ming

AU - Hsieh, Hsing Pang

PY - 2002/6/6

Y1 - 2002/6/6

N2 - 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.

AB - 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.

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 12

ER -

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

Abstract

ASJC Scopus subject areas

UN SDGs

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