2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents

Jang Yang Chang, Ming Fang Yang, Chi Yen Chang, Chi Ming Chen, Ching Chuan Kuo, Jing Ping Liou

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with IC50 values of 1.6, 1.7, and 1.8 μM, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine and approximately as active as combretastatin A-4. They also displayed antiproliferative activity with an IC50 values ranging from 11 to 44 nM in a variety of human cell lines from different organs. Structure activity relationship information suggests that the NH2 substituent at the 2-position of either ring A or ring B in combretastatin molecular skeleton may play an important role in the bioactivity of this series of compounds.

Original languageEnglish
Pages (from-to)6412-6415
Number of pages4
JournalJournal of Medicinal Chemistry
Volume49
Issue number21
DOIs
Publication statusPublished - Oct 2006

Fingerprint

Tubulin Modulators
Antimitotic Agents
Colchicine
Tubulin
Bioactivity
Inhibitory Concentration 50
Polymerization
Cells
Derivatives
Structure-Activity Relationship
Skeleton
Cell Line
combretastatin
fosbretabulin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents. / Chang, Jang Yang; Yang, Ming Fang; Chang, Chi Yen; Chen, Chi Ming; Kuo, Ching Chuan; Liou, Jing Ping.

In: Journal of Medicinal Chemistry, Vol. 49, No. 21, 10.2006, p. 6412-6415.

Research output: Contribution to journalArticle

Chang, Jang Yang ; Yang, Ming Fang ; Chang, Chi Yen ; Chen, Chi Ming ; Kuo, Ching Chuan ; Liou, Jing Ping. / 2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents. In: Journal of Medicinal Chemistry. 2006 ; Vol. 49, No. 21. pp. 6412-6415.
@article{7e912b815e8941d1bb46f27461df8bb5,
title = "2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents",
abstract = "A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with IC50 values of 1.6, 1.7, and 1.8 μM, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine and approximately as active as combretastatin A-4. They also displayed antiproliferative activity with an IC50 values ranging from 11 to 44 nM in a variety of human cell lines from different organs. Structure activity relationship information suggests that the NH2 substituent at the 2-position of either ring A or ring B in combretastatin molecular skeleton may play an important role in the bioactivity of this series of compounds.",
author = "Chang, {Jang Yang} and Yang, {Ming Fang} and Chang, {Chi Yen} and Chen, {Chi Ming} and Kuo, {Ching Chuan} and Liou, {Jing Ping}",
year = "2006",
month = "10",
doi = "10.1021/jm060616k",
language = "English",
volume = "49",
pages = "6412--6415",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - 2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents

AU - Chang, Jang Yang

AU - Yang, Ming Fang

AU - Chang, Chi Yen

AU - Chen, Chi Ming

AU - Kuo, Ching Chuan

AU - Liou, Jing Ping

PY - 2006/10

Y1 - 2006/10

N2 - A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with IC50 values of 1.6, 1.7, and 1.8 μM, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine and approximately as active as combretastatin A-4. They also displayed antiproliferative activity with an IC50 values ranging from 11 to 44 nM in a variety of human cell lines from different organs. Structure activity relationship information suggests that the NH2 substituent at the 2-position of either ring A or ring B in combretastatin molecular skeleton may play an important role in the bioactivity of this series of compounds.

AB - A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with IC50 values of 1.6, 1.7, and 1.8 μM, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine and approximately as active as combretastatin A-4. They also displayed antiproliferative activity with an IC50 values ranging from 11 to 44 nM in a variety of human cell lines from different organs. Structure activity relationship information suggests that the NH2 substituent at the 2-position of either ring A or ring B in combretastatin molecular skeleton may play an important role in the bioactivity of this series of compounds.

UR - http://www.scopus.com/inward/record.url?scp=33750134570&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33750134570&partnerID=8YFLogxK

U2 - 10.1021/jm060616k

DO - 10.1021/jm060616k

M3 - Article

C2 - 17034147

AN - SCOPUS:33750134570

VL - 49

SP - 6412

EP - 6415

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 21

ER -