Concise syntheses of 7-anilino-indoline-N-benzenesulfonamides as antimitotic and vascular disrupting agents

Samir Mehndiratta; Yi-Fang Chiang; Mei-Jung Lai; Hsueh Yun Lee; Mei Chuan Chen; Ching-Chuan Kuo; Chi-Yen Chang; Jang-Yang Chang; Jing Ping Liou

doi:10.1016/j.bmc.2014.06.042

Concise syntheses of 7-anilino-indoline-N-benzenesulfonamides as antimitotic and vascular disrupting agents

Samir Mehndiratta, Yi-Fang Chiang, Mei-Jung Lai, Hsueh Yun Lee, Mei Chuan Chen, Ching-Chuan Kuo, Chi-Yen Chang, Jang-Yang Chang, Jing Ping Liou

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Described herein is the development of a novel series of 7-anilino-indoline-N-benzenesulfonamides, derived from ABT751 (1), as potent anticancer agents. Amongst the synthesized series, compounds 6, 12, 13, and 14 have shown comparable to better anticancer activity on comparing with compound 1. 7-(4-Cyanophenylamino)-1-(4-methoxybenzenesulfonyl)indoline (13) was found to be the most potent one with up to 6 fold better activity against KB, HT29, and MKN45 cancer cell lines with IC₅₀ values of 49.7, 149, and 92 nM, respectively. Compound 13 was also found inhibiting multidrug resistant cancer cell lines, blocking cell cycle at G2/M phase, and inhibiting tubulin polymerization. Capillary disruption assay results revealed that compound 13 was able to disrupt formed capillaries in a concentration-dependent manner without affecting cell viability.

Original language	English
Pages (from-to)	4917-4923
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	22
Issue number	17
DOIs	https://doi.org/10.1016/j.bmc.2014.06.042
Publication status	Published - Sept 1 2014

Keywords

ABT751
Antimitotic
CA-4
Vascular-disrupting agents

ASJC Scopus subject areas

Drug Discovery
Molecular Medicine
Molecular Biology
Biochemistry
Clinical Biochemistry
Pharmaceutical Science
Organic Chemistry

UN SDGs

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

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10.1016/j.bmc.2014.06.042

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title = "Concise syntheses of 7-anilino-indoline-N-benzenesulfonamides as antimitotic and vascular disrupting agents",

abstract = "Described herein is the development of a novel series of 7-anilino-indoline-N-benzenesulfonamides, derived from ABT751 (1), as potent anticancer agents. Amongst the synthesized series, compounds 6, 12, 13, and 14 have shown comparable to better anticancer activity on comparing with compound 1. 7-(4-Cyanophenylamino)-1-(4-methoxybenzenesulfonyl)indoline (13) was found to be the most potent one with up to 6 fold better activity against KB, HT29, and MKN45 cancer cell lines with IC50 values of 49.7, 149, and 92 nM, respectively. Compound 13 was also found inhibiting multidrug resistant cancer cell lines, blocking cell cycle at G2/M phase, and inhibiting tubulin polymerization. Capillary disruption assay results revealed that compound 13 was able to disrupt formed capillaries in a concentration-dependent manner without affecting cell viability.",

keywords = "ABT751, Antimitotic, CA-4, Vascular-disrupting agents",

author = "Samir Mehndiratta and Yi-Fang Chiang and Mei-Jung Lai and Lee, {Hsueh Yun} and Chen, {Mei Chuan} and Ching-Chuan Kuo and Chi-Yen Chang and Jang-Yang Chang and Liou, {Jing Ping}",

year = "2014",

month = sep,

day = "1",

doi = "10.1016/j.bmc.2014.06.042",

language = "English",

volume = "22",

pages = "4917--4923",

journal = "Bioorganic and Medicinal Chemistry",

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TY - JOUR

T1 - Concise syntheses of 7-anilino-indoline-N-benzenesulfonamides as antimitotic and vascular disrupting agents

AU - Mehndiratta, Samir

AU - Chiang, Yi-Fang

AU - Lai, Mei-Jung

AU - Lee, Hsueh Yun

AU - Chen, Mei Chuan

AU - Kuo, Ching-Chuan

AU - Chang, Chi-Yen

AU - Chang, Jang-Yang

AU - Liou, Jing Ping

PY - 2014/9/1

Y1 - 2014/9/1

N2 - Described herein is the development of a novel series of 7-anilino-indoline-N-benzenesulfonamides, derived from ABT751 (1), as potent anticancer agents. Amongst the synthesized series, compounds 6, 12, 13, and 14 have shown comparable to better anticancer activity on comparing with compound 1. 7-(4-Cyanophenylamino)-1-(4-methoxybenzenesulfonyl)indoline (13) was found to be the most potent one with up to 6 fold better activity against KB, HT29, and MKN45 cancer cell lines with IC50 values of 49.7, 149, and 92 nM, respectively. Compound 13 was also found inhibiting multidrug resistant cancer cell lines, blocking cell cycle at G2/M phase, and inhibiting tubulin polymerization. Capillary disruption assay results revealed that compound 13 was able to disrupt formed capillaries in a concentration-dependent manner without affecting cell viability.

AB - Described herein is the development of a novel series of 7-anilino-indoline-N-benzenesulfonamides, derived from ABT751 (1), as potent anticancer agents. Amongst the synthesized series, compounds 6, 12, 13, and 14 have shown comparable to better anticancer activity on comparing with compound 1. 7-(4-Cyanophenylamino)-1-(4-methoxybenzenesulfonyl)indoline (13) was found to be the most potent one with up to 6 fold better activity against KB, HT29, and MKN45 cancer cell lines with IC50 values of 49.7, 149, and 92 nM, respectively. Compound 13 was also found inhibiting multidrug resistant cancer cell lines, blocking cell cycle at G2/M phase, and inhibiting tubulin polymerization. Capillary disruption assay results revealed that compound 13 was able to disrupt formed capillaries in a concentration-dependent manner without affecting cell viability.

KW - ABT751

KW - Antimitotic

KW - CA-4

KW - Vascular-disrupting agents

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M3 - Article

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SN - 0968-0896

VL - 22

SP - 4917

EP - 4923

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 17

ER -

Concise syntheses of 7-anilino-indoline-N-benzenesulfonamides as antimitotic and vascular disrupting agents

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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