Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

Chien Ting Chen; Mei Hua Hsu; Yung Yi Cheng; Chin Yu Liu; Li Chen Chou; Li Jiau Huang; Tian Shung Wu; Xiaoming Yang; Kuo Hsiung Lee; Sheng Chu Kuo

doi:10.1016/j.ejmech.2011.10.017

Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

Chien Ting Chen
, Mei Hua Hsu
, Yung Yi Cheng
, Chin Yu Liu
, Li Chen Chou
, Li Jiau Huang
, Tian Shung Wu
, Xiaoming Yang
, Kuo Hsiung Lee
, Sheng Chu Kuo

School of Pharmacy

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

36 Citations (Scopus)

Abstract

6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure-activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization.

Original language	English
Pages (from-to)	6046-6056
Number of pages	11
Journal	European Journal of Medicinal Chemistry
Volume	46
Issue number	12
DOIs	https://doi.org/10.1016/j.ejmech.2011.10.017
Publication status	Published - 2011 Dec

UN SDGs

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

SDG 3 Good Health and Well-being

All Science Journal Classification (ASJC) codes

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2011.10.017

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Chen, C. T., Hsu, M. H., Cheng, Y. Y., Liu, C. Y., Chou, L. C., Huang, L. J., Wu, T. S., Yang, X., Lee, K. H., & Kuo, S. C. (2011). Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs. European Journal of Medicinal Chemistry, 46(12), 6046-6056. https://doi.org/10.1016/j.ejmech.2011.10.017

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title = "Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs",

abstract = "6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure-activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization.",

author = "Chen, \{Chien Ting\} and Hsu, \{Mei Hua\} and Cheng, \{Yung Yi\} and Liu, \{Chin Yu\} and Chou, \{Li Chen\} and Huang, \{Li Jiau\} and Wu, \{Tian Shung\} and Xiaoming Yang and Lee, \{Kuo Hsiung\} and Kuo, \{Sheng Chu\}",

note = "Funding Information: The investigation was supported by research grants from the National Science Council of the Republic of China awarded to S. C. Kuo ( NSC 97-2323-B-039-001 ; NSC 98-2323-B-039-001 ). Experiments and data analysis were performed in part through the use of the Medical Research Core Facilities Center, Office of Research \& Development, China Medical University, Taichung, Taiwan, R.O.C. ",

year = "2011",

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doi = "10.1016/j.ejmech.2011.10.017",

language = "English",

volume = "46",

pages = "6046--6056",

journal = "European Journal of Medicinal Chemistry",

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T1 - Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

AU - Chen, Chien Ting

AU - Hsu, Mei Hua

AU - Cheng, Yung Yi

AU - Liu, Chin Yu

AU - Chou, Li Chen

AU - Huang, Li Jiau

AU - Wu, Tian Shung

AU - Yang, Xiaoming

AU - Lee, Kuo Hsiung

AU - Kuo, Sheng Chu

N1 - Funding Information: The investigation was supported by research grants from the National Science Council of the Republic of China awarded to S. C. Kuo ( NSC 97-2323-B-039-001 ; NSC 98-2323-B-039-001 ). Experiments and data analysis were performed in part through the use of the Medical Research Core Facilities Center, Office of Research & Development, China Medical University, Taichung, Taiwan, R.O.C.

PY - 2011/12

Y1 - 2011/12

N2 - 6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure-activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization.

AB - 6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure-activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization.

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Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

Abstract

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