Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists

Chia Liang Tai; Ming Shiu Hung; Vijay D. Pawar; Shi Liang Tseng; Jen Shin Song; Wan Ping Hsieh; Hua Hao Chiu; Hui Chuan Wu; Min Tsang Hsieh; Chun Wei Kuo; Chia Chien Hsieh; Jing Po Tsao; Yu Sheng Chao; Kak Shan Shia

doi:10.1039/b716434c

Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists

Chia Liang Tai, Ming Shiu Hung, Vijay D. Pawar, Shi Liang Tseng, Jen Shin Song, Wan Ping Hsieh, Hua Hao Chiu, Hui Chuan Wu, Min Tsang Hsieh, Chun Wei Kuo, Chia Chien Hsieh, Jing Po Tsao, Yu Sheng Chao, Kak Shan Shia^*

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

A novel class of (5-(pent-1-enyl)thiophen-2-yl)pyrazole antagonists was discovered, many of which exhibited potent CB1 activity and good CB1/2 selectivity, suggesting that along with a 1,3-transposition of the carbonyl of the pyrazole 3-carboxamide, bioisosteric replacement of the conventional pyrazole 5-aryl group with a thienyl ring substituted with an appropriate alkenyl moiety is viable.

Original language	English
Pages (from-to)	447-450
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	6
Issue number	3
DOIs	https://doi.org/10.1039/b716434c
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Tai, C. L., Hung, M. S., Pawar, V. D., Tseng, S. L., Song, J. S., Hsieh, W. P., Chiu, H. H., Wu, H. C., Hsieh, M. T., Kuo, C. W., Hsieh, C. C., Tsao, J. P., Chao, Y. S., & Shia, K. S. (2008). Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists. Organic and Biomolecular Chemistry, 6(3), 447-450. https://doi.org/10.1039/b716434c

Tai, CL, Hung, MS, Pawar, VD, Tseng, SL, Song, JS, Hsieh, WP, Chiu, HH, Wu, HC, Hsieh, MT, Kuo, CW, Hsieh, CC, Tsao, JP, Chao, YS & Shia, KS 2008, 'Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists', Organic and Biomolecular Chemistry, vol. 6, no. 3, pp. 447-450. https://doi.org/10.1039/b716434c

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title = "Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists",

abstract = "A novel class of (5-(pent-1-enyl)thiophen-2-yl)pyrazole antagonists was discovered, many of which exhibited potent CB1 activity and good CB1/2 selectivity, suggesting that along with a 1,3-transposition of the carbonyl of the pyrazole 3-carboxamide, bioisosteric replacement of the conventional pyrazole 5-aryl group with a thienyl ring substituted with an appropriate alkenyl moiety is viable.",

author = "Tai, {Chia Liang} and Hung, {Ming Shiu} and Pawar, {Vijay D.} and Tseng, {Shi Liang} and Song, {Jen Shin} and Hsieh, {Wan Ping} and Chiu, {Hua Hao} and Wu, {Hui Chuan} and Hsieh, {Min Tsang} and Kuo, {Chun Wei} and Hsieh, {Chia Chien} and Tsao, {Jing Po} and Chao, {Yu Sheng} and Shia, {Kak Shan}",

year = "2008",

doi = "10.1039/b716434c",

language = "English",

volume = "6",

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AU - Tai, Chia Liang

AU - Hung, Ming Shiu

AU - Pawar, Vijay D.

AU - Tseng, Shi Liang

AU - Song, Jen Shin

AU - Hsieh, Wan Ping

AU - Chiu, Hua Hao

AU - Wu, Hui Chuan

AU - Hsieh, Min Tsang

AU - Kuo, Chun Wei

AU - Hsieh, Chia Chien

AU - Tsao, Jing Po

AU - Chao, Yu Sheng

AU - Shia, Kak Shan

PY - 2008

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AB - A novel class of (5-(pent-1-enyl)thiophen-2-yl)pyrazole antagonists was discovered, many of which exhibited potent CB1 activity and good CB1/2 selectivity, suggesting that along with a 1,3-transposition of the carbonyl of the pyrazole 3-carboxamide, bioisosteric replacement of the conventional pyrazole 5-aryl group with a thienyl ring substituted with an appropriate alkenyl moiety is viable.

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Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists

Abstract

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