Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot

Yong Li; Jiu Hong Huang; Juan Li Wang; Gui Ting Song; Dian Yong Tang; Fang Yao; Hui Kuan Lin; Wei Yan; Hong Yu Li; Zhi Gang Xu; Zhong Zhu Chen

doi:10.1021/acs.joc.9b01385

Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot

Yong Li, Jiu Hong Huang, Juan Li Wang, Gui Ting Song, Dian Yong Tang, Fang Yao, Hui Kuan Lin, Wei Yan, Hong Yu Li, Zhi Gang Xu, Zhong Zhu Chen

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

26 Scopus citations

Abstract

A facile and metal-free one-pot protocol for the synthesis of fused imidazopyridine scaffolds has been developed. This novel protocol combines the Groebke-Blackburn-Bienaymé reaction (GBBR) with a sequential TBAB-mediated cyclization cascade. Biological evaluation demonstrated that compound 6a inhibits human prostate cancer cell DU-145 proliferation with an IC₅₀ of 1.6 μM. The molecular mechanism study indicates that 6a significantly suppresses the oncogenic Erk kinase phosphorylation at 3 μM.

Original language	English (US)
Pages (from-to)	12632-12638
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	84
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.9b01385
State	Published - Oct 4 2019
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Li, Y., Huang, J. H., Wang, J. L., Song, G. T., Tang, D. Y., Yao, F., Lin, H. K., Yan, W., Li, H. Y., Xu, Z. G., & Chen, Z. Z. (2019). Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot. Journal of Organic Chemistry, 84(19), 12632-12638. https://doi.org/10.1021/acs.joc.9b01385

Li, Y, Huang, JH, Wang, JL, Song, GT, Tang, DY, Yao, F, Lin, HK, Yan, W , Li, HY, Xu, ZG & Chen, ZZ 2019, 'Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot', Journal of Organic Chemistry, vol. 84, no. 19, pp. 12632-12638. https://doi.org/10.1021/acs.joc.9b01385

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title = "Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaym{\'e} and TBAB-Mediated Cascade Reaction in One Pot",

abstract = "A facile and metal-free one-pot protocol for the synthesis of fused imidazopyridine scaffolds has been developed. This novel protocol combines the Groebke-Blackburn-Bienaym{\'e} reaction (GBBR) with a sequential TBAB-mediated cyclization cascade. Biological evaluation demonstrated that compound 6a inhibits human prostate cancer cell DU-145 proliferation with an IC50 of 1.6 μM. The molecular mechanism study indicates that 6a significantly suppresses the oncogenic Erk kinase phosphorylation at 3 μM.",

author = "Yong Li and Huang, {Jiu Hong} and Wang, {Juan Li} and Song, {Gui Ting} and Tang, {Dian Yong} and Fang Yao and Lin, {Hui Kuan} and Wei Yan and Li, {Hong Yu} and Xu, {Zhi Gang} and Chen, {Zhong Zhu}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

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doi = "10.1021/acs.joc.9b01385",

language = "English (US)",

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T1 - Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot

AU - Li, Yong

AU - Huang, Jiu Hong

AU - Wang, Juan Li

AU - Song, Gui Ting

AU - Tang, Dian Yong

AU - Yao, Fang

AU - Lin, Hui Kuan

AU - Yan, Wei

AU - Li, Hong Yu

AU - Xu, Zhi Gang

AU - Chen, Zhong Zhu

PY - 2019/10/4

Y1 - 2019/10/4

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AB - A facile and metal-free one-pot protocol for the synthesis of fused imidazopyridine scaffolds has been developed. This novel protocol combines the Groebke-Blackburn-Bienaymé reaction (GBBR) with a sequential TBAB-mediated cyclization cascade. Biological evaluation demonstrated that compound 6a inhibits human prostate cancer cell DU-145 proliferation with an IC50 of 1.6 μM. The molecular mechanism study indicates that 6a significantly suppresses the oncogenic Erk kinase phosphorylation at 3 μM.

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Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot

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