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

30 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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10.1021/acs.joc.9b01385

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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,

day = "4",

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

language = "English (US)",

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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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