Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction

Gui Ting Song; Nicholas McConnell; Zhong Zhu Chen; Xiao Fang Yao; Jiu Hong Huang; Jie Lei; Hui Kuan Lin; Brendan Frett; Hong yu Li; Zhi Gang Xu

doi:10.1002/adsc.201800728

Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction

Gui Ting Song, Nicholas McConnell, Zhong Zhu Chen, Xiao Fang Yao, Jiu Hong Huang, Jie Lei, Hui Kuan Lin, Brendan Frett, Hong yu Li, Zhi Gang Xu

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

10 Scopus citations

Abstract

A transition-metal free, high yielding and efficient three-component reaction was designed and incorporated into two sequential oxidation and cyclization reaction cascades in one-pot with the assistance of microwave irradiation. A chemical collection of functionalized 3-substituted imidazopyridines was prepared by means of the mild reaction and simple operational procedure. The reaction has a broad tolerance for a variety of substituted carbonyl aldehydes, anilines and 2-phenyl-imidazo[1,2-a]pyridines. Screening in several cancer cell lines was conducted. Compound 9 i exhibited good potency against HeLa cell lines and this work validated the feasibility of the methodology for generating bioactive compounds. (Figure presented.).

Original language	English (US)
Pages (from-to)	3655-3661
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	19
DOIs	https://doi.org/10.1002/adsc.201800728
State	Published - Oct 4 2018
Externally published	Yes

Keywords

Anti-cancer
Imidazopyridines
multicomponent reactions (MCRs)
One-pot
three-component reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201800728

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Song, G. T., McConnell, N., Chen, Z. Z., Yao, X. F., Huang, J. H., Lei, J., Lin, H. K., Frett, B., Li, H. Y., & Xu, Z. G. (2018). Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction. Advanced Synthesis and Catalysis, 360(19), 3655-3661. https://doi.org/10.1002/adsc.201800728

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title = "Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction",

abstract = "A transition-metal free, high yielding and efficient three-component reaction was designed and incorporated into two sequential oxidation and cyclization reaction cascades in one-pot with the assistance of microwave irradiation. A chemical collection of functionalized 3-substituted imidazopyridines was prepared by means of the mild reaction and simple operational procedure. The reaction has a broad tolerance for a variety of substituted carbonyl aldehydes, anilines and 2-phenyl-imidazo[1,2-a]pyridines. Screening in several cancer cell lines was conducted. Compound 9 i exhibited good potency against HeLa cell lines and this work validated the feasibility of the methodology for generating bioactive compounds. (Figure presented.).",

keywords = "Anti-cancer, Imidazopyridines, multicomponent reactions (MCRs), One-pot, three-component reaction",

author = "Song, {Gui Ting} and Nicholas McConnell and Chen, {Zhong Zhu} and Yao, {Xiao Fang} and Huang, {Jiu Hong} and Jie Lei and Lin, {Hui Kuan} and Brendan Frett and Li, {Hong yu} and Xu, {Zhi Gang}",

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year = "2018",

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doi = "10.1002/adsc.201800728",

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AU - Song, Gui Ting

AU - McConnell, Nicholas

AU - Chen, Zhong Zhu

AU - Yao, Xiao Fang

AU - Huang, Jiu Hong

AU - Lei, Jie

AU - Lin, Hui Kuan

AU - Frett, Brendan

AU - Li, Hong yu

AU - Xu, Zhi Gang

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AB - A transition-metal free, high yielding and efficient three-component reaction was designed and incorporated into two sequential oxidation and cyclization reaction cascades in one-pot with the assistance of microwave irradiation. A chemical collection of functionalized 3-substituted imidazopyridines was prepared by means of the mild reaction and simple operational procedure. The reaction has a broad tolerance for a variety of substituted carbonyl aldehydes, anilines and 2-phenyl-imidazo[1,2-a]pyridines. Screening in several cancer cell lines was conducted. Compound 9 i exhibited good potency against HeLa cell lines and this work validated the feasibility of the methodology for generating bioactive compounds. (Figure presented.).

KW - Anti-cancer

KW - Imidazopyridines

KW - multicomponent reactions (MCRs)

KW - One-pot

KW - three-component reaction

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DO - 10.1002/adsc.201800728

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ER -

Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction

Abstract

Keywords

ASJC Scopus subject areas

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