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

Pharmacology and Toxicology

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

8 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

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201800728

Cite this

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

@article{3fdf4f5d1e1e4ecdba2a10227827f460,

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, One-pot, multicomponent reactions (MCRs), 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}",

note = "Funding Information: The authors would like to thank Chongqing Science and Technology Committee Project of China under grant No. cstc2016jcyjA0534 and cstc2015zdcy-ztzx120003; The grants from Chongqing Education commission Project of China under Grant No. KJZH17129, KJ1501130, KJ1711284 and KJ1711287; Chongqing University of Arts and Science R2015BX03. HL and BF were supported by the grants (NIH 1R01CA194094-010 and 1R01CA197178-01A1). HKL was supported by the grants (NIH R01 CA182424 and R01CA193813). This work was also supported by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences from the National Institutes of Health under grant number “P20 GM109005”. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = oct,

day = "4",

doi = "10.1002/adsc.201800728",

language = "English (US)",

volume = "360",

pages = "3655--3661",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "19",

}

TY - JOUR

T1 - Diversity-Oriented Synthesis of Functionalized Imidazopyridine Analogues with Anti-Cancer Activity through a Transition-Metal Free, One-pot Cascade Reaction

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

N1 - Funding Information: The authors would like to thank Chongqing Science and Technology Committee Project of China under grant No. cstc2016jcyjA0534 and cstc2015zdcy-ztzx120003; The grants from Chongqing Education commission Project of China under Grant No. KJZH17129, KJ1501130, KJ1711284 and KJ1711287; Chongqing University of Arts and Science R2015BX03. HL and BF were supported by the grants (NIH 1R01CA194094-010 and 1R01CA197178-01A1). HKL was supported by the grants (NIH R01 CA182424 and R01CA193813). This work was also supported by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences from the National Institutes of Health under grant number “P20 GM109005”. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/10/4

Y1 - 2018/10/4

N2 - 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.).

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 - One-pot

KW - multicomponent reactions (MCRs)

KW - three-component reaction

UR - http://www.scopus.com/inward/record.url?scp=85053061778&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85053061778&partnerID=8YFLogxK

U2 - 10.1002/adsc.201800728

DO - 10.1002/adsc.201800728

M3 - Article

AN - SCOPUS:85053061778

VL - 360

SP - 3655

EP - 3661

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 19

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

Access to Document

Other files and links

Fingerprint

CCDC 1815595: Experimental Crystal Structure Determination

Cite this

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

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1815595: Experimental Crystal Structure Determination

Cite this