A Carbonylation Approach Toward Activation of Csp2-H and Csp3-H Bonds: Cu-Catalyzed Regioselective Cross Coupling of Imidazo[1,2-a]pyridines with Methyl Hetarenes

Lei, Sai; Mai, Yingying; Yan, Caijuan; Mao, Jianwen; Cao, Hua

doi:10.1021/acs.orglett.6b01588

Cited by 87 publications

(21 citation statements)

References 67 publications

(14 reference statements)

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“…Imidazopyridines, one type of nitrogenous heterocycles, are largely used in medicinal application as they possess a wide spectrum of biological activities [1][2][3]. Imidazopyridines were reported to have anticancer properties in human cancer cell lines U251 (glioma), PC-3 (prostate), K-562 (leukemia), HCT-15 (colon), MCF7 (breast), SK-LU-1 (lung) [4], and LN-405 (glioblastoma) [5].…”

Section: Introductionmentioning

confidence: 99%

A Novel Imidazopyridine Derivative Exerts Anticancer Activity by Inducing Mitochondrial Pathway-Mediated Apoptosis

Wang

Song

et al. 2020

BioMed Research International

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Background. Cancer remains a major clinical challenge because of the lack of effective drug for its treatment. To find out novel cancer chemotherapeutic molecules, we explored the anticancer effect of novel imidazopyridine compound 9i and also investigated the underlying molecular mechanism. Methods. Human cervical cancer cell (HeLa) viability was measured by an MTT assay after treatment with compound 9i. Clonogenicity of HeLa cells was investigated by an in vitro colony formation assay. Cell death was visualized by propidium iodide (PI) staining. Fluorescence-activated cell sorting (FACS) was used to determine apoptosis and mitochondrial membrane potential in HeLa cells. The expression level of apoptosis-related proteins was also determined by western blot. Results. Compound 9i suppressed HeLa cell viability in a time- and dose-dependent manner. Compound 9i induced mitochondrial outer membrane permeabilization (MOMP), activated caspase cascade, and finally resulted in apoptosis. Conclusion. Compound 9i induces mitochondrial pathway-mediated apoptosis in human cervical cancer cells, suggesting that 9i could be a potential lead compound to be developed as a cancer therapeutic molecule.

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Section: Introductionmentioning

confidence: 99%

A Novel Imidazopyridine Derivative Exerts Anticancer Activity by Inducing Mitochondrial Pathway-Mediated Apoptosis

Wang

Song

et al. 2020

BioMed Research International

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“…In continuation of the work towards C(sp 2 )–H bond activation of IPs Lei et al have reported a novel copper-catalyzed cross coupling of 180 with methylheteroarenes 418 [196]. This reaction involved regioselective C-3 carbonylation of IP.…”

Section: Reviewmentioning

confidence: 99%

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Reen

Kumar

Sharma

2019

Beilstein J. Org. Chem.

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A comprehensive account of recent advances in the synthesis of imidazopyridines, assisted through transition-metal-catalyzed multicomponent reactions, C–H activation/functionalization and coupling reactions are highlighted in this review article. The basic illustration of this review comprises of schemes with concise account of explanatory text. The schemes depict the reaction conditions along with a quick look into the mechanism involved to render a deep understanding of the catalytic role. At some instances optimizations of certain features have been illustrated through tables, i.e., selectivity of catalyst, loading of the catalyst and percentage yield with different substrates. Each of the reported examples has been rigorously analyzed for reacting substrates, reaction conditions and transition metals used as the catalyst. This review will be helpful to the chemists in understanding the challenges associated with the reported methods as well as the future possibilities, both in the choice of substrates and catalysts. This review would be quite appealing to a wider range of organic chemists in academia and industrial R&D sectors working in the field of heterocyclic syntheses. In a nutshell, this review will be a guiding torch to envisage: (i) the role of various transition metals in the domain dedicated towards method development and (ii) for the modifications needed thereof in the R&D sector.

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“…Based on our previous work, we found that the copper/oxygen catalytic system is powerful and versatile in this field, which enables CDC to efficiently construct C−C and C−heteroatom bonds under facile conditions. Therefore, we continued our research on Csp 2 −H carbonylation of imidazo[1,2‐ a ]pyridine via Csp 3 −H oxidation of α ‐picoline derivatives under copper/oxygen catalytic system (Scheme ) . This transformation opened a new routes to synthesize C‐3 carbonyl imidazo[1,2‐ a ]pyridine derivatives, which involved at least two kinds of nitrogen heterocyclic framework.…”

Section: Synthesis Of Imidazo[12‐a]pyridine Via C−h Bond Functionalimentioning

confidence: 99%

Strategies for Synthesis of Imidazo[1,2‐a]pyridine Derivatives: Carbene Transformations or C−H Functionalizations

Cao

2018

The Chemical Record

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The imidazo [1,2-a]pyridines are an important target in organic synthetic chemistry and have attracted critical attention of chemists mainly due to the discovery of the interesting properties exhibited by a great number of imidazo[1,2-a]pyridine derivatives. Although lots of synthetic methods of imidazo[1,2-a]pyridines have been developed in the past years, the chemistry community faces continuing challenges to use green reagents, maximize atom economy and enrich the functional group diversity of product. Undoubtedly, with its low cost and lack of environmentally hazardous byproducts, cascade reactions and CÀH functionalizations are ideal strategies for this field. In this record we highlight some of our progress toward the goal to synthesis of imidazo[1,2-a]pyridine derivatives through carbene transformations or CÀH functionalizations.

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A Carbonylation Approach Toward Activation of C_sp2-H and C_sp3-H Bonds: Cu-Catalyzed Regioselective Cross Coupling of Imidazo[1,2-a]pyridines with Methyl Hetarenes

Cited by 87 publications

References 67 publications

A Novel Imidazopyridine Derivative Exerts Anticancer Activity by Inducing Mitochondrial Pathway-Mediated Apoptosis

A Novel Imidazopyridine Derivative Exerts Anticancer Activity by Inducing Mitochondrial Pathway-Mediated Apoptosis

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Strategies for Synthesis of Imidazo[1,2‐a]pyridine Derivatives: Carbene Transformations or C−H Functionalizations

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