Design, synthesis and biological evaluation of novel N-[4-(2-fluorophenoxy)pyridin-2-yl]cyclopropanecarboxamide derivatives as potential c-Met kinase inhibitors

Liu, Ju; Gong, Yifu; Shi, Jiantao; Hao, Xuechen; Wang, Yang; Zhou, Yunpeng; Hou, Yunlei; Liu, Yajing; Ding, Shuai; Chen, Ye

doi:10.1016/j.ejmech.2020.112244

Cited by 32 publications

(8 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N -Alkoxycarbonyl amides ( N -acyl carbamates) are important building blocks widely utilized in the synthesis of bioactive compounds . They have also found broad applications as a reacting motif for various organic transformations, for example, numerous C–N bond activation reactions have been developed based on the electronic manipulation of amide functionality with an N -alkoxycarbonyl group .…”

Section: Introductionmentioning

confidence: 99%

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Jeon

Lee

Chang

2021

Org. Process Res. Dev.

View full text Add to dashboard Cite

Herein, we describe the scalability and sustainability investigations toward the visible light-mediated amidation of aldehydes with N-chloro-N-sodio-carbamates. The practicality credentials of N-chloro-N-sodio-carbamates for their use in multigram scale amidation reactions are proven by scale-up productions and thermogravimetric analysis. The described amidation, which was previously hampered in sustainability perspectives by the use of α,α,α-trifluorotoluene solvent, is now improved through re-optimizations using ethyl acetate as an alternative green solvent. The generality of multigram scale amidations is demonstrated by the conversion of a selected list of aldehydes, in which the corresponding amides can be isolated in high purity without the need for special purification procedures.

show abstract

Section: Introductionmentioning

confidence: 99%

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Jeon

Lee

Chang

2021

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…Tyrosine-protein kinase Met is a structurally distinct member of a heterodimeric transmembrane receptor tyrosine kinase family, which has an extracellular α chain and a membrane spanning β chain. 20 Overexpression or abnormal activation of c-Met kinase has been reported to be associated with the formation and development of multiple cancers in liver, lung, prostate, breast, lymph, gastric and renal cancers. 21 Therefore, c-Met kinase has emerged as an attractive target for the development of antitumour agents.…”

Section: Discussionmentioning

confidence: 99%

A novel anti-lung cancer agent inhibits proliferation and epithelial–mesenchymal transition

Zhao

Guo

et al. 2022

J Int Med Res

View full text Add to dashboard Cite

Objective To synthesize a novel chalcone-1,3,4-thiadiazole hybrid and investigate its anticancer effects against NCI-H460 cells. Methods ( E)-3-(4-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one, 1,3-dibromopropane and 1,3,4-thiadiazole-2-thiol were used as chemical materials to synthesize compound ZW97. The NCI-H460 lung cancer cell line was selected to explore the antitumor effects of compound ZW97 in vitro and in vivo. Results Compound ZW97 selectively inhibited cell proliferation against lung cancer cell lines NCI-H460, HCC-44 and NCI-H3122 with IC50 values of 0.15 μM, 2.06 μM and 1.17 μM, respectively. ZW97 suppressed migration and the epithelial–mesenchymal transition process in NCI-H460 cells in a concentration-dependent manner. Based on the kinase activity results and docking analysis, compound ZW97 is a novel tyrosine-protein kinase Met (c-Met kinase) inhibitor. It also inhibited NCI-H460 cell growth in xenograft models without obvious toxicity to normal tissues. Conclusions Compound ZW97 is a potential c-Met inhibitor that might be a promising agent to treat lung cancer by inhibiting the epithelial–mesenchymal transition process.

show abstract

“…The AO penetrates the intact cell membrane and inserts nuclear DNA into the cell, causing emission of a bright green fluorescence. The EB can only penetrate cells with damaged membranes, embed nuclear DNA in agar, and emit orange fluorescence (18)(19)(20). Among them, normal cells appeared green.…”

Section: Apoptosis Of Fibroblasts After E2 Stimulationmentioning

confidence: 99%

Therapeutic Effects of 17β-Estradiol on Pelvic Organ Prolapse by Inhibiting Mfn2 Expression: An In Vitro Study

Wang

Xiao

et al. 2020

Front. Endocrinol.

View full text Add to dashboard Cite

ObjectiveTo assess the effects of 17β-estradiol (E2) on proliferation, apoptosis, and protein expressions of fibroblasts at different concentrations and time intervals to reveal the mechanism of E2 in the treatment of pelvic organ prolapse (POP).Study DesignThe uterosacral ligament fibroblasts were collected from seven POP patients for primary culture of fibroblasts. The culture media containing 0, 10-6, 10-7, 10-8, and 10-9 mol/L E2 were used for 24, 48, 72, and 96 h.Main Outcome MeasuresThe cells were collected for cell counting kit-8 (CCK-8), apoptosis, quantitative reverse transcription polymerase chain reaction (qRT-PCR), and Western blotting assays.ResultsCompared with the control group, in the values of fibroblasts cultured in 10-8 mol/L E2 for 72 h, the proliferation, mRNA and protein expression of Mitofusin-2 (Mfn2) separately increased (P < 0.05), decreased (P<0.001) and decreased (P<0.001). However, the expression level of procollagen 1A1/1A2/3A1 and cyclinD1 markedly increased (P<0.001, all), which was consistent with the results of protein level. What’s more, the expression of estrogen receptor α(ERα), estrogen receptor β(ERβ) and G protein-coupled receptor 30(GPR30) were significantly increased in 10-8 mol/L E2 group.ConclusionsE2 can inhibit the progress of POP by inhibiting the expression level of Mfn2, as well as promoting expression of procollagens and proliferation of fibroblasts. This effect is time- and concentration-dependent. Only when the estrogen concentration reaches 10-8 mol/L, the therapeutic effect is the greatest after 72 h.

show abstract

Design, synthesis and biological evaluation of novel N-[4-(2-fluorophenoxy)pyridin-2-yl]cyclopropanecarboxamide derivatives as potential c-Met kinase inhibitors

Cited by 32 publications

References 28 publications

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

A novel anti-lung cancer agent inhibits proliferation and epithelial–mesenchymal transition

Therapeutic Effects of 17β-Estradiol on Pelvic Organ Prolapse by Inhibiting Mfn2 Expression: An In Vitro Study

Contact Info

Product

Resources

About