- Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors
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A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity.
- Liu, Mingmei,Hou, Yunlei,Yin, Weile,Zhou, Shunguang,Qian, Ping,Guo, Zhuang,Xu, Liying,Zhao, Yangfang
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- Arylazide additions to α- and β- aminoacrylonitriles: Synthesis of 5-amino and 4-cyano-1,2,3-triazoles. Kinetic study of the cycloaddition
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Arylazides reacted with α-aminoacrylonitriles 1 (captodative olefins) to produce in excellant yields 5-amino-1-aryl-1,2,3-triazoles.HCN was spontaneously eliminated from the corresponding triazoline.Reaction of the same 1,3-dipoles with β-aminoacrylonitri
- Derdour, A.,Benabdallah, T.,Merah, B.,Texier, F.
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- ADDITION DIPOLAIRE-1,3 AUX OLEFINS POTANT UNE SUBSTITUTION CAPTODATIVE: REACTIVITE COMPAREE DES α ET DES β AMINO ACRYLONITRILES VIS A VIS DES ARYLAZIDES.
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Arylazides reacted with α amino-acrylonitriles 1 to produce 1-aryl-5-amono-triazoles, and with β amiono-acrylonitriles 2 to give 1-aryl-4-cyano-triazoles.Kinetics showed the Hammett ρ to be > ? and therefore, these reactions are controlled by LUMOazide-HOMOolefin interaction.Despite the captodative substitution in 1, the very small reactivity difference observed between the two isomers 1 and 2 (ΔΔE ca 500 cal.M-1) does'nt agree with a diradical intermediate.
- Texier, F.,Derdour, A.,Benhaoua, H.,Benabdellah, T.,Yebdri, O.
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p. 1893 - 1896
(2007/10/02)
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