192817-76-8Relevant academic research and scientific papers
Discovery of novel N-benzylbenzamide derivatives as tubulin polymerization inhibitors with potent antitumor activities
Zhu, Huajian,Li, Wenlong,Shuai, Wen,Liu, Yang,Yang, Limei,Tan, Yuchen,Zheng, Tiandong,Yao, Hong,Xu, Jinyi,Zhu, Zheying,Yang, Dong-Hua,Chen, Zhe-Sheng,Xu, Shengtao
, (2021/03/08)
A series of novel N-benzylbenzamide derivatives were designed and synthesized as tubulin polymerization inhibitors. Among fifty-one target compounds, compound 20b exhibited significant antiproliferative activities with IC50 values ranging from 12 to 27 nM against several cancer cell lines, and possessed good plasma stability and satisfactory physicochemical properties. Mechanism studies demonstrated that 20b bound to the colchicine binding site and displayed potent anti-vascular activity. Notably, the corresponding disodium phosphate 20b-P exhibited an excellent safety profile with the LD50 value of 599.7 mg/kg (i.v. injection), meanwhile, it significantly inhibited tumor growth and decreased microvessel density in liver cancer cell H22 allograft mouse model without obvious toxicity. Collectively, 20b and 20b-P are novel promising anti-tubulin agents with more druggable properties and deserve to be further investigated for cancer therapy.
Tandem Wolff rearrangement-'tert-amino effect' sequence: Synthesis of 2-oxoindolinium enolate derivatives
Leost, Francoise,Chantegrel, Bernard,Deshayes, Christian
, p. 7557 - 7576 (2007/10/03)
The thermolysis of 1-diazo-2-oxo-(2-N,N-disubstituted aminophenyl)ethylphosphonates 1 gave rise to 2-oxoindolinium enolate derivatives 4 through Wolff rearrangement and interaction of the tert-amino moiety with the ketene functionality. Variable amounts of either ammonium ylides 5 or of products resulting from their transformations were also formed during the course of the reaction. If the amino moiety was substituted by a benzyl or an allyl group, indolinones, resulting from [1,3] or [1,2] benzylic or allylic shifts, were isolated in place of compounds 4 and 5.
Tandem Wolff rearrangement-'tert-amino effect' sequence: Synthesis of 2-oxoindolinium enolate and 1H-2-benzopyrane derivatives
Chantegrel,Deshayes,Faure
, p. 7859 - 7862 (2007/10/02)
The thermal decomposition of dimethyl 1-diazo-2-oxo-(2-N,N-disubstituted aminophenyl)ethylphosphonates 1 gave rise to 2-oxoindolinium enolates 3 resulting from a Wolff rearrangement followed by attack of the nitrogen atom on the intermediate ketene moiety
