168697-95-8Relevant academic research and scientific papers
Structure based design of a series of potent and selective non peptidic PTP-1B inhibitors
Lau, Cheuk K.,Bayly, Christopher I.,Gauthier, Jacques Yves,Li, Chun Sing,Therien, Michel,Asante-Appiah, Ernest,Cromlish, Wanda,Boie, Yves,Forghani, Farnaz,Desmarais, Sylvie,Wang, Qingping,Skorey, Kathryn,Waddleton, Deena,Payette, Paul,Ramachandran, Chidambaram,Kennedy, Brian P.,Scapin, Giovana
, p. 1043 - 1048 (2007/10/03)
A series of benzotriazole phenyldifluoromethylphosphonic acids were found to be potent PTP-1B inhibitors. Molecular modeling on the X-ray crystal structure of the lead structure led to the design of potent PTP-1B inhibitors that show moderate selectivity against TC-PTP, a very closely related protein tyrosine phosphatase.
1-(cyanomethyl)benzotriazole as a convenient precursor for the synthesis of 2-substituted thiazoles
Katritzky,Chen,Yang
, p. 5638 - 5642 (2007/10/03)
Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with α-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.
