180987-80-8Relevant articles and documents
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Novel carvedilol analogues that suppress store-overload-induced Ca 2+ release
Smith, Chris D.,Wang, Aixia,Vembaiyan, Kannan,Zhang, Jingqun,Xie, Cuihong,Zhou, Qiang,Wu, Guogen,Chen, S. R. Wayne,Back, Thomas G.
, p. 8626 - 8655 (2013/12/04)
Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the β-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.
Lewis acid mediated nucleophilic ring-opening of 1-Benzhydryl Azetidine-3-ol with aryl alcohols: A formal synthesis of carvedilol
Krishna Reddy,Ramamohan,Ganesh,Srinivas,Mukkanti,Madhusudhan
, p. 3468 - 3472 (2012/07/30)
Lewis acid mediated nucleophilic azetidine ring opening of 1-benzhydrylazetidine-3-ol with phenolic oxygen as nucleophile is reported. This approach was also utilized successfully to synthesize, carvedilol a β-adrenergic blocking agent.
