652968-46-2Relevant articles and documents
Palladium(II)-η3-Allyl Complexes Bearing N-Trifluoromethyl N-Heterocyclic Carbenes: A New Generation of Anticancer Agents that Restrain the Growth of High-Grade Serous Ovarian Cancer Tumoroids
Scattolin, Thomas,Bortolamiol, Enrica,Visentin, Fabiano,Palazzolo, Stefano,Caligiuri, Isabella,Perin, Tiziana,Canzonieri, Vincenzo,Demitri, Nicola,Rizzolio, Flavio,Togni, Antonio
, p. 11868 - 11876 (2020)
The first palladium organometallic compounds bearing N-trifluoromethyl N-heterocyclic carbenes have been synthesized. These η3-allyl complexes are potent antiproliferative agents against different cancer lines (for the most part, IC50/sub
N-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist's Toolbox
Schiesser, Stefan,Chepliaka, Hanna,Kollback, Johanna,Quennesson, Thibaut,Czechtizky, Werngard,Cox, Rhona J.
, p. 13076 - 13089 (2020/11/13)
Introducing trifluoromethyl groups is a common strategy to improve the properties of biologically active compounds. However, N-Trifluoromethyl moieties on amines and azoles are very rarely used. To evaluate their suitability in drug design, we synthesized a series of N-Trifluoromethyl amines and azoles, determined their stability in aqueous media, and investigated their properties. We show that N-Trifluoromethyl amines are prone to hydrolysis, whereas N-Trifluoromethyl azoles have excellent aqueous stability. Compared to their N-methyl analogues, N-Trifluoromethyl azoles have a higher lipophilicity and can show increased metabolic stability and Caco-2 permeability. Furthermore, N-Trifluoromethyl azoles can serve as bioisosteres of N-iso-propyl and N-Tert-butyl azoles. Consequently, we suggest that N-Trifluoromethyl azoles are valuable substructures to be considered in medicinal chemistry.
Synthesis and Characterization of N-Trifluoromethyl N-Heterocyclic Carbene Ligands and Their Complexes
Engl, Pascal S.,Senn, Remo,Otth, Elisabeth,Togni, Antonio
, p. 1384 - 1395 (2015/04/27)
Starting from N-trifluoromethyl benzimidazole (1), a series of N-trifluoromethyl benzimidazolium salts 2a-f·HA have been prepared and fully characterized. These were engaged in the formation of [Ir(CO)2(NHC)Cl], [Rh(COD)(NHC)Cl], [Se(NHC)], and
