The structures of 1,4‐diaryl‐5‐trifluoromethyl‐1H‐1,2,3‐triazoles related to J147, a drug for treating Alzheimer's disease

J147 [N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N′-(3-methoxybenzylidene)acetohydrazide] has recently been reported as a promising new drug for the treatment of Alzheimer's disease. The X-ray structures of seven new 1,4-diaryl-5-tri­fluoro­methyl-1H-1,2,3-triazoles, namely 1-(3,4-di­methyl­phen­yl)-4-phenyl-5-tri­fluoro­methyl-1H-1,2,3-triazole (C17H14F3N3, 1), 1-(3,4-di­methyl­phen­yl)-4-(3-meth­oxy­phen­yl)-5-tri­fluoro­methyl-1H-1,2,3-triazole (C18H16F3N3O, 2), 1-(3,4-di­methyl­phen­yl)-4-(4-meth­oxy­phen­yl)-5-tri­fluoro­methyl-1H-1,2,3-triazole (C18H16F3N3O, 3), 1-(2,4-di­­methyl­phen­yl)-4-(4-meth­oxy­phen­yl)-5-tri­fluoro­methyl-1H-1,2,3-triazole (C18H16F3N3O, 4), 1-[2,4-bis­(tri­fluoro­meth­yl)phen­yl]-4-(3-methoxy­phen­yl)-5-tri­fluoro­methyl-1H-1,2,3-triazole (C18H10F9N3O, 5), 1-(3,4-di­meth­oxy­phen­yl)-4-(3,4-di­meth­oxy­phen­yl)-5-tri­fluoro­methyl-1H-1,2,3-triazole (C19H18F3N3O4, 6) and 3-[4-(3,4-di­meth­oxy­phen­yl)-5-(tri­fluoro­meth­yl)-1H-1,2,3-triazol-1-yl]phenol (C17H14F3N3O3, 7), have been determined and compared to that of J147. B3LYP/6-311++G(d,p) calculations have been performed to determine the potential surface and mol­ecular electrostatic potential (MEP) of J147, and to examine the correlation between hydrazone J147 and the 1,2,3-triazoles, both bearing a CF3 substituent. Using MEPs, it was found that the minimum-energy conformation of 4, which is nearly identical to its X-ray structure, is closely related to one of the J147 seven minima.