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The Structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles Related to J147, a Drug for Treating Alzheimer's Disease

The Structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles Related to J147, a Drug for Treating Alzheimer's Disease

M Ángeles Farrán, M Ángels Bonet, Rosa M Claramunt, M Carmen Torralba, Ibon Alkorta, José Elguero

Acta Crystallogr C Struct Chem. 2018 Apr 1;74(Pt 4):513-522.

PMID: 29620036

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP205383171	1,3,5-Triscarboxyphenylethynylbenzene		205383-17-1	Price

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