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Title

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

AuthorsFarrán, M. Ángeles; Bonet, Maria Angels; Claramunt, Rosa M.; Torralba, M. Carmen; Alkorta, Ibon ; Elguero, José
KeywordsJ147
Molecular electrostatic potentials
Alzheimer’s disease
1,2,3-triazoles
Crystal structure
DFT calculations
Issue Date2018
PublisherWiley-VCH
CitationActa Crystallographica Section C: Structural Chemistry 74: 513-522 (2018)
AbstractJ147 [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 (CHFN, 1), 1-(3,4-dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 2), 1-(3,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 3), 1-(2,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 4), 1-[2,4-bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 5), 1-(3,4-dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 6) and 3-[4-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenol (CHFNO, 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 CF 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.
URIhttp://hdl.handle.net/10261/165639
DOIhttp://dx.doi.org/10.1107/S2053229618004394
Identifiersdoi: 10.1107/S2053229618004394
issn: 2053-2296
Appears in Collections:(IQM) Artículos
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