Farrán M Ángeles, Bonet M Ángels, Claramunt Rosa M, Torralba M Carmen, Alkorta Ibon, Elguero José
Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia, Senda del Rey 9, E-28040 Madrid, Spain.
Departamento de Química Inorgánica, Facultad de Ciencias Químicas, UCM, Ciudad Universitaria s/n, E-28040 Madrid, Spain.
Acta Crystallogr C Struct Chem. 2018 Apr 1;74(Pt 4):513-522. doi: 10.1107/S2053229618004394. Epub 2018 Mar 28.
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 (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.
J147 [N-(2,4-二甲基苯基)-2,2,2-三氟-N'-(3-甲氧基亚苄基)乙酰肼] 最近被报道为一种有前景的治疗阿尔茨海默病的新药。已测定了七种新型1,4-二芳基-5-三氟甲基-1H-1,2,3-三唑的X射线结构，即1-(3,4-二甲基苯基)-4-苯基-5-三氟甲基-1H-1,2,3-三唑（CHFN，1）、1-(3,4-二甲基苯基)-4-(3-甲氧基苯基)-5-三氟甲基-1H-1,2,3-三唑（CHFNO，2）、1-(3,4-二甲基苯基)-4-(4-甲氧基苯基)-5-三氟甲基-1H-1,2,3-三唑（CHFNO，3）、1-(2,4-二甲基苯基)-4-(4-甲氧基苯基)-5-三氟甲基-1H-1,2,3-三唑（CHFNO，4）、1-[2,4-双(三氟甲基)苯基]-4-(3-甲氧基苯基)-5-三氟甲基-1H-1,2,3-三唑（CHFNO，5）、1-(3,4-二甲氧基苯基)-4-(3,4-二甲氧基苯基)-5-三氟甲基-1H-1,2,3-三唑（CHFNO, 6）和3-[4-(3,4-二甲氧基苯基)-5-(三氟甲基)-1H-1,2,3-三唑-1-基]苯酚（CHFNO, 7），并与J147的结构进行了比较。已进行B3LYP/6-311++G(d,p)计算，以确定J147的势能面和分子静电势（MEP），并研究腙J147与均带有CF取代基的1,2,3-三唑之间的相关性。利用分子静电势发现，4的最低能量构象与其X射线结构几乎相同，且与J147的七个最低能量构象之一密切相关。
