Crystal Structures of 2-Phenyl-2H-1,2,3-Triazol-4-Carbaldehyde, an Active α-Glycosidase Inhibition Agent, and (1-Phenyl-1H-1,2,3-Triazol-4-yl)Methyl Benzoate and (2-(4-Fluorophenyl)-2H-1,2,3-Triazole-4-yl)Methanol, Two Moderately Active Compounds

Abstract

The crystal structures of (1-phenyl-1H-1,2,3-triazol-4-yl)methyl benzoate, 1a, (2-(4-fluorophenyl)-2H-1,2,3-triazole-4-yl)methanol, 2a, and 2-phenyl-2H-1,2,3-triazol-4-carbaldehyde, 2b, are reported. Compounds 1a and 2a were recently reported to exhibit mild a-glycosidase inhibition activity, while compound 2b exhibited a much greater activity. Only small dihedral angles 6.52(4), 14.02(10) and 2.44(7)°are present between the triazolyl ring and the attached aryl rings in 1a, 2a and 2b, respectively. The relatively flat compounds 2a and 2b contrast with compound 1a, which is ''V'' shaped, with a dihedral angle between the near planar phenyltriazolyl-CH 2 and phenyl-CO 2 CH 2 moieties of 88.11(4)°. The intermolecular interactions in 1a are C-HÁÁÁX (X = N or p(triazole) and p(triazole) ÁÁÁp ( Graphical Abstract The relatively flat compounds, (2-(4-fluorophenyl)-2H-1,2,3-triazole-4-yl)methanol and 2-phenyl-2H-1,2,3-triazol-4-carbaldehyde, contrast with compound (1-phenyl-1H-1,2,3-triazol-4-yl)methyl benzoate, which is ''V'' shaped, with a dihedral angle between the near planar phenyltriazolyl-CH2 and phenyl-CO2CH2 moieties of 88.11(4) o.