Dingrong Yang, Sijia Xue, Haifeng Wang
Jul 16, 2009
Citations
0
Influential Citations
5
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract Four unknown compounds have been synthesized based on the molecular motif of 1-phenethyl-4-hydroxy piperidinium hydrochloride with a variety of the substituted groups R on the same carbon atom bearing the hydroxy group, such as 3-fluorophenyl ( 3a ), 4-methoxyphenyl ( 3b ), 4-methylphenyl ( 3c ) and cyclohexanyl ( 3d ), and their molecular structures were characterized by 1 H NMR, MS and IR. To account for the stereo structure and provide more information on the effect of counter ions, hydrogen bonds on molecular conformation, the structure of [1-phenethyl-4-hydroxy-4-(3-fluorophenyl) piperidinium hydrochloride] [PHFPH . Cl] 3a was determined by the single-crystal X-ray analysis and optimized by the B3LYP/6-31G (d, p) calculations. Two chloride anions, two PHFPH cations and a dichloromethane molecule formed a five-membered structure ([(PHFPH) 2 Cl 2 ]·CH 2 Cl 2 ) via the intermolecular hydrogen bonds. The core of the five-membered structure ([(PHFPH) 2 Cl 2 ]·CH 2 Cl 2 ) is formed by two PHFPH cations linked by N(1B)–H(2)⋯Cl(2) hydrogen bonds of lengths 3.033(4), which is engaged in two hydrogen bonds: N(1A)–H(1)⋯Cl(1) of 3.110(4) A and O(1B)–H(2B)⋯Cl(1) of 3.099(4) A. The anti-tumor activity tests indicated that these compounds could inhibit the growth of the K562 cells to some extent and have the potential bioactivity of anti-leukemia.