Synthesis and anti-leukemia activity mensuration of 1-phenethyl-4-hydroxy-4-substituted piperidinium hydrochlorides: Structure of bis[1-phenethyl-4-hydroxy-4-(3-fluorophenyl) piperidinium hydrochloride] studied by X-ray and DFT methods

✍ Scribed by Dingrong Yang; Sijia Xue; Haifeng Wang; Jun Zhu; Jia Jin; Jun Chen

• Publisher: Elsevier Science
• Year: 2009
• Tongue: English
• Weight: 669 KB
• Volume: 929
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2009.04.008

✦ Synopsis

Four unknown compounds have been synthesized based on the molecular motif of 1-phenethyl-4hydroxy 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 ]ÁCH 2 Cl 2 ) via the intermolecular hydrogen bonds. The core of the five-membered structure ([(PHFPH) 2 Cl 2 ]ÁCH 2 Cl 2 ) is formed by two PHFPH cations linked by N(1B)-H(2)Á Á ÁCl(2) hydrogen bonds of lengths 3.033(4), which is engaged in two hydrogen bonds: N(1A)-H(1)Á Á ÁCl(1) of 3.110(4) Å and O(1B)-H(2B)Á Á ÁCl(1) of 3.099(4) Å. 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.