N-(4-甲基苄基)-3,5-双(4-氯苄叉基)-4-哌啶酮的合成、单晶结构分析以及生物活性的测定

以取代苄胺为原料，经过Michael加成、Dieckmann缩合、水解脱羧、羟醛缩合等反应，合成一个未见文献报道的化合物：N-（4-甲基苄基）-3，5-双（4一氯苄叉基）-4-哌啶酮．目标化合物的结构经元素分析、核磁共振氢谱（^1HNMR）、红外光谱（IR）、质谱（EI-MS）及单晶X-射线衍射测定确定．该单晶属于单斜晶系，空间群为P2（1），α=17．1226（16），b=6．28396（6），c=21．468（2），α／=90°，β=99．753°，y=90°，V=2276．5（4）^3，Z=4，Dc=1．308g／cm^3=0．304mm^-1，M，=448．36，F（000）=936，S=1．019，R=0．0585以及wR=0．1456．目标化合物的结构是非平面的，哌啶环呈沙发构象．化合物中的碳碳双键都是E式构的．在晶体结构中没有分子内和分子间氢键存在．生物活性测试结果表明：目标化合物对白血病K562细胞系的增殖有明显的抑制作用，具有潜在的抗癌活性．

Synthesis, crystal structure and bioactivity of n -( 4 - methylbenzyl ) - 3,5 - bis ( 4 - chlorobenzylide ne ) -4 - piperidone

A novel compound N-(4-methylbenzyl)-3,5-bis(4-chlorobenzylidene)-4-pip-eridone was synthesized with 4-methylbenzylamine as raw materials via a series of Michael addi-tion,Dieckmann condensation,hydrolysis decarboxylation and Aldol condensation.The structure was confirmed by elemental analysis,1H NMR,IR,ESI and single-crystal X-ray diffraction.The crystal belongs to the monoclinic system,with space group P2(1) corresponding to a=17.1226(16),b=6.28396(6),c=21.468(2),α=90°,β=99.753°,γ=90°,V=2276.5(4) 3,Z=4,Dc =1.308 g/cm3=0.304 mm-1,Mr=448.36,F(000)=936,S=1.019,the final R=0.0585 and wR =0.1456.The molecule was nonplanar,and the piperidine ring exhibited a sofa conformation.The carbon-carbon double bonds in the compound were both E-configuration.Neither intranor intermolecular hydrogen bonds was identified in the crystal structure.Assay-based antiproliferative activity study using leukemic cell lines K562 revealed that the compound had high effectiveness in inhibiting leukemia K562 cells proliferation.