N-烯丙基-N-(1-(5-溴-2-(对氯苄基氧基)苄基)-4-哌啶基)苯甲酰胺的合成及表征  

Synthesis and Structure Characterization of N-allyl-N-(1-(5-bromo-2-((4-chlorobenzyl)oxy)benzyl)piperidin-4-yl)benzamide

作　　者：程德军[1] 黄斌[1] 李明田[1] 

机构地区：[1]四川理工学院材料与化学工程学院,四川自贡643000

出　　处：《安徽师范大学学报（自然科学版）》2014年第6期559-563,共5页Journal of Anhui Normal University(Natural Science)

基　　金：国家自然科学基金(51303115)

摘　　要：趋化因子受体CCR5是HIV-1病毒进入人体细胞的主要辅助受体,CCR5拮抗剂可作为一种靶向制剂,以防治人类HIV-1感染.目前,非肽类小分子化合物CCR5拮抗剂的研究占据主导地位.本文以5-溴水杨醛、4-氯苄氯为原料,通过消去、还原及溴化合成了4-溴-2-溴甲基-1-((4-氯苄基)氧)苯(中间体3),以1-苄基-4-哌啶酮合成了N-烯丙基-N-(4-哌啶基)苯甲酰胺,通过中间体3、中间体7合成了一种有望用作CCR5拮抗剂的新的非肽类小分子化合物N-烯丙基-N-(1-(5-溴-2-(对氯苄基氧基)苄基)-4-哌啶基)苯甲酰胺,该产物有一定的生物活性,并对该产物进行了1 H NMR、13C NMR、IR及MS表征.Chemokine receptor CCR5 is a major coreceptor for HIV-1entry into cell and CCR5 antagonists can be used as a targeting preparation in the prevention of human HIV-1infection.At present,the peptide of small molecule compounds CCR5 antagonists research occupy the leading position.4-bromo-2-（bromomethyl）-1-（（4-chlorobenzyl）oxy）benzene（intermediate 3）was synthesized from 1-chloro-4-（chloromethyl）benzene and 5-bromo-2-hydroxybenzaldehyde by elimination reaction,reduction reaction and bromination.N-allyl-N-（piperidin-4-yl）benzamide was prepared from 1-benzylpiperidin-4-one.Further reaction of intermediate 3with intermediate 7gave a novel non-peptide CCR5 antagonist N-allyl-N-（1-（5-bromo-2-（（4-chlorobenzyl）oxy）benzyl）piperidin-4-yl）benzamide.The product has a certain biological activity.The compounds were characterized by 1 H NMR,13 C NMR,IR and MS.

关 键 词：CCR5拮抗剂 非肽类小分子化合物 表征 合成 

分 类 号：O621.3[理学—有机化学]