4-甲基-N-烯丙基-N-(1-(5-溴-2-(对氯苄基氧基)苄基)-4-哌啶基)苯磺酰胺的合成及生物活性研究  

Synthesis and biological activities of N-allyl-N-(1-(5-bromo-2-((4-chlorobenzyl)oxy)benzyl)piperidin-4-yl)-4-methylbenzenesulfonamide

作　　者：黄斌[1] 程德军[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：《西北师范大学学报（自然科学版）》2015年第4期58-61,85,共5页Journal of Northwest Normal University(Natural Science)

基　　金：四川省教育厅基金资助项目(15ZB0215);自贡市重点科技计划项目(2014ZC01)

摘　　要：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4-甲基-N-烯丙基-N-(4-哌啶基)苯磺酰胺(中间体7),通过中间体3和7合成了一种新的非肽类CCR5拮抗剂4-甲基-N-烯丙基-N-(1-(5-溴-2-(对氯苄基氧基)苄基)-4-哌啶基)苯磺酰胺,并对产物进行了1 HNMR,13 CNMR,IR,MS表征及生物活性检测.结果表明,该拮抗剂合成总产率约为26.0%,具有较好的生物活性.4-Bromo-2-（bromomethyl）-1-（（4-chlorobenzyl）oxy）benzene（intermediate 3）is synthesized from 1-chloro-4-（chloromethyl）benzene and 5-bromo-2-hydroxybenzaldehyde by elimination reaction,reduction reaction and bromization in turn. N-allyl-4-methyl-N-（piperidin-4-yl）benzenesulfonamide（intermediate 7）is prepared from 1-benzylpiperidin-4-one.Further reaction of intermediate 3 with intermediate 7 can give a novel non-peptide CCR5 antagonist N-allyl-N-（1-（5-bromo-2-（（4-chlorobenzyl）oxy）benzyl）piperidin-4-yl）-4-methyl benzenesulfonamide.The compounds are characterized by ^1HNMR,^13CNMR,IR,MS.The biological activity of the antagonist is detected.The results show that the antagonist is the target peoduct with good biological activity and the total yield is about 26%.

关 键 词：CCR5拮抗剂 苯磺酰胺 非肽类小分子化合物 生物活性 

分 类 号：O621.3[理学—有机化学] R914[理学—化学]