4-哌啶基苯磺酰胺衍生物拮抗剂的合成及表征

Synthesis and Structure Characterization of 4-Piperidyl Benzene Sulfonamide Derivatives Antagonists

趋化因子受体CCR5可作为一种可利用的新靶点,以防治人类HIV感染,非肽类小分子化合物CCR5拮抗剂的研究占居主导地位.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-溴苄基)氧)苯(III),以1-苄基-4-哌啶酮合成了4-甲基-N-丙基-N-(4-哌啶基)苯磺酰胺(IV),通过III、IV合成了一种新的非肽类小分子化合物CCR5拮抗剂N-(5-溴-2-(对氯苄基氧基)苄基)-4-哌啶基)-4-甲基-N-丙基-苯磺酰胺,并对该产物进行了1H NMR、13C NMR及MS表征.

Chemokine receptor CCR5 can be used as a new available target to HIV infection prevention and control of human beings. At present, the peptide of small molecule compounds CCR5 antagonists research occupy the leading position. 4-bromo-2-（ bromomethyl）-1-（ （ 4-chlorobenzyl ） oxy） benzene （Ⅲ ） was synthesized from 1-chloro-4-（chloromethyl）benzene and 5-bromo-2-hydroxybenzaldehyde by elimination reaction, reduction reaction and bromization. 4-methyI-N- （piperidin-4_yl）_N.propylbenzenesulfonarnide （IV） was prepared from 1- benzylpiperidin-4-one. Further reaction of III with IV gave a novel non-peptide CCR5 antagonist N-（L（5- bromo-2- （ （ 4-chlorobenzyl ） oxy ） benzyl ） piperidin-4-yl ）-4-methyl- N-propylbenzenesulfonamide. The compounds were characterized by ^1 HNMR, ^13CNMR and MS.