1-benzyl-4-(3-bromopropyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-4-(3-bromopropyl)piperidine
• 化学式: C₁₅H₂₂BrN
• 分子量: 296.25
• InChiKey: WMUQBTCPHHEEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-(3-bromopropyl)piperidine 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3-(1-benzylpiperidin-4-yl)propan-1-amine
  参考文献：
  名称：

  M2 Subtype preferring dibenzodiazepinone-type muscarinic receptor ligands: Effect of chemical homo-dimerization on orthosteric (and allosteric?) binding

  摘要：

  A series of new dibenzodiazepinone-type muscarinic receptor ligands, including two homo-dimeric compounds, was prepared. Sixteen representative compounds were characterized in equilibrium binding studies with [H-3]N-methylscopolamine ([H-3]NMS) at the muscarinic receptor subtype M-2, and seven selected compounds were additionally investigated at M-1, M-3, M-4 and M-5 with respect to receptor subtype selectivity. The side chain of the known M-2 preferring muscarinic receptor antagonist DIBA was widely varied with respect to chain length and type of the basic group (amine, imidazole, guanidine and piperazine). Most of the structural changes were well tolerated with respect to muscarinic receptor binding, determined by displacement of [H-3]NMS. Compounds investigated at all subtypes shared a similar selectivity profile, which can be summarized as M-2 > M-1 approximate to M-4 > M-3 approximate to M-5 (46, 50, 57, 62-64) and M-2 > M-1 approximate to M-4 > M-3 > M-5 (1, 58). The homo-dimeric dibenzodiazepinone derivatives UNSW-MK250 (63) and UNSW-MK262 (64) exhibited the highest M-2 receptor affinities (pIC(50) = 9.0 and 9.2, respectively). At the M-2 receptor a steep curve slope of -2 was found for the dimeric ligand 63, which cannot be described according to the law of mass action, suggesting a more complex mechanism of binding. In addition to equilibrium binding studies, for selected ligands, we determined pEC(50,diss), an estimate of affinity to the allosteric site of M-2 receptors occupied with [H-3]NMS. Compounds 58 and 62-64 were capable of retarding [H-3]NMS dissociation by a factor > 10 (E-max,E-diss >92%), with highest potency (pEC(50,diss) = 5.56) residing in the dimeric compound 64. As the monomeric counterpart of 64 was 100 times less potent (62: pEC(50),(diss) = 3.59), these data suggest that chemical dimerization of dibenzodiazepinone-type M receptor ligands can enhance allosteric binding. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.015
• 作为产物：
  描述：

  3-(1-Benzyl-piperidin-4-yl)-propan-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到1-benzyl-4-(3-bromopropyl)piperidine
  参考文献：
  名称：

  新型胆碱酯酶抑制剂 酞菁-1（2 H）-一衍生物的合成，生物学评估和分子建模研究†

  摘要：

  设计并合成了一种新的基于酞菁-1（2 H）-一个支架的多奈哌齐类似物系列，旨在探索其作为人ChEIs的潜力。生物学结果表明，提出的结构修饰显着影响了ChE抑制能力以及对AChE / BuChE的选择性。化合物1d在μM范围内均显示出对这两种酶的体外抑制作用。但是，大多数目标化合物对AChE的活性均显着高于BuChE，特别是1f，1h和1j，IC 50。值在低微摩尔或亚微摩尔范围内，是系列中活性最高的化合物。对接模拟表明，活性最高的化合物可以使用类似的相互作用网络识别多奈哌齐结合位点。这些结果使我们能够合理化观察到的结构-活性关系。此外，预测的理化和ADME性质也与多奈哌齐相当。

  DOI：

  10.1039/c6ra03841g

文献信息

• Piperidine derivate, its use and pharmaceutical composition containing it
  申请人：Eisai Co., Ltd.

  公开号：EP0229391A1

  公开（公告）日：1987-07-22

  A novel piperidine derivative as defined by the formula (I), including a salt thereof, wherein R1, X, A and R2 have the aforementioned meanings. Further, pharmaceutical compositions containing the same and the use of the piperidine derivatives for the making of such compositions preventing dementias and sequelae of cerebrovascular disease is disclosed.

  本发明公开了一种由式（I）定义的新型哌啶衍生物，包括其盐，其中 R1、X、A 和 R2 具有上述含义。 此外，本发明还公开了含有该衍生物的药物组合物，以及该哌啶衍生物在制作此类组合物中用于预防痴呆症和脑血管疾病后遗症的用途。
• SUGIMOTO, HACHIRO;NAKAMURA, TAKAHARU;TSUCHIYA, YUTAKA;SUGUMI, HIROYUKI;HI+
  作者：SUGIMOTO, HACHIRO、NAKAMURA, TAKAHARU、TSUCHIYA, YUTAKA、SUGUMI, HIROYUKI、HI+

  DOI：——

  日期：——
• US4849431A
  申请人：——

  公开号：US4849431A

  公开（公告）日：1989-07-18
• US4942169A
  申请人：——

  公开号：US4942169A

  公开（公告）日：1990-07-17
• US5118684A
  申请人：——

  公开号：US5118684A

  公开（公告）日：1992-06-02