4-(3-methoxyphenyl)-1-(pyridin-3-yl)piperidine-4-carbonitrile

• 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: 4-(3-methoxyphenyl)-1-(pyridin-3-yl)piperidine-4-carbonitrile
• 英文别名: 1-(pyridin-3-yl)-4-(3-methoxyphenyl)piperidine-4-carbonitrile；1-(3-pyridyl)-4-(3-methoxyphenyl)piperidine-4-carbonitrile；4-(3-methoxyphenyl)-1-pyridin-3-ylpiperidine-4-carbonitrile
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: WBCXSFFVSIWSMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenyl)-1-(pyridin-3-yl)piperidine-4-carbonitrile 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-(4-amino-2,6-diisopropylphenyl)-N’-(1,4-diarylpiperidine-4-yl)methylureas as anti-hyperlipidemic agents

  摘要：

  Based on 1,4-diarylpiperidine-4-methylureas, a new class of ACAT inhibitors, we examined in the study the SAR of a series of compounds prepared by replacing the substituent at the three aromatic parts. Introduction of long alkoxy group onto the phenyl moiety at the B-part was effective in improving both the inhibitory activity for ACAT and the up-regulatory activity for LDL-R expression. Particularly, 3-hydroxy-propoxy group (43) on the phenyl moiety of B-part led to improved solubility, while keeping both biological activities. Compound 43 inhibited ACAT activity with an IC(50) value of 18 nM, which is superior to that of a known ACAT inhibitor, CI-1011. In addition, compound 43 revealed an LDL-R up-regulatory activity comparable to that of SMP-797. We therefore expect this compound to be a novel ACAT inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.059
• 作为产物：
  描述：

  4-(3-methoxyphenyl)-1-(diphenylmethyl)piperidine-4-carbonitrile 在 palladium dihydroxide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 氢气 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 4-(3-methoxyphenyl)-1-(pyridin-3-yl)piperidine-4-carbonitrile
  参考文献：
  名称：

  EP1500648

  摘要：

  公开号：

文献信息

• Novel piperidine derivative
  申请人：Ban Hitoshi

  公开号：US20050165057A1

  公开（公告）日：2005-07-28

  A compound of the formula (1): wherein m and n are independently an integer of 0 to 4, and m+n=4; L is cycloalkyl, substituted cycloalkyl, aromatic group, or substituted aromatic group; Y is aryl or substituted aryl; R is hydrogen, alkyl, etc.; R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are the same or different and are selected, if two or more exist, independently from hydrogen, alkyl, etc., or a prodrug thereof, or a pharmaceutically acceptable salt of the same, which exhibits ACAT inhibitory activity, and is useful as an agent for treatment of hyperlipidemia and atherosclerosis.

  化合物的式子(1): 其中m和n独立地是0到4之间的整数，且m+n=4；L是环烷基，取代环烷基，芳香族基或取代芳香族基；Y是芳基或取代芳基；R是氢，烷基等；R31、R32、R33、R34、R35和R36相同或不同，如果存在两个或更多，则独立地从氢，烷基等中选择，或其前药，或其药学上可接受的盐，其表现出ACAT抑制活性，并且用作治疗高脂血症和动脉粥样硬化的药物。
• NOVEL PIPERIDINE DERIVATIVE
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1500648A1

  公开（公告）日：2005-01-26

  A compound of the formula (1): wherein m and n are independently an integer of 0 to 4, and m+n=4; L is cycloalkyl, substituted cycloalkyl, aromatic group, or substituted aromatic group; Y is aryl or substituted aryl; R is hydrogen, alkyl, etc.; R31, R32, R33, R34, R35 and R36 are the same or different and are selected, if two or more exist, independently from hydrogen, alkyl, etc., or a prodrug thereof, or a pharmaceutically acceptable salt of the same, which exhibits ACAT inhibitory activity, and is useful as an agent for treatment of hyperlipidemia and atherosclerosis.

  式（1）的化合物： 其中 m 和 n 独立地为 0 至 4 的整数，且 m+n=4 ；L 为环烷基、取代环烷基、芳香基团或取代芳香基团；Y 为芳基或取代芳基；R 为氢、烷基等；R31、R32、R33、R34、R35 和 R36 相同或不同，且如果存在两个或多个，则独立地选自氢、烷基等、 或其原药，或其药学上可接受的盐，具有 ACAT 抑制活性，可作为治疗高脂血症和动脉粥样硬化的药物。
• EP1679069
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and structure–activity relationships of N-(4-amino-2,6-diisopropylphenyl)-N’-(1,4-diarylpiperidine-4-yl)methylureas as anti-hyperlipidemic agents
  作者：Shigehiro Asano、Hitoshi Ban、Koichi Kino、Katsuhisa Ioriya、Masami Muraoka

  DOI：10.1016/j.bmc.2009.04.059

  日期：2009.7

  Based on 1,4-diarylpiperidine-4-methylureas, a new class of ACAT inhibitors, we examined in the study the SAR of a series of compounds prepared by replacing the substituent at the three aromatic parts. Introduction of long alkoxy group onto the phenyl moiety at the B-part was effective in improving both the inhibitory activity for ACAT and the up-regulatory activity for LDL-R expression. Particularly, 3-hydroxy-propoxy group (43) on the phenyl moiety of B-part led to improved solubility, while keeping both biological activities. Compound 43 inhibited ACAT activity with an IC(50) value of 18 nM, which is superior to that of a known ACAT inhibitor, CI-1011. In addition, compound 43 revealed an LDL-R up-regulatory activity comparable to that of SMP-797. We therefore expect this compound to be a novel ACAT inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.
• EP1500648
  申请人：——

  公开号：——

  公开（公告）日：——