4-(4-(3-cyclopentyloxy-4-methoxyphenyl)-4-cyanopiperidin-1-yl)butanoic acid | 401518-43-2

• 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-(4-(3-cyclopentyloxy-4-methoxyphenyl)-4-cyanopiperidin-1-yl)butanoic acid
• 英文别名: 4-[4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]butanoic acid
• CAS: 401518-43-2
• 化学式: C₂₂H₃₀N₂O₄
• 分子量: 386.491
• InChiKey: FCVPZSOWYVVOAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-(3-cyclopentyloxy-4-methoxyphenyl)-4-cyanopiperidin-1-yl)butanoic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4-{4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidin-1-yl}-N-hydroxybutanamide hydrochloride
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors

  摘要：

  The design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors, which possess new templates instead of a cyclohexane ring, are described. The mode of interaction with the enzyme is discussed based on the structure-activity relationship (SAR) data obtained for the synthesized inhibitors. Furthermore, the roles of three pharmacophores, a catechol moiety, a nitrile moiety, and acidic moieties, are discussed using in silico docking studies. More detailed biological evaluations of selected compounds are also presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.040
• 作为产物：
  描述：

  4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidine-4-carbonitrile hydrochloride 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 4-(4-(3-cyclopentyloxy-4-methoxyphenyl)-4-cyanopiperidin-1-yl)butanoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors

  摘要：

  The design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors, which possess new templates instead of a cyclohexane ring, are described. The mode of interaction with the enzyme is discussed based on the structure-activity relationship (SAR) data obtained for the synthesized inhibitors. Furthermore, the roles of three pharmacophores, a catechol moiety, a nitrile moiety, and acidic moieties, are discussed using in silico docking studies. More detailed biological evaluations of selected compounds are also presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.040

文献信息

• PIPERIDINE DERIVATIVES AND DRUGS CONTAINING THESE DERIVATIVES AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1308440B1

  公开（公告）日：2009-05-06
• US7649095B2
  申请人：——

  公开号：US7649095B2

  公开（公告）日：2010-01-19
• Design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors
  作者：Hiroshi Ochiai、Yoshihiko Odagaki、Tazumi Ohtani、Akiharu Ishida、Kensuke Kusumi、Katuya Kishikawa、Susumu Yamamoto、Hiroshi Takeda、Takaaki Obata、Kaoru Kobayashi、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2004.07.040

  日期：2004.10

  The design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors, which possess new templates instead of a cyclohexane ring, are described. The mode of interaction with the enzyme is discussed based on the structure-activity relationship (SAR) data obtained for the synthesized inhibitors. Furthermore, the roles of three pharmacophores, a catechol moiety, a nitrile moiety, and acidic moieties, are discussed using in silico docking studies. More detailed biological evaluations of selected compounds are also presented. (C) 2004 Elsevier Ltd. All rights reserved.