N-propyl-4-(4-chlorophenyl)-4-piperidinol

• 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: N-propyl-4-(4-chlorophenyl)-4-piperidinol
• 英文别名: Propyl-4-hydroxy-4-(4-chlorophenyl) piperidine；4-(4-chlorophenyl)-1-propylpiperidin-4-ol
• 化学式: C₁₄H₂₀ClNO
• mdl: MFCD13166893
• 分子量: 253.772
• InChiKey: WRHFBZUNRJVEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-氯苯基)-4-羟基哌啶 、 溴丙烷 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以49%的产率得到N-propyl-4-(4-chlorophenyl)-4-piperidinol
  参考文献：
  名称：

  Synthesis of 4-Arylpiperidin-4-ol Derivatives of Loperamide as Agents with Potent Antiproliferative Effects against HCT-116 and HL-60 Cells

  摘要：

  The structure of 4-arylpiperidin-4-ol, a constituent of the antidiarrheal loperamide, is key to v. opioid receptor activation. Some opioid derivatives were recently reported to induce tumor cell death, but the chemical structures responsible for their antitumor activity remain unclear. We synthesized loperamide analogs and tested their antiproliferative activity against HCT-116 colon tumor cells and HL-60 leukemia cells. The N-substituents on 4-arylpiperidin-4-ol units were found to play an important role in their antiproliferative activity, and the N-diphenylpropanol analogs exhibited the most potent antiproliferative activity. Furthermore, the N-diphenylpropanol analog activated caspase-3, as was found previously for opioids that exhibited antitumor effects.

  DOI：

  10.3987/com-13-s(s)20

文献信息

• CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREOF
  申请人：Luly Jay R.

  公开号：US20120046311A1

  公开（公告）日：2012-02-23

  Disclosed are novel compounds and a method of treating a disease associated with aberrant leukocyte recruitment and/or activation. The method comprises administering to a subject in need an effective amount of a compound represented by: or physiologically acceptable salt thereof.

  本发明涉及新化合物和治疗与异常白细胞招募和/或激活相关的疾病的方法。该方法包括向需要治疗的受试者施用有效量的以下化合物或其生理上可接受的盐：（图片无法显示，请见谅）
• CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREFOR
  申请人：MILLENNIUM PHARMACEUTICALS, INC.

  公开号：EP1204665B1

  公开（公告）日：2009-01-07
• US7271176B2
  申请人：——

  公开号：US7271176B2

  公开（公告）日：2007-09-18
• US7541365B2
  申请人：——

  公开号：US7541365B2

  公开（公告）日：2009-06-02
• Synthesis of 4-Arylpiperidin-4-ol Derivatives of Loperamide as Agents with Potent Antiproliferative Effects against HCT-116 and HL-60 Cells
  作者：Noriyuki Hatae、Tatsunori Iwamura、Tomoyuki Nagayama、Hiroyoshi Esaki、Eiko Kujime、Masabumi Minami、Minoru Ishikura、Tominari Choshi、Satoshi Hibino、Chiaki Okada、Eiko Toyota、Hideko Nagasawa

  DOI：10.3987/com-13-s(s)20

  日期：——

  The structure of 4-arylpiperidin-4-ol, a constituent of the antidiarrheal loperamide, is key to v. opioid receptor activation. Some opioid derivatives were recently reported to induce tumor cell death, but the chemical structures responsible for their antitumor activity remain unclear. We synthesized loperamide analogs and tested their antiproliferative activity against HCT-116 colon tumor cells and HL-60 leukemia cells. The N-substituents on 4-arylpiperidin-4-ol units were found to play an important role in their antiproliferative activity, and the N-diphenylpropanol analogs exhibited the most potent antiproliferative activity. Furthermore, the N-diphenylpropanol analog activated caspase-3, as was found previously for opioids that exhibited antitumor effects.