1,1-diphenyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol | 52935-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-diphenyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol
• 英文别名: 1,1-Diphenyl-3-(4-hydroxy-4-phenylpiperidino)-1-propanol；1,1-Diphenyl-3-(4'-phenyl-4'-hydroxy-piperidino)-propanol-(1)；1-(3-hydroxy-3,3-diphenyl-propyl)-4-phenyl-piperidin-4-ol；1-(3-Hydroxy-3,3-diphenylpropyl)-4-phenylpiperidin-4-ol；1-(3-hydroxy-3,3-diphenylpropyl)-4-phenylpiperidin-4-ol
• CAS: 52935-88-3
• 化学式: C₂₆H₂₉NO₂
• 分子量: 387.522
• InChiKey: KNCIWVUTDFSJDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-二苯基-1,3-丙二醇 在 吡啶 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 21.0h， 生成 1,1-diphenyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol
  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

• 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.