5-hydroxy-1-(4-hydroxyphenyl)-11-phenylundecan-3-one | 1360875-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-hydroxy-1-(4-hydroxyphenyl)-11-phenylundecan-3-one
• CAS: 1360875-02-0
• 化学式: C₂₃H₃₀O₃
• 分子量: 354.489
• InChiKey: XDTCCLMIQQZZNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-1-(4-hydroxyphenyl)-11-phenylundecan-3-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以40%的产率得到(E)-1-(4-hydroxyphenyl)-11-phenylundec-4-en-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators

  摘要：

  In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, a series of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.113
• 作为产物：
  描述：

  7-phenylheptanal 在 四丁基氟化铵 、 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 5-hydroxy-1-(4-hydroxyphenyl)-11-phenylundecan-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators

  摘要：

  In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, a series of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.113

文献信息

• Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators
  作者：Enrico Morera、Luciano De Petrocellis、Ludovica Morera、Aniello Schiano Moriello、Marianna Nalli、Vincenzo Di Marzo、Giorgio Ortar

  DOI：10.1016/j.bmcl.2011.12.113

  日期：2012.2

  In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, a series of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d). (C) 2011 Elsevier Ltd. All rights reserved.