(S)-5-(4-(1-ethyl-1-[4-((Z)-3-ethyl-3-hydroxy-1-pentenyl)-3-methylphenyl]propyl)-2-methylphenoxy)-4-hydroxypentanoic acid | 1391749-62-4

• 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: (S)-5-(4-(1-ethyl-1-[4-((Z)-3-ethyl-3-hydroxy-1-pentenyl)-3-methylphenyl]propyl)-2-methylphenoxy)-4-hydroxypentanoic acid
• 英文别名: (4S)-5-[4-[3-[4-[(Z)-3-ethyl-3-hydroxypent-1-enyl]-3-methylphenyl]pentan-3-yl]-2-methylphenoxy]-4-hydroxypentanoic acid
• CAS: 1391749-62-4
• 化学式: C₃₁H₄₄O₅
• 分子量: 496.687
• InChiKey: ZBHWQLUYUULCDH-POUWIMNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[1-ethyl-1-(4-ethynyl-3-methylphenyl)-propyl]-2-methylphenol 在 正丁基锂 、 氢气 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (S)-5-(4-(1-ethyl-1-[4-((Z)-3-ethyl-3-hydroxy-1-pentenyl)-3-methylphenyl]propyl)-2-methylphenoxy)-4-hydroxypentanoic acid
  参考文献：
  名称：

  Systematic SAR study of the side chain of nonsecosteroidal vitamin D3 analogs

  摘要：

  A series of nonsecosteroidal vitamin D-3 analogs with carboxylic acid were explored. Through our systematic SAR studies on the side chain moiety, compound 6b was identified as the optimal compound showing excellent vitamin D receptor (VDR) agonistic activity. Compound 6b had the diethyl group in the terminal which was bound by (E)-olefin linker to the bisphenyl core. Calculating the volume of the side chain showed that the diethyl group in 6b filled the hydrophobic region of VDR with the ideal packing coefficient based on the 55% rule, and that this resulted in the most potent in vitro activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.023

文献信息

• Systematic SAR study of the side chain of nonsecosteroidal vitamin D3 analogs
  作者：Hirotaka Kashiwagi、Yoshiyuki Ono、Masateru Ohta、Kenji Morikami、Tadakatsu Takahashi

  DOI：10.1016/j.bmc.2012.05.023

  日期：2012.7

  A series of nonsecosteroidal vitamin D-3 analogs with carboxylic acid were explored. Through our systematic SAR studies on the side chain moiety, compound 6b was identified as the optimal compound showing excellent vitamin D receptor (VDR) agonistic activity. Compound 6b had the diethyl group in the terminal which was bound by (E)-olefin linker to the bisphenyl core. Calculating the volume of the side chain showed that the diethyl group in 6b filled the hydrophobic region of VDR with the ideal packing coefficient based on the 55% rule, and that this resulted in the most potent in vitro activity. (C) 2012 Elsevier Ltd. All rights reserved.