(S)-2-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)propyl 2-hydroxybenzoate | 1454816-27-3

• 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: (S)-2-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)propyl 2-hydroxybenzoate
• 英文别名: [(2S)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl] 2-hydroxybenzoate
• CAS: 1454816-27-3
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: PLLIFMBYXYDNCU-FBXVJESZSA-N

物化性质

• 沸点：
  448.4±15.0 °C(predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)propyl 2-(benzyloxy)benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 (S)-2-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)propyl 2-hydroxybenzoate
  参考文献：
  名称：

  Analogues of the Inhoffen–Lythgoe diol with anti-proliferative activity

  摘要：

  The anti-proliferative activity of a series of ester-and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstrated modest in vitro growth inhibition in two human cancepar cell lines, U87MG (glioblastoma) and HT-29 (colorectal adenocarcinoma). Structureactivity relationship (SAR) studies demonstrated the most active aromatic (13) and aliphatic (25 and 29) substituted analogues were approximately equipotent in U87MG and HT-29 cells. Further evaluation of 13, 25, and 29 indicated these analogues do not activate canonical vitamin D signaling nor antagonize Hedgehog (Hh) signaling. Thus, the cellular mechanism(s) that govern the anti-proliferative activity for this class of truncated vitamin D-based structures appears to be different from classical mechanisms previously identified for these scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.054

文献信息

• Analogues of the Inhoffen–Lythgoe diol with anti-proliferative activity
  作者：Albert M. DeBerardinis、Steven Lemieux、M. Kyle Hadden

  DOI：10.1016/j.bmcl.2013.07.054

  日期：2013.10

  The anti-proliferative activity of a series of ester-and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstrated modest in vitro growth inhibition in two human cancepar cell lines, U87MG (glioblastoma) and HT-29 (colorectal adenocarcinoma). Structureactivity relationship (SAR) studies demonstrated the most active aromatic (13) and aliphatic (25 and 29) substituted analogues were approximately equipotent in U87MG and HT-29 cells. Further evaluation of 13, 25, and 29 indicated these analogues do not activate canonical vitamin D signaling nor antagonize Hedgehog (Hh) signaling. Thus, the cellular mechanism(s) that govern the anti-proliferative activity for this class of truncated vitamin D-based structures appears to be different from classical mechanisms previously identified for these scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.