(1R,3aR,4S,7aR)-1-((S)-1-azidopropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol | 725227-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3aR,4S,7aR)-1-((S)-1-azidopropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol
• CAS: 725227-37-2
• 化学式: C₁₃H₂₃N₃O
• 分子量: 237.345
• InChiKey: YGILYVPCFHNTKP-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4S,7aR)-1-((S)-1-azidopropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol 在 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2S)-1-[4-(2-hydroxypropan-2-yl)triazol-1-yl]propan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
  参考文献：
  名称：

  Vitamin D and click chemistry. Part 1: A stereoselective route to vitamin D analogues with triazole rings in their side chains

  摘要：

  Efficient preparation of vitamin D CD ring system synthons with triazole rings in their side chains is based on the formation of the triazole ring from a [3+2]-cycloaddition of a vitamin D side chain terminal azide with a terminal acetylene. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.117
• 作为产物：
  描述：

  (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 在 2,6-二甲基吡啶 、 sodium azide 、 氢氟酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1R,3aR,4S,7aR)-1-((S)-1-azidopropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol
  参考文献：
  名称：

  Vitamin D and click chemistry. Part 1: A stereoselective route to vitamin D analogues with triazole rings in their side chains

  摘要：

  Efficient preparation of vitamin D CD ring system synthons with triazole rings in their side chains is based on the formation of the triazole ring from a [3+2]-cycloaddition of a vitamin D side chain terminal azide with a terminal acetylene. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.117

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.