(±)-2,3-O-isopropylidene-1,5,6-tri-O-allyl-4-O-benzyl-myo-inositol | 131146-96-8

• 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: (±)-2,3-O-isopropylidene-1,5,6-tri-O-allyl-4-O-benzyl-myo-inositol
• CAS: 131146-96-8
• 化学式: C₂₅H₃₄O₆
• 分子量: 430.541
• InChiKey: VWCAQBIDZZXFKF-PEOLYXCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (±)-2,3-O-isopropylidene-1,5,6-tri-O-allyl-4-O-benzyl-myo-inositol 在 盐酸 、 5%-palladium/activated carbon 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 生成 (±)-1,2,6-tri-O-benzyl-myo-inositol
  参考文献：
  名称：

  Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

  摘要：

  The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poor penetration make it difficult to become a drug used in the clinic. The bioreversible protection technique can enhance membrane penetration characteristics and increase the stability of phosphorylated inositols against enzymatic degradation and is applied widely in drug discovery and development. In this paper, we described the design and synthesis of 22 bioreversible phosphotriester inositols, along with the initial antitumor activity results. Most compounds exhibited significant cytotoxic activity against human cancer cell lines A549, MDA-MB-231 and HeLa, but lower cellular toxicity on normal cell MCF10A in comparison with Cisplatin. These compounds can be used as probes to study the mechanism of intracellular signal transduction mediated by phosphate inositol or as leads of phosphate inositol drugs in the clinic. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.064
• 作为产物：
  描述：

  Inositol 在 sodium hydride 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 14.5h， 生成 (±)-2,3-O-isopropylidene-1,5,6-tri-O-allyl-4-O-benzyl-myo-inositol
  参考文献：
  名称：

  Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

  摘要：

  The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poor penetration make it difficult to become a drug used in the clinic. The bioreversible protection technique can enhance membrane penetration characteristics and increase the stability of phosphorylated inositols against enzymatic degradation and is applied widely in drug discovery and development. In this paper, we described the design and synthesis of 22 bioreversible phosphotriester inositols, along with the initial antitumor activity results. Most compounds exhibited significant cytotoxic activity against human cancer cell lines A549, MDA-MB-231 and HeLa, but lower cellular toxicity on normal cell MCF10A in comparison with Cisplatin. These compounds can be used as probes to study the mechanism of intracellular signal transduction mediated by phosphate inositol or as leads of phosphate inositol drugs in the clinic. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.064

文献信息

• Affinity probes for ins(1,3,4,5)P4 receptors
  作者：Virginia A. Estevez、Glenn D. Prestwich

  DOI：10.1016/s0040-4039(00)74288-2

  日期：1991.3

  A P-1-tethered derivative of Ins(1,3,4,5)P4 was synthesized and used to prepare a bioselective affinity matrix and a photoaffinity label for purification and covalent modification of IP4 receptor proteins.