(S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxymethyl-3H-isobenzofuran-1-one | 721449-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxymethyl-3H-isobenzofuran-1-one
• CAS: 721449-05-4
• 化学式: C₂₃H₃₀O₅Si
• 分子量: 414.574
• InChiKey: PUIVJZUASQPMKN-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxymethyl-3H-isobenzofuran-1-one 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 生成 3,5-Di-tert-butyl-benzoic acid (S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of new isobenzofuranone ligands of protein kinase C

  摘要：

  Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. We have designed novel PKC ligands having an isobenzofuranone template, based on the proposed interaction of DAG (1,2-diacyl-sn-glycerol) with the PKCdelta C1B ligand-binding domain. Several isobenzofuranone derivatives were synthesized and their PKCalpha binding activities were evaluated. The pivaloyl derivative 1f was found to be a strong PKCalpha ligand, and the structure-activity relationship is well explained by our proposed binding model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.097
• 作为产物：
  描述：

  3,3-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-hydroxy-3H-isobenzofuran-1-one 在 咪唑 、 potassium carbonate 、 氟化氢吡啶 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.0h， 生成 (S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxymethyl-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of new isobenzofuranone ligands of protein kinase C

  摘要：

  Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. We have designed novel PKC ligands having an isobenzofuranone template, based on the proposed interaction of DAG (1,2-diacyl-sn-glycerol) with the PKCdelta C1B ligand-binding domain. Several isobenzofuranone derivatives were synthesized and their PKCalpha binding activities were evaluated. The pivaloyl derivative 1f was found to be a strong PKCalpha ligand, and the structure-activity relationship is well explained by our proposed binding model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.097

文献信息

• Evaluation of series of isobenzofuranone dimers as PKCα ligands: implication for the distance between the two ligand binding sites
  作者：Yoshiyasu Baba、Satoshi Mayumi、Go Hirai、Hidekazu Kawasaki、Yosuke Ogoshi、Takeshi Yanagisawa、Yuichi Hashimoto、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2004.02.098

  日期：2004.6

  Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. To examine the distance between the two ligand binding sites (C1A and C1B) of PKC, we designed and synthesized two series of isobenzofuranone dimers. Peak binding activities were observed for the C3-acyl chain dimers having a C-10-C-12 linker and for the C7 dimers having a C-14-C-16. (C) 2004 Elsevier Ltd. All rights reserved.