(E)-(2-(hydroxymethyl)-4-(8-(nonyloxy)octylidene)-5-oxotetrahydrofuran-2-yl)methyl pivalate | 1219016-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (E)-(2-(hydroxymethyl)-4-(8-(nonyloxy)octylidene)-5-oxotetrahydrofuran-2-yl)methyl pivalate
• 英文别名: [(4E)-2-(hydroxymethyl)-4-(8-nonoxyoctylidene)-5-oxooxolan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1219016-29-1
• 化学式: C₂₈H₅₀O₆
• 分子量: 482.701
• InChiKey: CYYWCMKXPXJMRW-HKOYGPOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [5-Oxo-2-(phenylmethoxymethyl)oxolan-2-yl]methyl 2,2-dimethylpropanoate 、 在 lithium hexamethyldisilazane 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-(2-(hydroxymethyl)-4-(8-(nonyloxy)octylidene)-5-oxotetrahydrofuran-2-yl)methyl pivalate
  参考文献：
  名称：

  Polar 3-alkylidene-5-pivaloyloxymethyl-5′-hydroxymethyl-γ-lactones as protein kinase C ligands and antitumor agents

  摘要：

  A series of DAG-lactones with polar 3-alkylidene substituents have been investigated as PKC-alpha ligands and antitumor agents. Extensive analysis of structure-activity relationships for the 3-alkylidene chain revealed that polar groups such as ether, hydroxyl, aldehyde, ester, acyloxy, and amido were tolerated with similar binding affinities and reduced lipophilicities compared to the corresponding unsubstituted alkylidene chain. Among the derivatives, compounds 5, 6 and 8 with an ether type of side chain showed high binding affinities in range of K-i = 3-5 nM and excellent antitumor profiles, particularly against the colo205 colon cancer and the K562 leukemia cell lines. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.058

文献信息

• Polar 3-alkylidene-5-pivaloyloxymethyl-5′-hydroxymethyl-γ-lactones as protein kinase C ligands and antitumor agents
  作者：Ji-Hye Kang、Yerim Kim、Shin-Hye Won、Song-Kyu Park、Chang Woo Lee、Hwan-Mook Kim、Nancy E. Lewin、Nicholas A. Perry、Larry V. Pearce、Daniel J. Lundberg、Robert J. Surawski、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2009.12.058

  日期：2010.2

  A series of DAG-lactones with polar 3-alkylidene substituents have been investigated as PKC-alpha ligands and antitumor agents. Extensive analysis of structure-activity relationships for the 3-alkylidene chain revealed that polar groups such as ether, hydroxyl, aldehyde, ester, acyloxy, and amido were tolerated with similar binding affinities and reduced lipophilicities compared to the corresponding unsubstituted alkylidene chain. Among the derivatives, compounds 5, 6 and 8 with an ether type of side chain showed high binding affinities in range of K-i = 3-5 nM and excellent antitumor profiles, particularly against the colo205 colon cancer and the K562 leukemia cell lines. (c) 2010 Elsevier Ltd. All rights reserved.