3-acetyloxybenzyl diethylphosphate | 1118974-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-acetyloxybenzyl diethylphosphate
• 英文别名: [3-(diethoxyphosphoryloxymethyl)phenyl] acetate
• CAS: 1118974-23-4
• 化学式: C₁₃H₁₉O₆P
• 分子量: 302.264
• InChiKey: MSWXWTRTBVYCMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羟基苯甲醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 3-acetyloxybenzyl diethylphosphate
  参考文献：
  名称：

  Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents

  摘要：

  Several acetyl-protected hydroxybenzyl diethyl phosphates (EHBPs) that are capable of forming quinone methide intermediates were synthesized and their cell growth inhibitory properties were evaluated in four different human cancer cell lines. Compounds 1, 1a, and 1b, corresponding to (4-acetyloxybenzyl diethylphosphate), (3-methyl-4-acetyloxybenzyl diethylphosphate), and (3-chloro-4-acetyloxybenzyl diethylphosphate), were significantly more potent than compounds 2 and 3, (2-acetyloxybenzyl diethylphosphate) and (3-acetyloxybenzyl diethylphosphate), respectively. Using HT-29 human colon cancer cells, compounds 1 and 3 increased apoptosis, inhibited proliferation, and caused a G(2)/M block in the cell cycle. Our data suggest that these compounds merit further investigation as potential anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.075

文献信息

• Anti-Inflammatory Compounds and Uses Thereof
  申请人：Rigas Basil

  公开号：US20090099137A1

  公开（公告）日：2009-04-16

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.
• ANTI-INFLAMMATORY COMPOUNDS AND USES THEREOF
  申请人：RIGAS Basil

  公开号：US20120316139A1

  公开（公告）日：2012-12-13

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also disclosed.
• Anti-Inflammatory Compounds and Use Thereof
  申请人：Rigas Basil

  公开号：US20160243137A1

  公开（公告）日：2016-08-25

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also disclosed.
• US8236820B2
  申请人：——

  公开号：US8236820B2

  公开（公告）日：2012-08-07
• Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents
  作者：Ravinder Kodela、Mitali Chattopadhyay、Niharika Nath、Lucyna Z. Cieciura、Liliya Pospishill、Daniel Boring、James A. Crowell、Khosrow Kashfi

  DOI：10.1016/j.bmcl.2011.09.075

  日期：2011.12

  Several acetyl-protected hydroxybenzyl diethyl phosphates (EHBPs) that are capable of forming quinone methide intermediates were synthesized and their cell growth inhibitory properties were evaluated in four different human cancer cell lines. Compounds 1, 1a, and 1b, corresponding to (4-acetyloxybenzyl diethylphosphate), (3-methyl-4-acetyloxybenzyl diethylphosphate), and (3-chloro-4-acetyloxybenzyl diethylphosphate), were significantly more potent than compounds 2 and 3, (2-acetyloxybenzyl diethylphosphate) and (3-acetyloxybenzyl diethylphosphate), respectively. Using HT-29 human colon cancer cells, compounds 1 and 3 increased apoptosis, inhibited proliferation, and caused a G(2)/M block in the cell cycle. Our data suggest that these compounds merit further investigation as potential anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.