4-[1-(3,4,5-trimethoxybenzyl)-naphtalen-2-yloxy]-but-2-enoic acid | 910296-60-5

• 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: 4-[1-(3,4,5-trimethoxybenzyl)-naphtalen-2-yloxy]-but-2-enoic acid
• 英文别名: 4-[1-(3,4,5-trimethoxybenzoyl)naphthalen-2-yl]oxybut-2-enoic acid
• CAS: 910296-60-5
• 化学式: C₂₄H₂₂O₇
• 分子量: 422.434
• InChiKey: FVWREIUFRQGLFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  正丁胺 、 4-[1-(3,4,5-trimethoxybenzyl)-naphtalen-2-yloxy]-but-2-enoic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以57%的产率得到N-butyl-4-[1-(3,4,5-trimethoxybenzoyl)naphthalen-2-yl]oxybut-2-enamide
  参考文献：
  名称：

  Synthesis of gallic acid based naphthophenone fatty acid amides as cathepsin D inhibitors

  摘要：

  Gallic acid, one of the most abundant plant phenolic acids, has been modified to cathepsin D protease inhibitors. The strategy of modification was proposed basing on some previously reported structure and activity relationship (SAR) studies. The synthesized naphthophenone fatty acid amide derivatives have been evaluated for in vitro cathepsin D inhibition activity. Two of them have shown significant inhibition activity with IC50 values of 0.06 and 0.14 mu M, respectively, as compared against pepstatin (0.0023 mu M), the most potent inhibitor known so far. The study revealed that such attempts on gallic acid based pharmacophores might result in potent inhibitors of cathepsin D. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.010
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸萘-2-基酯 在 氢氧化钾 、 三氯化铝 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 4-[1-(3,4,5-trimethoxybenzyl)-naphtalen-2-yloxy]-but-2-enoic acid
  参考文献：
  名称：

  Synthesis of gallic acid based naphthophenone fatty acid amides as cathepsin D inhibitors

  摘要：

  Gallic acid, one of the most abundant plant phenolic acids, has been modified to cathepsin D protease inhibitors. The strategy of modification was proposed basing on some previously reported structure and activity relationship (SAR) studies. The synthesized naphthophenone fatty acid amide derivatives have been evaluated for in vitro cathepsin D inhibition activity. Two of them have shown significant inhibition activity with IC50 values of 0.06 and 0.14 mu M, respectively, as compared against pepstatin (0.0023 mu M), the most potent inhibitor known so far. The study revealed that such attempts on gallic acid based pharmacophores might result in potent inhibitors of cathepsin D. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.010

文献信息

• Synthesis of a novel plant growth promoter from gallic acid
  作者：Arvind Singh Negi、Mahinder P. Darokar、Sunil K. Chattopadhyay、Ankur Garg、Asish K. Bhattacharya、Vandana Srivastava、Suman P.S. Khanuja

  DOI：10.1016/j.bmcl.2004.11.079

  日期：2005.2

  Gallic acid has been modified to naphthophenone derivatives with esterified fatty acid side chain. Compound 12, an ethyl crotonate ester of naphthophenone derivative has shown potent auxin like growth promoter activity. This is the first example of naphthophenone derivatives with plant growth promoting activity. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of gallic acid based naphthophenone fatty acid amides as cathepsin D inhibitors
  作者：Vandana Srivastava、Hari Om Saxena、Karuna Shanker、J.K. Kumar、Suaib Luqman、M.M. Gupta、S.P.S. Khanuja、Arvind S. Negi

  DOI：10.1016/j.bmcl.2006.06.010

  日期：2006.9

  Gallic acid, one of the most abundant plant phenolic acids, has been modified to cathepsin D protease inhibitors. The strategy of modification was proposed basing on some previously reported structure and activity relationship (SAR) studies. The synthesized naphthophenone fatty acid amide derivatives have been evaluated for in vitro cathepsin D inhibition activity. Two of them have shown significant inhibition activity with IC50 values of 0.06 and 0.14 mu M, respectively, as compared against pepstatin (0.0023 mu M), the most potent inhibitor known so far. The study revealed that such attempts on gallic acid based pharmacophores might result in potent inhibitors of cathepsin D. (c) 2006 Elsevier Ltd. All rights reserved.