1-(3',4',5'-trimethoxybenzoyl)naphthalene 2-O-acetic acid | 850146-73-5

• 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: 1-(3',4',5'-trimethoxybenzoyl)naphthalene 2-O-acetic acid
• 英文别名: 2-[1-(3,4,5-Trimethoxybenzoyl)naphthalen-2-yloxy]ethanoic acid；2-[1-(3,4,5-trimethoxybenzoyl)naphthalen-2-yl]oxyacetic acid
• CAS: 850146-73-5
• 化学式: C₂₂H₂₀O₇
• 分子量: 396.397
• InChiKey: GKSMDAOMTBHTCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3',4',5'-trimethoxybenzoyl)naphthalene 2-O-acetic acid 在 3,4,5-三甲氧基苯胺 TEA 、 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 2.0h， 以89%的产率得到1-(3,4,5-Trimethoxy-phenyl)-naphtho[2,1-b]furan
  参考文献：
  名称：

  Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan as a novel anticancer agent

  摘要：

  3',4',5'-Trimethoxy benzoyl-naphthalene 2-O-acetic acid (5) underwent base catalysed intramolecular condensation to yield exclusively 1-(3',4',5'-trimethoxy) phenyl naphtho[2,1-b]furan 8. The cyclised product 8 has been characterised by spectroscopy. The product 8 showed significant anticancer activity against human cancer cell lines COLO320DM (colon), CaCO2 (colon) and WRL68 (liver) at 0.7, 0.65 and 0.50 mu g/ml concentrations, respectively, in the in vitro MTT assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.105
• 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 4.0h， 生成 1-(3',4',5'-trimethoxybenzoyl)naphthalene 2-O-acetic 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

• A Simple Regioselective Demethylation of <i>p</i>‐Aryl Methyl Ethers Using Aluminum Chloride‐Dichloromethane System
  作者：Arvind S. Negi、Sunil K. Chattopadhyay、Sachin Srivastava、Asish K. Bhattacharya

  DOI：10.1081/scc-200046477

  日期：2005.1.1

  Abstract Several aryl methyl ethers of phenolic esters and diaryl ketones have been selectively demethylated to their corresponding 4‐hydroxy derivatives by using aluminium chloride‐dichloromethane system at room temperature in good yields (53–85%).

  摘要 在室温下，通过使用氯化铝-二氯甲烷体系，酚酯和二芳基酮的几种芳基甲基醚以良好的产率（53-85%）选择性地脱甲基为相应的 4-羟基衍生物。
• 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.
• Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan as a novel anticancer agent
  作者：Vandana Srivastava、Arvind S. Negi、J.K. Kumar、Uzma Faridi、Brijesh S. Sisodia、M.P. Darokar、Suaib Luqman、S.P.S. Khanuja

  DOI：10.1016/j.bmcl.2005.10.105

  日期：2006.2

  3',4',5'-Trimethoxy benzoyl-naphthalene 2-O-acetic acid (5) underwent base catalysed intramolecular condensation to yield exclusively 1-(3',4',5'-trimethoxy) phenyl naphtho[2,1-b]furan 8. The cyclised product 8 has been characterised by spectroscopy. The product 8 showed significant anticancer activity against human cancer cell lines COLO320DM (colon), CaCO2 (colon) and WRL68 (liver) at 0.7, 0.65 and 0.50 mu g/ml concentrations, respectively, in the in vitro MTT assay. (c) 2005 Elsevier Ltd. All rights reserved.