6-Chloro-2-oxo-2H-chromene-3-carboxylic acid hydroxyamide | 742503-72-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-Chloro-2-oxo-2H-chromene-3-carboxylic acid hydroxyamide
• 英文别名: 6-chloro-N-hydroxy-2-oxochromene-3-carboxamide
• CAS: 742503-72-6
• 化学式: C₁₀H₆ClNO₄
• 分子量: 239.615
• InChiKey: HYUAUCQWRCSYLQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-oxo-2H-chromene-3-carboxylic acid hydroxyamide 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 6-chlorocoumarin-3-carboxylic acid
  参考文献：
  名称：

  Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study

  摘要：

  A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, displaying pIC(50) values of particular interest: 2a shows pIC(50) 7.76 and a selectivity index (pS.I.) 2.94 and 2b shows pIC(50) 7.72 and a pS.I. of 2.80. The coumarin-3-acyl chlorides 3a-e showed high pIC(50) values against both MAO-A and MAO-B isoforms, 3d being the highest against MAO-B with a pIC(50) value of 8.00. In order to rationalize the activity/selectivity results, molecular descriptors were generated. Further insight about enzyme-inhibitor interaction was obtained by docking experiments with the MAO-B isoform. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.010
• 作为产物：
  描述：

  5-氯代水杨醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙腈 为溶剂， 生成 6-Chloro-2-oxo-2H-chromene-3-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study

  摘要：

  A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, displaying pIC(50) values of particular interest: 2a shows pIC(50) 7.76 and a selectivity index (pS.I.) 2.94 and 2b shows pIC(50) 7.72 and a pS.I. of 2.80. The coumarin-3-acyl chlorides 3a-e showed high pIC(50) values against both MAO-A and MAO-B isoforms, 3d being the highest against MAO-B with a pIC(50) value of 8.00. In order to rationalize the activity/selectivity results, molecular descriptors were generated. Further insight about enzyme-inhibitor interaction was obtained by docking experiments with the MAO-B isoform. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.010

文献信息

• Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Olivia Befani、Paola Turini、Stefano Alcaro、Francesco Ortuso

  DOI：10.1016/j.bmcl.2004.05.010

  日期：2004.7

  A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, displaying pIC(50) values of particular interest: 2a shows pIC(50) 7.76 and a selectivity index (pS.I.) 2.94 and 2b shows pIC(50) 7.72 and a pS.I. of 2.80. The coumarin-3-acyl chlorides 3a-e showed high pIC(50) values against both MAO-A and MAO-B isoforms, 3d being the highest against MAO-B with a pIC(50) value of 8.00. In order to rationalize the activity/selectivity results, molecular descriptors were generated. Further insight about enzyme-inhibitor interaction was obtained by docking experiments with the MAO-B isoform. (C) 2004 Elsevier Ltd. All rights reserved.