methyl 2-(3-hydroxybenzamido)-4,5-dimethoxybenzoate | 1400173-76-3

• 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: methyl 2-(3-hydroxybenzamido)-4,5-dimethoxybenzoate
• CAS: 1400173-76-3
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: AAHIYYQUXOMHBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-hydroxybenzamido)-4,5-dimethoxybenzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以74%的产率得到2-(3-hydroxybenzamido)-4,5-dimethoxybenzoic acid
  参考文献：
  名称：

  N-Benzoyl anthranilic acid derivatives as selective inhibitors of aldo–keto reductase AKR1C3

  摘要：

  Human aldo-keto reductases AKR1C1-AKR1C3 are involved in the biosynthesis and inactivation of steroid hormones and prostaglandins and thus represent attractive targets for the development of new drugs. We synthesized a series of N-benzoyl anthranilic acid derivatives and tested their inhibitory activity on AKR1C enzymes. Our data show that these derivatives inhibit AKR1C1-AKR1C3 isoforms with low micromolar potency. In addition, five selective inhibitors of AKR1C3 were identified. The most promising inhibitors were compounds 10 and 13, with IC50 values of 0.31 mu M and 0.35 mu M for AKR1C3, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.062
• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸甲酯 、 间羟基苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 以71%的产率得到methyl 2-(3-hydroxybenzamido)-4,5-dimethoxybenzoate
  参考文献：
  名称：

  N-Benzoyl anthranilic acid derivatives as selective inhibitors of aldo–keto reductase AKR1C3

  摘要：

  Human aldo-keto reductases AKR1C1-AKR1C3 are involved in the biosynthesis and inactivation of steroid hormones and prostaglandins and thus represent attractive targets for the development of new drugs. We synthesized a series of N-benzoyl anthranilic acid derivatives and tested their inhibitory activity on AKR1C enzymes. Our data show that these derivatives inhibit AKR1C1-AKR1C3 isoforms with low micromolar potency. In addition, five selective inhibitors of AKR1C3 were identified. The most promising inhibitors were compounds 10 and 13, with IC50 values of 0.31 mu M and 0.35 mu M for AKR1C3, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.062