2-Ethoxycarbonylmethyl-6-(4-isopropyl-phenyl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester | 158977-84-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Ethoxycarbonylmethyl-6-(4-isopropyl-phenyl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-(2-ethoxy-2-oxoethyl)-3-oxo-6-(4-propan-2-ylphenyl)pyridazine-4-carboxylate
• CAS: 158977-84-5
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: BQPNYXFLDTZHDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Ethoxycarbonylmethyl-6-(4-isopropyl-phenyl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到2-Carboxymethyl-6-(4-isopropyl-phenyl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of pyridazine acetic acid derivatives possessing aldose reductase inhibitory activity and antioxidant properties

  摘要：

  N-Acetic acid derivatives of 4-carboxy-6-arylpyridazin-3-ones were synthesized for the dual purpose of inhibiting aldose reductase and exhibiting antioxidant properties. All the prepared compounds showed a significant in vitro aldose reductase inhibitory effect (10(-5) M less than or equal to IC50 less than or equal to 10(-4) M). The spatial configuration of the most active derivative 4f (4-i-PrC6H4 at C-6, IC50 = 0 95 x 10(-5) M) was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system. The antioxidant action of 4a-f was also studied in vitro. Compound 4c (4-ClC6H4 at C-6, IC50 = 1.56 x 10(-3) M) was the most effective at scavenging the superoxide anion whereas compound 4a (C6H5 at C-6, IC50 = 1.28 x 10(-3) M) was the most active at inhibiting lipid peroxidation. In addition, biological activities (log 1/IC50) for most of the data sets could be correlated directly to lipophilic, electronic and steric parameters.

  DOI：

  10.1016/0223-5234(94)90074-4
• 作为产物：
  描述：

  2-Hydroxy-2-[2-(4-isopropyl-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester 在 盐酸肼 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 44.0h， 生成 2-Ethoxycarbonylmethyl-6-(4-isopropyl-phenyl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of pyridazine acetic acid derivatives possessing aldose reductase inhibitory activity and antioxidant properties

  摘要：

  N-Acetic acid derivatives of 4-carboxy-6-arylpyridazin-3-ones were synthesized for the dual purpose of inhibiting aldose reductase and exhibiting antioxidant properties. All the prepared compounds showed a significant in vitro aldose reductase inhibitory effect (10(-5) M less than or equal to IC50 less than or equal to 10(-4) M). The spatial configuration of the most active derivative 4f (4-i-PrC6H4 at C-6, IC50 = 0 95 x 10(-5) M) was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system. The antioxidant action of 4a-f was also studied in vitro. Compound 4c (4-ClC6H4 at C-6, IC50 = 1.56 x 10(-3) M) was the most effective at scavenging the superoxide anion whereas compound 4a (C6H5 at C-6, IC50 = 1.28 x 10(-3) M) was the most active at inhibiting lipid peroxidation. In addition, biological activities (log 1/IC50) for most of the data sets could be correlated directly to lipophilic, electronic and steric parameters.

  DOI：

  10.1016/0223-5234(94)90074-4

文献信息

• Synthesis of pyridazine acetic acid derivatives possessing aldose reductase inhibitory activity and antioxidant properties
  作者：P Coudert、E Albuisson、JY Boire、E Duroux、P Bastide、J Couquelet

  DOI：10.1016/0223-5234(94)90074-4

  日期：1994.1

  N-Acetic acid derivatives of 4-carboxy-6-arylpyridazin-3-ones were synthesized for the dual purpose of inhibiting aldose reductase and exhibiting antioxidant properties. All the prepared compounds showed a significant in vitro aldose reductase inhibitory effect (10(-5) M less than or equal to IC50 less than or equal to 10(-4) M). The spatial configuration of the most active derivative 4f (4-i-PrC6H4 at C-6, IC50 = 0 95 x 10(-5) M) was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system. The antioxidant action of 4a-f was also studied in vitro. Compound 4c (4-ClC6H4 at C-6, IC50 = 1.56 x 10(-3) M) was the most effective at scavenging the superoxide anion whereas compound 4a (C6H5 at C-6, IC50 = 1.28 x 10(-3) M) was the most active at inhibiting lipid peroxidation. In addition, biological activities (log 1/IC50) for most of the data sets could be correlated directly to lipophilic, electronic and steric parameters.