3-Oxo-3,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazine-4-carboxylic acid ethyl ester | 183740-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-Oxo-3,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazine-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-oxo-3,4-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2,6,11,13-pentaene-6-carboxylate
• CAS: 183740-18-3
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: ALNNKBQCCPDWOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Oxo-3,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazine-4-carboxylic acid ethyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 2-Carboxymethyl-3-oxo-3,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, Activity, and Molecular Modeling of a New Series of Tricyclic Pyridazinones as Selective Aldose Reductase Inhibitors

  摘要：

  Three new series of tricyclic pyridazinones have been synthesized and tested in vitro in order to assess (i) their ability to inhibit aldose reductase enzyme (ALR2) and (ii) their specificity toward the target enzyme with respect to other related oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. The inhibitory capability of the most effective compounds (IC50 values ranging from 6.44 to 12.6 mu M) appears to be associated with a rather significant specificity for ALR2. Molecular mechanics and molecular dynamic calculations performed on the ALR2-inhibitor complex give indications of specific interaction sites responsible for the binding, thus providing information for the design of new inhibitors with improved affinity for the enzyme.

  DOI：

  10.1021/jm960124f
• 作为产物：
  描述：

  1-苯并环庚酮 在 一水合肼 、 溶剂黄146 作用下， 反应 12.0h， 生成 3-Oxo-3,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, Activity, and Molecular Modeling of a New Series of Tricyclic Pyridazinones as Selective Aldose Reductase Inhibitors

  摘要：

  Three new series of tricyclic pyridazinones have been synthesized and tested in vitro in order to assess (i) their ability to inhibit aldose reductase enzyme (ALR2) and (ii) their specificity toward the target enzyme with respect to other related oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. The inhibitory capability of the most effective compounds (IC50 values ranging from 6.44 to 12.6 mu M) appears to be associated with a rather significant specificity for ALR2. Molecular mechanics and molecular dynamic calculations performed on the ALR2-inhibitor complex give indications of specific interaction sites responsible for the binding, thus providing information for the design of new inhibitors with improved affinity for the enzyme.

  DOI：

  10.1021/jm960124f

文献信息

• Synthesis, Activity, and Molecular Modeling of a New Series of Tricyclic Pyridazinones as Selective Aldose Reductase Inhibitors
  作者：Luca Costantino、Giulio Rastelli、Katia Vescovini、Giorgio Cignarella、Paola Vianello、Antonella Del Corso、Mario Cappiello、Umberto Mura、Daniela Barlocco

  DOI：10.1021/jm960124f

  日期：1996.1.1

  Three new series of tricyclic pyridazinones have been synthesized and tested in vitro in order to assess (i) their ability to inhibit aldose reductase enzyme (ALR2) and (ii) their specificity toward the target enzyme with respect to other related oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. The inhibitory capability of the most effective compounds (IC50 values ranging from 6.44 to 12.6 mu M) appears to be associated with a rather significant specificity for ALR2. Molecular mechanics and molecular dynamic calculations performed on the ALR2-inhibitor complex give indications of specific interaction sites responsible for the binding, thus providing information for the design of new inhibitors with improved affinity for the enzyme.