2-hydroxy-2-(1-oxoindan-2-yl)malonic acid diethyl ester | 183740-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-hydroxy-2-(1-oxoindan-2-yl)malonic acid diethyl ester
• 英文别名: Diethyl 2-hydroxy-2-(3-oxo-1,2-dihydroinden-2-yl)propanedioate
• CAS: 183740-06-9
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: OTQQSTUGEMBGOU-UHFFFAOYSA-N

物化性质

• 沸点：
  440.5±30.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-(1-oxoindan-2-yl)malonic acid diethyl ester 在 盐酸 、 sodium hydroxide 、 盐酸肼 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 3-Oxo-3,5-dihydro-2H-indeno[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-茚酮 、 酮基丙二酸二乙酯 以82%的产率得到2-hydroxy-2-(1-oxoindan-2-yl)malonic acid diethyl 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 and biological evaluation of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines as new ligands of central and peripheral benzodiazepine receptors
  作者：Francesco Campagna、Fausta Palluotto、Maria Paola Mascia、Elisabetta Maciocco、Carla Marra、Angelo Carotti、Antonio Carrieri

  DOI：10.1016/s0014-827x(02)00017-4

  日期：2003.2

  A large number of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines were synthesised and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Relatively good PBR binding affinities were found for ligands belonging to the 3-arylmethyloxy-pyridazinoindole series, whereas only 2-aryl-indenopyridazines 7a, 8a and 10a display a weak binding affinity for CBR. To find out the main structural determinants affecting PBR affinity, a molecular modelling study based on the comparative analysis of the three-dimensional properties of four properly selected derivatives 24a, 3b, 18a and 10d, with those of highly active and selective PBR ligands, taken as reference, was performed.
• 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.