5-carboxymethyl-5,6-dihydro-11H-dibenzoazepin-6,11-dione | 119656-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 5-carboxymethyl-5,6-dihydro-11H-dibenzoazepin-6,11-dione
• 英文别名: (6,11-Dioxo-6,11-dihydro-dibenzo[b,e]azepin-5-yl)-acetic acid；2-(6,11-dioxobenzo[c][1]benzazepin-5-yl)acetic acid
• CAS: 119656-56-3
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: XDEOJTNMLAAQPA-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  551.6±50.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-carboxymethyl-5,6-dihydro-11H-dibenzoazepin-6,11-dione 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 2-(6,11-dioxobenzo[c][1]benzazepin-5-yl)-N,N-diethylacetamide
  参考文献：
  名称：

  New [dibenzo(b,e)azepin-5-yl]-acetamides with anti-convulsant activity

  摘要：

  DOI：

  10.1016/0223-5234(93)90132-x
• 作为产物：
  描述：

  5H-二苯并[b,e]氮杂卓-6,11-二酮 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 5-carboxymethyl-5,6-dihydro-11H-dibenzoazepin-6,11-dione
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017

文献信息

• J. MED. CHEM., 32,(1989) N, C. 1033-1038
  作者：

  DOI：——

  日期：——
• Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety
  作者：Jack DeRuiter、Blake E. Swearingen、Vinay Wandrekar、Charles A. Mayfield

  DOI：10.1021/jm00125a017

  日期：1989.5

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.
• New [dibenzo(b,e)azepin-5-yl]-acetamides with anti-convulsant activity
  作者：G Viti、D Giannotti、M Altamura、R Ricci、G Volterra、A Lecci、F Borsini、V Pestellini

  DOI：10.1016/0223-5234(93)90132-x

  日期：1993.1