4-(6,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-ylamino)-benzoic acid | 100448-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(6,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-ylamino)-benzoic acid
• 英文别名: 4-[(6,7-dimethoxy-4-oxo-3H-quinazolin-2-yl)amino]benzoic acid
• CAS: 100448-62-2
• 化学式: C₁₇H₁₅N₃O₅
• 分子量: 341.323
• InChiKey: LNNQNKVIWYUPNE-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  570.0±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二氯-6,7-二甲氧基喹唑啉 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(6,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-ylamino)-benzoic acid
  参考文献：
  名称：

  Design and synthesis of 2-(arylamino)-4(3H)-quinazolinones as novel inhibitors of rat lens aldose reductase

  摘要：

  A number of 2-(arylamino)-4(3H)-quinazolinones (2a-i) that possess several of the pharmacophore moieties necessary for binding to the inhibitor site of the enzyme aldose reductase were synthesized and tested for their ability to inhibit crude aldose reductase obtained from rat lens. Only those quinazolinones that possess an acidic moiety on the 2-(arylamino) substituent were found to display significant inhibitory activity. Of these, the most potent compound is the 4'-CO2H derivative (2i) with an IC50 of 34 microM, while the least potent is the 4'-OH derivative (2c) with an IC50 of 75 microM. All of the 2-(arylamino)-4(3H)-quinazolinones tested are less potent than other known inhibitors of aldose reductase, such as alrestatin and sorbinil, indicating that the pharmacophore moieties present in these compounds may not be positioned optimally relative to one another for maximal interaction with the enzyme.

  DOI：

  10.1021/jm00155a007

文献信息

• DERUITER, J.;BRUBAKER, A. N.;MILLEN, J.;RILEY, T. N., J. MED. CHEM., 1986, 29, N 5, 627-629
  作者：DERUITER, J.、BRUBAKER, A. N.、MILLEN, J.、RILEY, T. N.

  DOI：——

  日期：——
• Design and synthesis of 2-(arylamino)-4(3H)-quinazolinones as novel inhibitors of rat lens aldose reductase
  作者：Jack DeRuiter、Abram N. Brubaker、Jane Millen、Thomas N. Riley

  DOI：10.1021/jm00155a007

  日期：1986.5

  A number of 2-(arylamino)-4(3H)-quinazolinones (2a-i) that possess several of the pharmacophore moieties necessary for binding to the inhibitor site of the enzyme aldose reductase were synthesized and tested for their ability to inhibit crude aldose reductase obtained from rat lens. Only those quinazolinones that possess an acidic moiety on the 2-(arylamino) substituent were found to display significant inhibitory activity. Of these, the most potent compound is the 4'-CO2H derivative (2i) with an IC50 of 34 microM, while the least potent is the 4'-OH derivative (2c) with an IC50 of 75 microM. All of the 2-(arylamino)-4(3H)-quinazolinones tested are less potent than other known inhibitors of aldose reductase, such as alrestatin and sorbinil, indicating that the pharmacophore moieties present in these compounds may not be positioned optimally relative to one another for maximal interaction with the enzyme.