<2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenyl>glyoxylic acid | 127792-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenyl>glyoxylic acid
• 英文别名: 2-[2-(2,6-dichloro-4-methoxyanilino)-5-methoxyphenyl]-2-oxoacetic acid
• CAS: 127792-39-6
• 化学式: C₁₆H₁₃Cl₂NO₅
• 分子量: 370.189
• InChiKey: MNOLHDOTVNZRDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  <2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenyl>glyoxylic acid 在 氢氧化钾 、 sodium hydroxide 、 sodium methylate 、 吡啶盐酸盐 、 一水合肼 作用下， 以 乙二醇甲醚 、 正丁醇 为溶剂， 反应 28.0h， 生成 (2-(2,6-二氯-4-羟基苯胺基)-5-羟基苯基)乙酸
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008
• 作为产物：
  描述：

  1,3-dihydro-N-[(2,6-dichloro-4-methoxy)phenyl]-5-methoxy-2H-indole-2,3-dione 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以87.3%的产率得到<2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenyl>glyoxylic acid
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008

文献信息

• MOSER, PETER;SALLMANN, ALFRED;WIESENBERG, IRMGARD, J. MED. CHEM. , 33,(1990) N, C. 2358-2368
  作者：MOSER, PETER、SALLMANN, ALFRED、WIESENBERG, IRMGARD

  DOI：——

  日期：——