4-[3-(3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-2-oxo-propoxy]-benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[3-(3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-2-oxo-propoxy]-benzoic acid
• 英文别名: 4-[(3Z)-3-(3,3-dimethyl-1H-indol-2-ylidene)-2-oxopropoxy]benzoic acid
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: AUDFLSCTUPCODN-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 4-(2-methoxy-2-oxoethoxy)benzoic acid 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到4-[3-(3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-2-oxo-propoxy]-benzoic acid
  参考文献：
  名称：

  Non-steroidal anti-inflammatory agents. Part 23. Synthesis and Pharmacological Activity of Enaminones which inhibit both bovine cyclooxygenase and 5-lipoxygenase

  摘要：

  The synthesis and stereochemical characteristics of pyrrolidino-, isoquinolino- and indolo-enaminones 2-11 are reported. The inhibition of cyclooxygenase was determined in a bovine thrombocyte intact cell assay and that of 5-lipoxygenase using intact bovine polymorphonuclear leucocytes. Except compound 2c' which is a well-balanced dual inhibitor of both enzymes, all other enaminone derivatives are weak inhibitors of both cyclooxygenase and 5-lipoxygenase. Structure-activity relationships of the enaminones in relation to known anti-inflammatory drugs are discussed.

  DOI：

  10.1002/prac.19983400309