5-methoxy-4-(methoxymethoxy)-2-phenylindole-3-carbaldehyde | 164414-11-3

• 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: 5-methoxy-4-(methoxymethoxy)-2-phenylindole-3-carbaldehyde
• 英文别名: 5-methoxy-4-(methoxymethoxy)-2-phenyl-1H-indole-3-carbaldehyde
• CAS: 164414-11-3
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: ABDLYGTXIZYIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-4-(methoxymethoxy)-2-phenylindole-3-carbaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到5-methoxy-4-(methoxymethoxy)-3-methyl-2-phenylindole
  参考文献：
  名称：

  Hydroxyindole derivatives as inhibitors of IL-1 generation. I. Synthesis and pharmacological activities of (E)-3-(4-hydroxy-5-methoxyindole-7-yl)-2-methylpropenoic acid derivatives

  摘要：

  A series of (E)-3-(4-hydroxy-5-methoxyindole-7-yl)-2-methylpropenoic acids was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vivo system using the rat carboxymethyl cellulose-lipopolysaccharide (CMC-LPS) air-pouch model. Many compounds in this new series were found to be inhibitors of IL-1 generation. Structure-activity relationships indicated that a methyl substituent at the 1- and 3-positions on the indole ring are important for activity and that a 3,4,5-trimethoxy-substituted 2-phenyl group on the indole ring is suitable to give compounds exhibiting inhibition oral administration. Among the compounds evaluated, (E)-3-[1,3-dimethyl-4-hydroxy-5-methoxy-2-(3,4,5-trimethoxyphenyl)indole-7-yl]-2-methylpropenoic acid (15m), which inhibited IL-1 generation by human monocytes stimulated with various reagents such as LPS, opsonized zymosan and immune complexes, showed inhibitory activity in the rat CMC-LPS model after oral administration.

  DOI：

  10.1016/0223-5234(96)88224-9
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 5-methoxy-4-(methoxymethoxy)-2-phenylindole 在 三氯氧磷 作用下， 生成 5-methoxy-4-(methoxymethoxy)-2-phenylindole-3-carbaldehyde
  参考文献：
  名称：

  Hydroxyindole derivatives as inhibitors of IL-1 generation. I. Synthesis and pharmacological activities of (E)-3-(4-hydroxy-5-methoxyindole-7-yl)-2-methylpropenoic acid derivatives

  摘要：

  A series of (E)-3-(4-hydroxy-5-methoxyindole-7-yl)-2-methylpropenoic acids was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vivo system using the rat carboxymethyl cellulose-lipopolysaccharide (CMC-LPS) air-pouch model. Many compounds in this new series were found to be inhibitors of IL-1 generation. Structure-activity relationships indicated that a methyl substituent at the 1- and 3-positions on the indole ring are important for activity and that a 3,4,5-trimethoxy-substituted 2-phenyl group on the indole ring is suitable to give compounds exhibiting inhibition oral administration. Among the compounds evaluated, (E)-3-[1,3-dimethyl-4-hydroxy-5-methoxy-2-(3,4,5-trimethoxyphenyl)indole-7-yl]-2-methylpropenoic acid (15m), which inhibited IL-1 generation by human monocytes stimulated with various reagents such as LPS, opsonized zymosan and immune complexes, showed inhibitory activity in the rat CMC-LPS model after oral administration.

  DOI：

  10.1016/0223-5234(96)88224-9