4-methoxy-3-(methoxymethoxy)-2-methylaniline | 164414-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-3-(methoxymethoxy)-2-methylaniline
• CAS: 164414-07-7
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: XSXZYFNCKDKHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间甲氧基苯甲酰氯 、 4-methoxy-3-(methoxymethoxy)-2-methylaniline 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 3-methoxy-N-[4-methoxy-3-(methoxymethoxy)-2-methylphenyl]benzamide
  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：

  2-(methoxymethoxy)-3-methyl-4-nitroanisole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以99%的产率得到4-methoxy-3-(methoxymethoxy)-2-methylaniline
  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

文献信息

• 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
  作者：M Tanaka、T Kaneko、H Akamatsu、M Okita、K Chiba、H Obaishi、H Sakurai、I Yamatsu

  DOI：10.1016/0223-5234(96)88224-9

  日期：1995.1

  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.