4-benzyloxy-5-methoxy-2-methyl-3-nitrobenzoic acid | 176963-39-6

• 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: 4-benzyloxy-5-methoxy-2-methyl-3-nitrobenzoic acid
• 英文别名: 5-Methoxy-2-methyl-3-nitro-4-phenylmethoxybenzoic acid
• CAS: 176963-39-6
• 化学式: C₁₆H₁₅NO₆
• 分子量: 317.298
• InChiKey: PVNHEFWJUPBIMV-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±50.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-5-methoxy-2-methyl-3-nitrobenzoic acid 在 palladium on activated charcoal 四氢吡咯 、 氢气 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 1-乙基-7-羟基-6-甲氧基吲哚-4-羧酸甲酯
  参考文献：
  名称：

  Hydroxyindole derivatives as inhibitors of IL-1 generation. II. Synthesis and pharmacological activities of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives

  摘要：

  A series of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vitro system using exudate cells from the rat carboxymethyl cellulose (CMC) induced air-pouch model. All the compounds in this new series were found to be inhibitors of IL-1 generation. In particular, the methoxy-substituted 2-phenyl compounds 28d-f were the most potent inhibitors of IL-1 generation (eg, 28d: IC50 = 0.8 mu M). The compounds in this series also inhibited IL-1 alpha and IL-1 beta generations in an in vitro system using human monocytes stimulated with LPS (eg, 28b: IC50 = 1.4 mu M (IL-1 alpha) and 0.9 mu M (IL-1 beta)).

  DOI：

  10.1016/0223-5234(96)89134-3
• 作为产物：
  描述：

  4-羟基-5-甲氧基-2-甲基苯甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate 、 硝酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 2.75h， 生成 4-benzyloxy-5-methoxy-2-methyl-3-nitrobenzoic acid
  参考文献：
  名称：

  Hydroxyindole derivatives as inhibitors of IL-1 generation. II. Synthesis and pharmacological activities of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives

  摘要：

  A series of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vitro system using exudate cells from the rat carboxymethyl cellulose (CMC) induced air-pouch model. All the compounds in this new series were found to be inhibitors of IL-1 generation. In particular, the methoxy-substituted 2-phenyl compounds 28d-f were the most potent inhibitors of IL-1 generation (eg, 28d: IC50 = 0.8 mu M). The compounds in this series also inhibited IL-1 alpha and IL-1 beta generations in an in vitro system using human monocytes stimulated with LPS (eg, 28b: IC50 = 1.4 mu M (IL-1 alpha) and 0.9 mu M (IL-1 beta)).

  DOI：

  10.1016/0223-5234(96)89134-3