methyl 4-amino-5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate | 1601465-85-3

• 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: methyl 4-amino-5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate
• CAS: 1601465-85-3
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: PKTGQNYEYBWZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以59%的产率得到3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
  参考文献：
  名称：

  Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)

  摘要：

  Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designed a prodrug strategy based on the enzyme NAD( P) H/quinone oxidoreductase (NQO1) that is elevated in neurodegenerative diseases. A series of indolequinones (known substrates of NQO1) was synthesized and coupled to bexarotene. Bexarotene-3(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione ester 7a was cleaved best by NQO1. The prodrugs are not cleaved by esterase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.003
• 作为产物：
  描述：

  3-methylaminobut-2-enoic acid methyl ester 在 盐酸 、 tin 、 硝酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 硝基甲烷 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 30.0h， 生成 methyl 4-amino-5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)

  摘要：

  Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designed a prodrug strategy based on the enzyme NAD( P) H/quinone oxidoreductase (NQO1) that is elevated in neurodegenerative diseases. A series of indolequinones (known substrates of NQO1) was synthesized and coupled to bexarotene. Bexarotene-3(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione ester 7a was cleaved best by NQO1. The prodrugs are not cleaved by esterase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.003