(5-Methoxy-1,3-dimethyl-4,7-dioxoindol-2-yl)methyl 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate | 1601465-93-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5-Methoxy-1,3-dimethyl-4,7-dioxoindol-2-yl)methyl 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate
• 英文别名: (5-methoxy-1,3-dimethyl-4,7-dioxoindol-2-yl)methyl 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate
• CAS: 1601465-93-3
• 化学式: C₃₆H₃₉NO₅
• 分子量: 565.709
• InChiKey: GVOJLTGZEMWKFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 5-methoxy-3-methyl-1H-indole-2-carboxylate 在 盐酸 、 tin 、 lithium aluminium tetrahydride 、 硝酸 、 三苯基膦 、 potassium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.17h， 生成 (5-Methoxy-1,3-dimethyl-4,7-dioxoindol-2-yl)methyl 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate
  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