methyl 5-methoxy-3-methyl-4-nitro-1H-indole-2-carboxylate | 1601465-92-2

• 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 5-methoxy-3-methyl-4-nitro-1H-indole-2-carboxylate
• CAS: 1601465-92-2
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: BUARTQIIJVYGAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-3-methyl-4-nitro-1H-indole-2-carboxylate 在 盐酸 、 tin 、 lithium aluminium tetrahydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-hydroxymethyl-5-methoxy-1,3-dimethylindole-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：

  2-乙基乙酰乙酸甲酯 在 盐酸 、 硝酸 、 sodium acetate 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.42h， 生成 methyl 5-methoxy-3-methyl-4-nitro-1H-indole-2-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

文献信息

• [EN] PHOSPHORAMIDE COMPOUNDS<br/>[FR] COMPOSES DE PHOSPHORAMIDE
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2001004130A1

  公开（公告）日：2001-01-18

  The invention provides a compound of formula (I): wherein R1, Ra, Rb, Rc, and Rd have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds or salts. The compounds are useful for treating cancer in animals.