2-(2-acetoxybenzoyloxy)propen-1-yl-5-methoxy-1-methylindole-4,7-dione | 192820-71-6

• 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: 2-(2-acetoxybenzoyloxy)propen-1-yl-5-methoxy-1-methylindole-4,7-dione
• 英文别名: 3-(2-Acetoxybenzoyloxy) methyl-1,2-dimethyl-5-methoxyindole-4,7-dione；3-(2-Acetoxybenzoyloxy)-methyl-1,2-dimethyl-5-methoxyindole-4,7-dione；(5-Methoxy-1,2-dimethyl-4,7-dioxoindol-3-yl)methyl 2-acetyloxybenzoate
• CAS: 192820-71-6
• 化学式: C₂₁H₁₉NO₇
• 分子量: 397.384
• InChiKey: PTABCNLLFORKRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-acetoxybenzoyloxy)propen-1-yl-5-methoxy-1-methylindole-4,7-dione 在 phosphate buffer at pH 7.4 、 异丙醇 、 一氧化二氮 作用下， 以 水 为溶剂， 生成 2-Acetoxy-benzoic acid 4,7-dihydroxy-5-methoxy-1,2-dimethyl-1H-indol-3-ylmethyl ester
  参考文献：
  名称：

  Prodrugs for targeting hypoxic tissues: Regiospecific elimination of aspirin from reduced indolequinones

  摘要：

  A series of regioisomeric derivatives of a 1-methylindole-4,7-dione were synthesised, substituted with a 2-acetoxybenzoate leaving group linked through the (indol-2-yl)methyl or (indol-3-yl)methyl (or propenyl) positions. Reductive elimination of the leaving group occurred from the (indol-3-yl)methyl derivatives but not the 2-substituted regioisomers, indicating that only the C-3 position may be utilised in bioreductively-activated drug delivery, which was demonstrated with an aspirin prodrug. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00695-7
• 作为产物：
  描述：

  2-acetylsalicylic acid chloride 、 3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione 在 吡啶 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2-(2-acetoxybenzoyloxy)propen-1-yl-5-methoxy-1-methylindole-4,7-dione
  参考文献：
  名称：

  BIOREDUCTIVE CONJUGATES FOR DRUG TARGETING

  摘要：

  公开号：

  EP0988057B1

文献信息

• ENHANCED PRODRUG ACTIVATION
  申请人：Oxford Biomedica (UK) Limited

  公开号：EP1068338A2

  公开（公告）日：2001-01-17
• US7829555B1
  申请人：——

  公开号：US7829555B1

  公开（公告）日：2010-11-09
• [EN] ENHANCED PRODRUG ACTIVATION<br/>[FR] ACTIVATION AMELIOREE DE PROMEDICAMENTS
  申请人：——

  公开号：WO1999045127A2

  公开（公告）日：1999-09-10

  [EN] A prodrug activating agent comprising: a) a localisation domain and b) a prodrug activation domain for activating a prodrug in a target cell.
  [FR] L'invention concerne un agent d'activation de promédicaments renfermant: a) un domaine de localisation et b) un domaine d'activation de promédicaments destiné à activer un promédicament dans une cellule cible.
• Prodrugs for targeting hypoxic tissues: Regiospecific elimination of aspirin from reduced indolequinones
  作者：M Jaffar、S.A Everett、M.A Naylor、S.G Moore、S Ulhaq、K.B Patel、M.R.L Stratford、J Nolan、P Wardman、I.J Stratford

  DOI：10.1016/s0960-894x(98)00695-7

  日期：1999.1

  A series of regioisomeric derivatives of a 1-methylindole-4,7-dione were synthesised, substituted with a 2-acetoxybenzoate leaving group linked through the (indol-2-yl)methyl or (indol-3-yl)methyl (or propenyl) positions. Reductive elimination of the leaving group occurred from the (indol-3-yl)methyl derivatives but not the 2-substituted regioisomers, indicating that only the C-3 position may be utilised in bioreductively-activated drug delivery, which was demonstrated with an aspirin prodrug. (C) 1998 Elsevier Science Ltd. All rights reserved.
• BIOREDUCTIVE CONJUGATES FOR DRUG TARGETING
  申请人：THE VICTORIA UNIVERSITY OF MANCHESTER

  公开号：EP0988057B1

  公开（公告）日：2003-08-27