1-(t-butyloxycarbonyl)-3,3-di(methoxycarbonyl)-6-nitroindoline | 185433-51-6

• 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: 1-(t-butyloxycarbonyl)-3,3-di(methoxycarbonyl)-6-nitroindoline
• 英文别名: 1-O-tert-butyl 3-O,3-O'-dimethyl 6-nitro-2H-indole-1,3,3-tricarboxylate
• CAS: 185433-51-6
• 化学式: C₁₇H₂₀N₂O₈
• 分子量: 380.354
• InChiKey: PTCFVKMMGMZPRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(t-butyloxycarbonyl)-3,3-di(methoxycarbonyl)-6-nitroindoline 在 sodium methylate 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline
  参考文献：
  名称：

  A novel nitro-substituted seco-CI: Application as a reductively activated adept prodrug

  摘要：

  An alternative synthesis of seco-CI alkylating agents bearing a nitrogen substituent at C-6 is reported. The nitro compound 3 prepared by this route exhibits a 400-fold increase in cytotoxicity against UV4 cells in the presence of a nitroreductase enzyme from Escherichia coli B, suggesting it as a potential prodrug for use in antibody-directed enzyme prodrug therapy. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00508-2
• 作为产物：
  描述：

  3,3-bis(methoxycarbonyl)-6-nitroindolin-2-one 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 作用下， 生成 1-(t-butyloxycarbonyl)-3,3-di(methoxycarbonyl)-6-nitroindoline
  参考文献：
  名称：

  A novel nitro-substituted seco-CI: Application as a reductively activated adept prodrug

  摘要：

  An alternative synthesis of seco-CI alkylating agents bearing a nitrogen substituent at C-6 is reported. The nitro compound 3 prepared by this route exhibits a 400-fold increase in cytotoxicity against UV4 cells in the presence of a nitroreductase enzyme from Escherichia coli B, suggesting it as a potential prodrug for use in antibody-directed enzyme prodrug therapy. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00508-2

文献信息

• Cyclopropylindoles and their seco precursors, and their use as prodrugs
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05985909A1

  公开（公告）日：1999-11-16

  The present invention provides compounds of formula (I) and (II) which may be used as anticancer drugs.

  本发明提供了化合物(I)和(II)的公式，可用作抗癌药物。
• A novel nitro-substituted seco-CI: Application as a reductively activated adept prodrug
  作者：M. Tercel、W.A. Denny、W.R. Wilson

  DOI：10.1016/s0960-894x(96)00508-2

  日期：1996.11

  An alternative synthesis of seco-CI alkylating agents bearing a nitrogen substituent at C-6 is reported. The nitro compound 3 prepared by this route exhibits a 400-fold increase in cytotoxicity against UV4 cells in the presence of a nitroreductase enzyme from Escherichia coli B, suggesting it as a potential prodrug for use in antibody-directed enzyme prodrug therapy. Copyright (C) 1996 Elsevier Science Ltd
• US5985909A
  申请人：——

  公开号：US5985909A

  公开（公告）日：1999-11-16
• [EN] CYCLOPROPYLINDOLES AND THEIR SECO PRECURSORS, AND THEIR USE AS PRODRUGS<br/>[FR] CYCLOPROPYLINDOLES ET LEURS PRECURSEURS SECONDAIRES, ET UTILISATION DE CES COMPOSES EN TANT QUE PRECURSEURS DE MEDICAMENTS
  申请人：AUCKLAND DIVISION CANCER SOCIETY OF NEW ZEALAND INC.

  公开号：WO1997007097A1

  公开（公告）日：1997-02-27

  (EN) The present invention provides compounds of formula (I) and (II) which may be used as anticancer drugs.(FR) La présente invention se rapporte à des composés représentés par la formule (I) et la formule (II) qui peuvent s'avérer utiles en tant que médicaments anticancéreux.
• Tercel, Moana; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 509 - 519
  作者：Tercel, Moana、Denny, William A.

  DOI：——

  日期：——