(2S,3S,4S,5R,6S)-6-[2-[[4-[bis(2-chloroethyl)amino]phenoxy]carbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid | 191352-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-6-[2-[[4-[bis(2-chloroethyl)amino]phenoxy]carbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 191352-27-9
• 化学式: C₂₄H₂₇Cl₂N₃O₁₁
• 分子量: 604.398
• InChiKey: VPEYCUWENYIEBF-KHYDEXNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-[2-[[4-[bis(2-chloroethyl)amino]phenoxy]carbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid 生成 3-甲基-5-硝基-1,3-苯并恶唑-2-酮 、 N,N-双(2-氯乙基)-4-羟基苯胺
  参考文献：
  名称：

  Glucuronide prodrugs of hydroxy compounds for antibody directed enzyme prodrug therapy (ADEPT) : A phenol nitrogen mustard carbamate

  摘要：

  A prodrug consisting of a beta-D-glucuronic acid linked to a self-immolative spacer (a N-(orthohydroxyphenyl)-N-methylcarbamate) and a phenolic nitrogen mustard was synthesised. As this prodrug was easily cleaved by a beta-glucuronidase enzyme and displayed low cytotoxicity, it must be considered as appropriate for an ADEPT approach. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00157-1
• 作为产物：
  描述：

  4-[双(2-羟乙基)氨基]苯酚 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 氢气 、 sodium methylate 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 丙酮 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-[2-[[4-[bis(2-chloroethyl)amino]phenoxy]carbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Glucuronide prodrugs of hydroxy compounds for antibody directed enzyme prodrug therapy (ADEPT) : A phenol nitrogen mustard carbamate

  摘要：

  A prodrug consisting of a beta-D-glucuronic acid linked to a self-immolative spacer (a N-(orthohydroxyphenyl)-N-methylcarbamate) and a phenolic nitrogen mustard was synthesised. As this prodrug was easily cleaved by a beta-glucuronidase enzyme and displayed low cytotoxicity, it must be considered as appropriate for an ADEPT approach. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00157-1