(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-({4-[bis-(2-chloro-ethyl)-amino]-phenoxycarbonyl}-methyl-amino)-4-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester | 191352-31-5

• 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)-3,4,5-Triacetoxy-6-[2-({4-[bis-(2-chloro-ethyl)-amino]-phenoxycarbonyl}-methyl-amino)-4-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 191352-31-5
• 化学式: C₃₁H₃₅Cl₂N₃O₁₄
• 分子量: 744.537
• InChiKey: GORYCLDWGKMMTI-RKBVRRORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  199.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-({4-[bis-(2-chloro-ethyl)-amino]-phenoxycarbonyl}-methyl-amino)-4-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 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
• 作为产物：
  描述：

  2-(methylamino)-4-nitrophenol 在 盐酸 、 potassium carbonate 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-({4-[bis-(2-chloro-ethyl)-amino]-phenoxycarbonyl}-methyl-amino)-4-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  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