(2S,3S,4S,5R,6S)-6-(4-{[Bis-(2-chloro-ethyl)-carbamoyloxy]-methyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 302937-44-6

• 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-(4-{[Bis-(2-chloro-ethyl)-carbamoyloxy]-methyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-6-[4-[bis(2-chloroethyl)carbamoyloxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 302937-44-6
• 化学式: C₁₉H₂₄Cl₂N₂O₁₁
• 分子量: 527.312
• InChiKey: PJXNLERSPUQTOV-RNGZQALNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-(4-{[Bis-(2-chloro-ethyl)-carbamoyloxy]-methyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 barium dihydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以36%的产率得到(2S,3S,4S,5R,6S)-6-(4-{[Bis-(2-chloro-ethyl)-carbamoyloxy]-methyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and cytotoxic activity of a glucuronylated prodrug of nornitrogen mustard

  摘要：

  A new glucuronlylated prodrug of nornitrogen mustard, incorporating the same spacer group as the doxorubicin prodrug HMR 1826, has been prepared. Upon exposure to E. coli beta-glucuronidase, fast hydrolysis occurs but a lower cytotoxicity against LoVo cancer cells is observed compared to the nornitrogen mustard alone. This is explained by cyclization of the intermediate carbamic acid to the inactive chloroethyl oxazolidinone. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00353-x
• 作为产物：
  描述：

  (2S,3S,5R,6S)-2-(methoxycarbonyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (2S,3S,4S,5R,6S)-6-(4-{[Bis-(2-chloro-ethyl)-carbamoyloxy]-methyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and cytotoxic activity of a glucuronylated prodrug of nornitrogen mustard

  摘要：

  A new glucuronlylated prodrug of nornitrogen mustard, incorporating the same spacer group as the doxorubicin prodrug HMR 1826, has been prepared. Upon exposure to E. coli beta-glucuronidase, fast hydrolysis occurs but a lower cytotoxicity against LoVo cancer cells is observed compared to the nornitrogen mustard alone. This is explained by cyclization of the intermediate carbamic acid to the inactive chloroethyl oxazolidinone. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00353-x

文献信息

• Synthesis and cytotoxic activity of a glucuronylated prodrug of nornitrogen mustard
  作者：Sébastien Papot、Damien Combaud、Klaus Bosslet、Manfred Gerken、Jorg Czech、Jean-Pierre Gesson

  DOI：10.1016/s0960-894x(00)00353-x

  日期：2000.8

  A new glucuronlylated prodrug of nornitrogen mustard, incorporating the same spacer group as the doxorubicin prodrug HMR 1826, has been prepared. Upon exposure to E. coli beta-glucuronidase, fast hydrolysis occurs but a lower cytotoxicity against LoVo cancer cells is observed compared to the nornitrogen mustard alone. This is explained by cyclization of the intermediate carbamic acid to the inactive chloroethyl oxazolidinone. (C) 2000 Elsevier Science Ltd. All rights reserved.