(2S,3S,4S,5R,6S)-6-[4-[[(6aS)-3-[5-[[(6aS)-2-methoxy-6,11-dioxo-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-6-hydroxy-2-methoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl]oxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid | 1047976-75-9

• 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-[4-[[(6aS)-3-[5-[[(6aS)-2-methoxy-6,11-dioxo-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-6-hydroxy-2-methoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl]oxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1047976-75-9
• 化学式: C₄₅H₅₁N₅O₁₉
• 分子量: 965.922
• InChiKey: ASYIHHCJVFNXOB-VAOQNCLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  69
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  319
• 氢给体数：
  6
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-[4-[[(6aS)-3-[5-[[(6aS)-2-methoxy-6,11-dioxo-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-6-hydroxy-2-methoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl]oxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid 在 E. coli β-glucuronidase 作用下， 生成 NSC 718813
  参考文献：
  名称：

  Pyrrolo[2,1-c][1,4]benzodiazepine-β-glucuronide prodrugs with a potential for selective therapy of solid tumors by PMT and ADEPT strategies

  摘要：

  Pyrrolo[2,1-c][1,4]benzodiazepine-beta-glucuronide prodrugs 15a-b, with a potential for selective therapy of solid tumors by PMT and ADEPT have been designed, synthesized and evaluated for selective cytotoxicity in the presence of the enzyme beta-glucuronidase. The prodrugs have been found to possess reduced cytotoxicity compared to the parent moieties, and are excellent substrates for the enzyme, exhibiting cytotoxicity selectively in the presence of the enzyme. Enhanced water solubility and improved stability are the other important outcomes upon modifying these molecules as their prodrugs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.038
• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以76%的产率得到(2S,3S,4S,5R,6S)-6-[4-[[(6aS)-3-[5-[[(6aS)-2-methoxy-6,11-dioxo-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-6-hydroxy-2-methoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl]oxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Pyrrolo[2,1-c][1,4]benzodiazepine-β-glucuronide prodrugs with a potential for selective therapy of solid tumors by PMT and ADEPT strategies

  摘要：

  Pyrrolo[2,1-c][1,4]benzodiazepine-beta-glucuronide prodrugs 15a-b, with a potential for selective therapy of solid tumors by PMT and ADEPT have been designed, synthesized and evaluated for selective cytotoxicity in the presence of the enzyme beta-glucuronidase. The prodrugs have been found to possess reduced cytotoxicity compared to the parent moieties, and are excellent substrates for the enzyme, exhibiting cytotoxicity selectively in the presence of the enzyme. Enhanced water solubility and improved stability are the other important outcomes upon modifying these molecules as their prodrugs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.038

文献信息

• Pyrrolo[2,1-c][1,4]benzodiazepine-β-glucuronide prodrugs with a potential for selective therapy of solid tumors by PMT and ADEPT strategies
  作者：Ahmed Kamal、Venkatesh Tekumalla、P. Raju、V.G.M. Naidu、Prakash V. Diwan、Ramakrishna Sistla

  DOI：10.1016/j.bmcl.2008.05.038

  日期：2008.7

  Pyrrolo[2,1-c][1,4]benzodiazepine-beta-glucuronide prodrugs 15a-b, with a potential for selective therapy of solid tumors by PMT and ADEPT have been designed, synthesized and evaluated for selective cytotoxicity in the presence of the enzyme beta-glucuronidase. The prodrugs have been found to possess reduced cytotoxicity compared to the parent moieties, and are excellent substrates for the enzyme, exhibiting cytotoxicity selectively in the presence of the enzyme. Enhanced water solubility and improved stability are the other important outcomes upon modifying these molecules as their prodrugs. (C) 2008 Elsevier Ltd. All rights reserved.