[(19S)-19-ethyl-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate | 741283-04-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: [(19S)-19-ethyl-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate
• CAS: 741283-04-5
• 化学式: C₃₀H₃₂N₂O₉
• 分子量: 564.592
• InChiKey: RIEUVAUJXBBNDU-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(19S)-19-ethyl-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 2.0h， 以71%的产率得到
  参考文献：
  名称：

  Synthesis and biological evaluation of bis and monocarbonate prodrugs of 10-hydroxycamptothecins

  摘要：

  In an effort to improve the stability of labile lactone ring of camptothecins, the his and mono-alkyl carbonate prodrugs of 10-hydroxycamptothecins were synthesized and their chemical and enzymatical stability as well as antitumor activity were studied. The in vitro evaluation of the stability of these carbonates indicates that the 10,20-biscarbonates are firstly hydrolyzed to afford the stable 20-monocarbonates. And the 10-carbonates are not stable in human plasma, mouse plasma and pH 7.4 phosphate buffer, while the 20-carbonates are relatively stable in the three media and can be readily cleaved by porcine liver esterase. The overall toxicity of the tested carbonate against mice bearing S 180 sarcoma is much lower when compared with the parent compound, and the antitumor activity is maintained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.003
• 作为产物：
  描述：

  10-羟基喜树碱 、 氯甲酸异丁酯 以 二氯甲烷 为溶剂， 生成 [(19S)-19-ethyl-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate
  参考文献：
  名称：

  New Method for the Synthesis of 5‐Hydroxycamptothecin Derivatives

  摘要：

  An efficient hydroxylation at the 5-position of the C ring of camptothecins was accomplished with the complex of CuI and organic amines as catalyst in the presence of oxygen at room temperature in dimethyl formate (DMF). To be successfully hydroxylated. the insoluble camptothecin analogue was transformed to the corresponding 20 carbonates.

  DOI：

  10.1081/scc-200039356