托尼依托泊苷 | 433304-61-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 中文名称: 托尼依托泊苷
• 英文名称: 4'-(2'',3''-isopropolideneglyceryl carbonoxy)-etoposide
• 英文别名: etoposide toniribate；CAP-7.1；Etoposide Toniribate；[4-[(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] (2,2-dimethyl-1,3-dioxolan-4-yl)methyl carbonate
• CAS: 433304-61-1
• 化学式: C₃₆H₄₂O₁₇
• 分子量: 746.719
• InChiKey: FCWSQAKOPTZCOD-SQYSSJHTSA-N

物化性质

• 沸点：
  883.3±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  53
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  托尼依托泊苷 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85.5%的产率得到4'-(2'',3''-dihydroxypropyl carbonoxy)-etoposide
  参考文献：
  名称：

  Synthesis, Hydrolytic Activation and Cytotoxicity of Etoposide Prodrugs

  摘要：

  Two 4'-propylcarbonoxy derivatives (2,3) of etoposide (1), a topoisomerase II inhibitor, were synthesized and evaluated as potential prodrugs for anticancer therapy. Their activation via hydrolysis mechanisms was determined as a function of pH in buffer solutions, in human serum and in the presence of carboxyl ester hydrolase. Cytotoxicity was determined on various tumor cell lines and compared to the parent compound. On cell lines exhibiting resistance to etoposide we observed an enhanced cytotoxicity of the prodrugs of up to three orders of magnitude. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00801-0
• 作为产物：
  描述：

  2,2-二甲基-1,3-二氧杂烷-4-甲基 氯甲酸 、 依托泊苷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83.5%的产率得到托尼依托泊苷
  参考文献：
  名称：

  Synthesis, Hydrolytic Activation and Cytotoxicity of Etoposide Prodrugs

  摘要：

  Two 4'-propylcarbonoxy derivatives (2,3) of etoposide (1), a topoisomerase II inhibitor, were synthesized and evaluated as potential prodrugs for anticancer therapy. Their activation via hydrolysis mechanisms was determined as a function of pH in buffer solutions, in human serum and in the presence of carboxyl ester hydrolase. Cytotoxicity was determined on various tumor cell lines and compared to the parent compound. On cell lines exhibiting resistance to etoposide we observed an enhanced cytotoxicity of the prodrugs of up to three orders of magnitude. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00801-0

文献信息

• Bioorganic and Medicinal Chemistry Letters 2002, 12, 557-560
  作者：

  DOI：——

  日期：——
• Synthesis, Hydrolytic Activation and Cytotoxicity of Etoposide Prodrugs
  作者：Wolf Wrasidlo、Ulrike Schröder、Kathrin Bernt、Nicole Hübener、Doron Shabat、Gerhard Gaedicke、Holger Lode

  DOI：10.1016/s0960-894x(01)00801-0

  日期：2002.2

  Two 4'-propylcarbonoxy derivatives (2,3) of etoposide (1), a topoisomerase II inhibitor, were synthesized and evaluated as potential prodrugs for anticancer therapy. Their activation via hydrolysis mechanisms was determined as a function of pH in buffer solutions, in human serum and in the presence of carboxyl ester hydrolase. Cytotoxicity was determined on various tumor cell lines and compared to the parent compound. On cell lines exhibiting resistance to etoposide we observed an enhanced cytotoxicity of the prodrugs of up to three orders of magnitude. (C) 2002 Elsevier Science Ltd. All rights reserved.