prop-2-enyl (2S,3S,4S,5R,6S)-6-[4-(1-hydroxybut-3-ynyl)-2-nitrophenoxy]-3,4,5-tris(prop-2-enoxycarbonyloxy)oxane-2-carboxylate | 1352435-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-enyl (2S,3S,4S,5R,6S)-6-[4-(1-hydroxybut-3-ynyl)-2-nitrophenoxy]-3,4,5-tris(prop-2-enoxycarbonyloxy)oxane-2-carboxylate
• CAS: 1352435-37-0
• 化学式: C₃₁H₃₃NO₁₆
• 分子量: 675.6
• InChiKey: NEDKXQFRFFNIIX-VWKSRSRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  48
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  217
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S,3S,4S,5R,6S)-6-[4-(1-hydroxybut-3-ynyl)-2-nitrophenoxy]-3,4,5-tris(prop-2-enoxycarbonyloxy)oxane-2-carboxylate 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 prop-2-enyl (2S,3S,4S,5R,6S)-6-[4-[1-[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]carbamoyloxy]but-3-ynyl]-2-nitrophenoxy]-3,4,5-tris(prop-2-enoxycarbonyloxy)oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis and Antitumor Efficacy of a β-Glucuronidase-Responsive Albumin-Binding Prodrug of Doxorubicin

  摘要：

  In this paper we describe the synthesis and biological evaluation of the first beta-glucuronidase-responsive albumin-binding prodrug designed for the selective delivery of doxorubicin at the tumor site. This prodrug leads to superior antitumor efficacy in mice compared to HMR 1826, a well-known glucuronide prodrug of doxorubicin that cannot bind covalently to circulating albumin. Furthermore, this compound inhibits tumor growth in a manner similar to that of doxorubicin while avoiding side effects induced by the free drug.

  DOI：

  10.1021/jm300348r
• 作为产物：
  描述：

  rac-4-(1-hydroxybut-3-yn-1-yl)-2-nitrophenol 在 吡啶 、 咪唑 、 1,1,4,7,10,10-六甲基三亚乙基四胺 、 氢氟酸 、 sodium methylate 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 烯丙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 97.67h， 生成 prop-2-enyl (2S,3S,4S,5R,6S)-6-[4-(1-hydroxybut-3-ynyl)-2-nitrophenoxy]-3,4,5-tris(prop-2-enoxycarbonyloxy)oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis and Antitumor Efficacy of a β-Glucuronidase-Responsive Albumin-Binding Prodrug of Doxorubicin

  摘要：

  In this paper we describe the synthesis and biological evaluation of the first beta-glucuronidase-responsive albumin-binding prodrug designed for the selective delivery of doxorubicin at the tumor site. This prodrug leads to superior antitumor efficacy in mice compared to HMR 1826, a well-known glucuronide prodrug of doxorubicin that cannot bind covalently to circulating albumin. Furthermore, this compound inhibits tumor growth in a manner similar to that of doxorubicin while avoiding side effects induced by the free drug.

  DOI：

  10.1021/jm300348r

文献信息

• Synthesis and Antitumor Efficacy of a β-Glucuronidase-Responsive Albumin-Binding Prodrug of Doxorubicin
  作者：Thibaut Legigan、Jonathan Clarhaut、Brigitte Renoux、Isabelle Tranoy-Opalinski、Arnaud Monvoisin、Jean-Marc Berjeaud、François Guilhot、Sébastien Papot

  DOI：10.1021/jm300348r

  日期：2012.5.10

  In this paper we describe the synthesis and biological evaluation of the first beta-glucuronidase-responsive albumin-binding prodrug designed for the selective delivery of doxorubicin at the tumor site. This prodrug leads to superior antitumor efficacy in mice compared to HMR 1826, a well-known glucuronide prodrug of doxorubicin that cannot bind covalently to circulating albumin. Furthermore, this compound inhibits tumor growth in a manner similar to that of doxorubicin while avoiding side effects induced by the free drug.