{2-[2-(2-(doxorubicin-3'-N-yl)carbonylmethoxy-acetylamino)-ethylcarbamoyl]methoxy}-acetic acid N-hydroxysuccinimidyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: {2-[2-(2-(doxorubicin-3'-N-yl)carbonylmethoxy-acetylamino)-ethylcarbamoyl]methoxy}-acetic acid N-hydroxysuccinimidyl ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 2-[2-[2-[[2-[2-[[(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]amino]-2-oxoethoxy]acetyl]amino]ethylamino]-2-oxoethoxy]acetate
• 化学式: C₄₁H₄₆N₄O₂₀
• 分子量: 914.831
• InChiKey: IHBADKOZEHVVHY-JYTNDPEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  65
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  350
• 氢给体数：
  8
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  {[2-(2-carboxymethoxy-acetylamino)-ethylcarbamoyl]methoxy}-acetic acid 在 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 {2-[2-(2-(doxorubicin-3'-N-yl)carbonylmethoxy-acetylamino)-ethylcarbamoyl]methoxy}-acetic acid N-hydroxysuccinimidyl ester
  参考文献：
  名称：

  Efficient One-Pot Synthesis of Doxorubicin Conjugates Through Its Amino Group to Melanotransferrin P97

  摘要：

  The amino group of doxorubicin I is reacted with bis-NHS-ester linkers 6, or anhydrides 13 to offer in high yield modified doxorubicins 7-12 and 14-16, respectively. Compounds 7-12 are mono-NHS-esters, and can be directly coupled with melanotransferrin (p97), a useful vector with the ability to cross the blood-brain barrier, to yield the expected doxorubicin-p97 conjugates. Upon activating the carboxylic group with BTTU, compound 14-16 could be used in the same reaction. Structurally, the amino group of doxorubicin is covalently bonded to the amino groups of p97. The conjugates are potential candidates for treatment of brain tumors.

  DOI：

  10.1081/scc-120021829