[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-triacetyloxy-1-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 848250-67-9

• 英文名称: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-triacetyloxy-1-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 848250-67-9
• 化学式: C₄₂H₄₆O₁₄
• 分子量: 774.819
• InChiKey: DCDWTAWIBLUSTQ-FWZPTVMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  198
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-triacetyloxy-1-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 、 邻甲氧基苯甲酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以94%的产率得到[4-[(E)-3-oxo-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-triacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-9-yl]oxy]prop-1-enyl]phenyl] 2-methoxybenzoate
  参考文献：
  名称：

  Design, Synthesis and Structure−Activity Relationships of Novel Taxane-Based Multidrug Resistance Reversal Agents

  摘要：

  A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure-activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonyleinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.

  DOI：

  10.1021/jm049483y
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氟化氢吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-triacetyloxy-1-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Design, Synthesis and Structure−Activity Relationships of Novel Taxane-Based Multidrug Resistance Reversal Agents

  摘要：

  A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure-activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonyleinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.

  DOI：

  10.1021/jm049483y