[(2R,6S,7R,9S,11R,14S,15R,16S,17S,19S)-14-acetyloxy-17,19-dihydroxy-4,4,20,21,21-pentamethyl-3,5,12-trioxahexacyclo[15.3.1.02,6.07,9.07,15.011,14]henicos-1(20)-en-16-yl] benzoate | 184586-12-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(2R,6S,7R,9S,11R,14S,15R,16S,17S,19S)-14-acetyloxy-17,19-dihydroxy-4,4,20,21,21-pentamethyl-3,5,12-trioxahexacyclo[15.3.1.02,6.07,9.07,15.011,14]henicos-1(20)-en-16-yl] benzoate
• CAS: 184586-12-7
• 化学式: C₃₂H₄₀O₉
• 分子量: 568.664
• InChiKey: PMTHMIQBRFUGPJ-JJWUYKBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,6S,7R,9S,11R,14S,15R,16S,17S,19S)-14-acetyloxy-17,19-dihydroxy-4,4,20,21,21-pentamethyl-3,5,12-trioxahexacyclo[15.3.1.02,6.07,9.07,15.011,14]henicos-1(20)-en-16-yl] benzoate 在 氟化氢吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 [(2R,6S,7R,9S,11R,14S,15R,16S,17S,19S)-14-acetyloxy-17-hydroxy-19-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyridin-4-ylpropanoyl]oxy-4,4,20,21,21-pentamethyl-3,5,12-trioxahexacyclo[15.3.1.02,6.07,9.07,15.011,14]henicos-1(20)-en-16-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 三氟甲磺酸酐 、 silica gel 、 对甲苯磺酸 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.0h， 生成 [(2R,6S,7R,9S,11R,14S,15R,16S,17S,19S)-14-acetyloxy-17,19-dihydroxy-4,4,20,21,21-pentamethyl-3,5,12-trioxahexacyclo[15.3.1.02,6.07,9.07,15.011,14]henicos-1(20)-en-16-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5