10-deacetylisotaxol | 125354-13-4

• 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: 10-deacetylisotaxol
• 英文别名: Tylvgqknnuhxip-iyavshqlsa-；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2S,3R)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 125354-13-4
• 化学式: C₄₅H₄₉NO₁₃
• 分子量: 811.883
• InChiKey: TYLVGQKNNUHXIP-IYAVSHQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  59
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  215
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 10-deacetylisotaxol 在 吡啶 作用下， 反应 0.5h， 以22%的产率得到2',7-diacetyl-10-deacetylisotaxol
  参考文献：
  名称：

  Conformation of Taxotere® and analogues determined by NMR spectroscopy and molecular modeling studies

  摘要：

  Taxol 1 and Taxotere(R) 2 are antitumor compounds interacting with tubulin proteins. In order to find the best conformational fit to the receptor site, the structures of taxotere and twelve analogues showing various in vitro biological activity on tubulin, have been investigated by H-1 NMR spectroscopy and molecular modeling studies. These structures were compared to that of Taxotere(R) 2 obtained by X-ray analysis. The results obtained from these studies suggest that the most active 2R,3'S compounds possess a conformation in which the benzoate group at C-2 holds the side chain in a defined position due Lo hydrophobic interactions between this group and the N-amido or N-carbonyloxy group at C-3'. This situation together with the presence of hydrogen bonding between 2'OH -3'NH and 2'OH-1'C=O gives rise to a specific orientation of the hydroxyl and phenyl groups at C-2' and C-3'. On the other hand, the 2'S,3'R isomers which display low in vitro biological activity (ie: on tubulin), such as isotaxotere 8, possess a different conformation with no hydrophobic interactions between the side chain and the taxan skeleton.

  DOI：

  10.1016/s0040-4020(01)81822-6
• 作为产物：
  描述：

  Xpsujjsvfgrugm-mwvdqjsfsa- 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到10-deacetylisotaxol
  参考文献：
  名称：

  Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues

  摘要：

  DOI：

  10.1016/s0040-4020(01)81313-2

文献信息

• MANGATAL, L.;ADELINE, M. -T.;GUENARD, D.;GUERITTE-VOEGELEIN, F.;POTIER, P+, TETRAHEDRON, 45,(1989) N3, C. 4177-4190
  作者：MANGATAL, L.、ADELINE, M. -T.、GUENARD, D.、GUERITTE-VOEGELEIN, F.、POTIER, P+

  DOI：——

  日期：——
• Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues
  作者：L. Mangatal、M.-T. Adeline、D. Guénard、F. Guéritte-Voegelein、P. Potier

  DOI：10.1016/s0040-4020(01)81313-2

  日期：1989.1
• Conformation of Taxotere® and analogues determined by NMR spectroscopy and molecular modeling studies
  作者：Joëlle Dubois、Daniel Guénard、Françoise Guéritte-Voegelein、Nourredine Guedira、Pierre Potier、Brigitte Gillet、Jean-Claude Beloeil

  DOI：10.1016/s0040-4020(01)81822-6

  日期：1993.7

  Taxol 1 and Taxotere(R) 2 are antitumor compounds interacting with tubulin proteins. In order to find the best conformational fit to the receptor site, the structures of taxotere and twelve analogues showing various in vitro biological activity on tubulin, have been investigated by H-1 NMR spectroscopy and molecular modeling studies. These structures were compared to that of Taxotere(R) 2 obtained by X-ray analysis. The results obtained from these studies suggest that the most active 2R,3'S compounds possess a conformation in which the benzoate group at C-2 holds the side chain in a defined position due Lo hydrophobic interactions between this group and the N-amido or N-carbonyloxy group at C-3'. This situation together with the presence of hydrogen bonding between 2'OH -3'NH and 2'OH-1'C=O gives rise to a specific orientation of the hydroxyl and phenyl groups at C-2' and C-3'. On the other hand, the 2'S,3'R isomers which display low in vitro biological activity (ie: on tubulin), such as isotaxotere 8, possess a different conformation with no hydrophobic interactions between the side chain and the taxan skeleton.