[(2S,4R,5R,5aS,6S,8S,9aR,10S,10aS)-5,6,10-triacetyloxy-2,8-bis[[tert-butyl(dimethyl)silyl]oxy]-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate | 1035113-19-9

• 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: [(2S,4R,5R,5aS,6S,8S,9aR,10S,10aS)-5,6,10-triacetyloxy-2,8-bis[[tert-butyl(dimethyl)silyl]oxy]-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate
• CAS: 1035113-19-9
• 化学式: C₄₅H₇₀O₁₁Si₂
• 分子量: 843.215
• InChiKey: JIWBRGSDSABXTE-SJLLEOSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 taxchinin A 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以23%的产率得到[(2S,4R,5R,5aS,6S,8S,9aR,10S,10aS)-5,6,10-triacetyloxy-2-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate
  参考文献：
  名称：

  Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol

  摘要：

  Twenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22 mu M. 5-Oxo-13-TBDMS-taxchinin A (11) and5-oxo-13,15-epoxy-13-epi-taxchinin A (15) are the most potent derivatives, with IC(50) at 0.48 and 0.75 mu M, respectively. The structure - activity relationship (SAR) of these compounds established that exocyclic unsaturated ketone at ring C is the key structural element for the activity, while the alpha,beta-unsaturated ketone positioned at ring A has no effect for the activity. The significant cytotoxicity of derivatives 11 and 15 may be due to the conformational change in the taxane rings. The 3D-QSAR study was conducted on this series of compounds, which provided optimal predictive comparative molecular field (CoM-FA) model with cross-validated r(2) (q(2)) value of 0.64. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.041

文献信息

• Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol
  作者：Yu Zhao、Na Guo、Li-Guang Lou、Yu-Wen Cong、Li-Yan Peng、Qin-Shi Zhao

  DOI：10.1016/j.bmc.2008.03.041

  日期：2008.5

  Twenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22 mu M. 5-Oxo-13-TBDMS-taxchinin A (11) and5-oxo-13,15-epoxy-13-epi-taxchinin A (15) are the most potent derivatives, with IC(50) at 0.48 and 0.75 mu M, respectively. The structure - activity relationship (SAR) of these compounds established that exocyclic unsaturated ketone at ring C is the key structural element for the activity, while the alpha,beta-unsaturated ketone positioned at ring A has no effect for the activity. The significant cytotoxicity of derivatives 11 and 15 may be due to the conformational change in the taxane rings. The 3D-QSAR study was conducted on this series of compounds, which provided optimal predictive comparative molecular field (CoM-FA) model with cross-validated r(2) (q(2)) value of 0.64. (c) 2008 Elsevier Ltd. All rights reserved.