[(4R,5R,5aS,6S,8S,9aR)-5,6-diacetyloxy-8-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-4,5,6,7,8,9a-hexahydro-1H-benzo[g]azulen-4-yl] benzoate | 1035113-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(4R,5R,5aS,6S,8S,9aR)-5,6-diacetyloxy-8-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-4,5,6,7,8,9a-hexahydro-1H-benzo[g]azulen-4-yl] benzoate
• CAS: 1035113-28-0
• 化学式: C₂₈H₃₀O₈
• 分子量: 494.541
• InChiKey: BOKYQEQTAFGEPT-VDGBXLALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(4R,5R,5aS,6S,8S,9aR)-5,6-diacetyloxy-8-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-4,5,6,7,8,9a-hexahydro-1H-benzo[g]azulen-4-yl] benzoate 在 pyridinium chlorochromate 作用下， 反应 6.0h， 以45.2%的产率得到[(4R,5R,5aS,6S,9aS)-5,6-diacetyloxy-9-formyl-3,5a-dimethyl-2-oxo-1,4,5,6,7,9a-hexahydrobenzo[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
• 作为产物：
  描述：

  Taxuspinanane B 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以27.5%的产率得到[(5aR,6S,8S,9aR)-6-acetyloxy-8-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-6,7,8,9a-tetrahydro-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