[(1S,2S,3R,5S,7S,8S,9R,10R,13R)-2,7,9-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-14-oxatetracyclo[11.2.1.01,11.03,8]hexadec-11-en-10-yl] benzoate | 1035113-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(1S,2S,3R,5S,7S,8S,9R,10R,13R)-2,7,9-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-14-oxatetracyclo[11.2.1.01,11.03,8]hexadec-11-en-10-yl] benzoate
• CAS: 1035113-23-5
• 化学式: C₃₃H₄₀O₁₀
• 分子量: 596.675
• InChiKey: CXDRJNFAZGCPIP-JSUXROAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,5S,7S,8S,9R,10R,13R)-2,7,9-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-14-oxatetracyclo[11.2.1.01,11.03,8]hexadec-11-en-10-yl] benzoate 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到[(1S,2S,3S,7S,8S,9R,10R,13R)-2,7,9-triacetyloxy-8,12,15,15-tetramethyl-4-methylidene-5-oxo-14-oxatetracyclo[11.2.1.01,11.03,8]hexadec-11-en-10-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：

  taxchinin A 在 吡啶 、 对甲苯磺酰氯 作用下， 以51.9%的产率得到[(1S,2S,3R,5S,7S,8S,9R,10R,13R)-2,7,9-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-14-oxatetracyclo[11.2.1.01,11.03,8]hexadec-11-en-10-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.