[(1S,3S,7S,8S,9R,10R,13R)-7,9-diacetyloxy-4-formyl-8,12,15,15-tetramethyl-14-oxatetracyclo[11.2.1.01,11.03,8]hexadeca-4,11-dien-10-yl] benzoate | 1035113-25-7

• 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: [(1S,3S,7S,8S,9R,10R,13R)-7,9-diacetyloxy-4-formyl-8,12,15,15-tetramethyl-14-oxatetracyclo[11.2.1.01,11.03,8]hexadeca-4,11-dien-10-yl] benzoate
• CAS: 1035113-25-7
• 化学式: C₃₁H₃₆O₈
• 分子量: 536.622
• InChiKey: QXTQIKOVOYSLHF-ZKEQFEGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(1S,3R,5S,7S,8S,9R,10R,13R)-7,9-diacetyloxy-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50%的产率得到[(1S,3S,7S,8S,9R,10R,13R)-7,9-diacetyloxy-4-formyl-8,12,15,15-tetramethyl-14-oxatetracyclo[11.2.1.01,11.03,8]hexadeca-4,11-dien-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