[(3aR,4S,9R,9aR)-6,7-dimethoxy-1-oxo-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-4-yl] 2-phenylacetate | 1417534-24-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: [(3aR,4S,9R,9aR)-6,7-dimethoxy-1-oxo-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-4-yl] 2-phenylacetate
• CAS: 1417534-24-7
• 化学式: C₃₁H₃₂O₉
• 分子量: 548.59
• InChiKey: MNNWQAHBHHWJQT-MHTDFPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6,7-O,O-demethylenepodophyllotoxin 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 potassium carbonate 、 sodium iodide 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 生成 [(3aR,4S,9R,9aR)-6,7-dimethoxy-1-oxo-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-4-yl] 2-phenylacetate
  参考文献：
  名称：

  Synthesis and Quantitative Structure–Activity Relationship (QSAR) Study of Novel 4-Acyloxypodophyllotoxin Derivatives Modified in the A and C Rings as Insecticidal Agents

  摘要：

  In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized three series of novel 4-acyloxy compounds derived from podophyllotoxin modified in the A and C rings, which is isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum hexandrum. Their insecticidal activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata in vivo. Compound 9g displayed the best promising insecticidal activity. It revealed that cleavage of the 6,7-methylenedioxy group of podophyllotoxin will lead to a less active compound and that the C-4 position of podophyllotoxin was the important modification location. A quantitative structure activity relationship (QSAR) model was developed by genetic algorithm combined with multiple linear regression (GA-MLR). For this model, the squared correlation coefficient (R-2) is 0.914, the leave-one-out cross-validation correlation coefficient (Q(LOO)(2)) is 0.881, and the root-mean-square error (RMSE) is 0.024. Five descriptors, BEHm2, Mor14v, Wap, G1v, and RDF020e, are likely to influence the biological activity of these compounds. Among them, two important ones are BEHm2 and Mor14v. This study will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.

  DOI：

  10.1021/jf305011n

文献信息

• Synthesis and Quantitative Structure–Activity Relationship (QSAR) Study of Novel 4-Acyloxypodophyllotoxin Derivatives Modified in the A and C Rings as Insecticidal Agents
  作者：Shuzhen He、Yonghua Shao、Lingling Fan、Zhiping Che、Hui Xu、Xiaoyan Zhi、Juanjuan Wang、Xiaojun Yao、Huan Qu

  DOI：10.1021/jf305011n

  日期：2013.1.23

  In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized three series of novel 4-acyloxy compounds derived from podophyllotoxin modified in the A and C rings, which is isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum hexandrum. Their insecticidal activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata in vivo. Compound 9g displayed the best promising insecticidal activity. It revealed that cleavage of the 6,7-methylenedioxy group of podophyllotoxin will lead to a less active compound and that the C-4 position of podophyllotoxin was the important modification location. A quantitative structure activity relationship (QSAR) model was developed by genetic algorithm combined with multiple linear regression (GA-MLR). For this model, the squared correlation coefficient (R-2) is 0.914, the leave-one-out cross-validation correlation coefficient (Q(LOO)(2)) is 0.881, and the root-mean-square error (RMSE) is 0.024. Five descriptors, BEHm2, Mor14v, Wap, G1v, and RDF020e, are likely to influence the biological activity of these compounds. Among them, two important ones are BEHm2 and Mor14v. This study will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.