dimethyl-4-iso-α-conidendrol | 321747-12-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: dimethyl-4-iso-α-conidendrol
• 英文别名: [(2R,3R,4R)-4-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methanol
• CAS: 321747-12-0
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: LTMZRNBMJLXRNY-GIMINZRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl-4-iso-α-conidendrol 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 3.0h， 以72%的产率得到dimethylanhydro-4-iso-α-conidendrol
  参考文献：
  名称：

  Cytotoxic Responses to Aromatic Ring and Configurational Variations in α-Conidendrin, Podophyllotoxin, and Sikkimotoxin Derivatives

  摘要：

  Derivatives of alpha -conidendrin, podophyllotoxin, and sikkimotoxin were prepared to evaluate the cytotoxic contributions of C-4 configuration and pendant and fused arene substitutions. Dimethyl-alpha -conidendryl alcohol (5), 9-deoxypodophyllol (6), and 9-deoxysikkimol (17) were dehydrated to their respective oxolane derivatives 4, 3, and 9. Diols 5 and 6 were converted via oxabicyclo[3.2.1] octanols 10 and 14 to target oxolanes 8 and 7 where C-4 had been inverted relative to that in 3 and 4. Cytotoxicities of the five oxolanes were determined in two drug-sensitive human leukemia and two multidrug-resistant cell lines expressing P-glycoprotein or multidrug-resistance associated protein (MRP). Changing the pendant arene configuration or replacing a m-methoxy by hydrogen resulted in a 100-fold cytotoxicity loss. Replacing a methylenedioxy group in the fused arene by two methoxy substituents reduced cytotoxicity by 10-fold. Drug-resistant cell lines were equally resistant to compounds 3, 4, 8, and 9 indicating that these four compounds do not serve as substrates of the transport proteins P-glycoprotein and MRP.

  DOI：

  10.1021/jm990563p
• 作为产物：
  描述：

  O-dimethyl-α-retrodendrine 生成 dimethyl-4-iso-α-conidendrol
  参考文献：
  名称：

  BROWN, ERIC;DAUGAN, ALAIN, TETRAHEDRON, 45,(1989) N 1, C. 141-154

  摘要：

  DOI：