[(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-trien-12-yl]-methanol | 321747-11-9

• 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: [(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-trien-12-yl]-methanol
• 英文别名: [(1S,9R,12R)-1-(3,4-dimethoxyphenyl)-4,5-dimethoxy-11-oxatricyclo[7.2.1.02,7]dodeca-2,4,6-trien-12-yl]methanol
• CAS: 321747-11-9
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: CIQMFHJWBNOVQL-JKXTWKSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-trien-12-yl]-methanol 在 10percent Pd/C 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.9h， 生成 r-1-(3,4-dimethoxyphenyl)-t-2,c-3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene
  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：

  (d,l)α-conidendrin 在 lithium aluminium tetrahydride 、 hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-trien-12-yl]-methanol
  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

文献信息

• Cytotoxic Responses to Aromatic Ring and Configurational Variations in α-Conidendrin, Podophyllotoxin, and Sikkimotoxin Derivatives
  作者：Anne Dantzig、Robert T. LaLonde、Frank Ramdayal、Robert L. Shepard、Koichi Yanai、Mianji Zhang

  DOI：10.1021/jm990563p

  日期：2001.1.1

  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.