9-deoxypodophyllol | 31104-02-6

• 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: 9-deoxypodophyllol
• 英文别名: (5R)-6c,7t-bis-hydroxymethyl-5r-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole；(5R)-6c,7t-Bis-hydroxymethyl-5r-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol；Deoxyopodophyllol；[(5R,6R,7R)-6-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxol-7-yl]methanol
• CAS: 31104-02-6
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: JVSYCTMODBCSAF-WDUKFBBWSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  556.5±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 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：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-deoxypodophyllol 在 palladium on activated charcoal 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 6,8-二溴-4-氧代-4H-1-苯并吡喃-3-甲醛
  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：

  去氧鬼臼毒素 在 lithium aluminium tetrahydride 作用下， 生成 9-deoxypodophyllol
  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

• Lignans from polar extracts ofJuniperus thurifera
  作者：Arturo San Feliciano、Jose M. Miguel Del Corral、Jose L. Lopez、Beatriz De Pascual-Teresa

  DOI：10.1016/0031-9422(91)83051-l

  日期：1992.1

  Abstract Three new natural lignans, methyl deoxypodophyllotoxinate, podophyllotoxinic acid and 7β-hydroxydihydrosesamin, 11 known lignans and two cinnamyl alcohols were isolated and identified from a chloroform extract of Juniperus thurifera leaves. Assignment of the 13 C NMR spectrum of β-methyl peltatin B was also performed through direct and long-range heteronuclear 2D NMR analysis, amending previous

  摘要 从杜松叶氯仿提取物中分离鉴定出3种新的天然木脂素，即脱氧鬼臼毒素甲酯、鬼臼毒素酸和7β-羟基二氢芝麻素，11种已知木脂素和2种肉桂醇。β-甲基peltatin B 的 13 C NMR 光谱的分配也通过直接和远程异核 2D 核磁共振分析进行，修改了以前的分配。
• Modes of Methyleneoxy Bridging and Their Effect on Tetrahydronaphthalene Lignan Cytotoxicity
  作者：Robert T. LaLonde、Frank Ramdayal、Anatole Sarko、Koichi Yanai、Mianji Zhang

  DOI：10.1021/jm020158p

  日期：2003.3.1

  Dioxatricyclodecane, oxabicyclooctane, and benzodihydropyran derivatives of alpha-conidendrin (ACON), podophyllotoxin (PT), and sikkimotoxin (SK) were prepared to learn which methyleneoxy bridging modes and arene and aryl substituents coincided with high cytotoxicity. PT-derived dioxatricyclodecane 14 showed in vitro activity at 10(-8) M. SK analogue 12 was less active, and ACON analogue 11 was inactive at 10(-4) M. In vivo intraperitoneal and subcutaneous activities of 14 were observed. In vitro cytotoxicities were higher for oxabicyclooctanes when hydroxymethyl group and methyleneoxy bridge were cis, as in deoxypicropodophyllin analog 20, rather than trans, as in PT analogue 5. Acetylation of the hydroxymethyl group of 20 lowered activities, whereas acetylation of 5 increased or lowered activities. Reduction of the hydroxymethyl group of 5 to a methyl group increased cytotoxicities. Molecular dynamics indicated the THN scaffold of benzodihydropyrans was conformationally mobile, but scaffolds of oxabicyclooctanes and dioxatricyclodecanes were immobile. Each of three PT-benzodihydropyrans was less active than its oxabicyclooctane counterpart.
• Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans²
  作者：Anthony W. Schrecker、Jonathan L. Hartwell

  DOI：10.1021/ja01607a063

  日期：1955.1
• 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.