Desoxypodophyllinsaeure-methylester | 1643-12-5

• 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: Desoxypodophyllinsaeure-methylester
• 英文别名: methyl (5R,6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
• CAS: 1643-12-5
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: MXGHOMGUPJFHLU-DLPLYFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Desoxypodophyllinsaeure-methylester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以24 mg的产率得到9-deoxypodophyllol
  参考文献：
  名称：

  杜松极性提取物中的木脂素

  摘要：

  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。

  DOI：

  10.1016/0031-9422(91)83051-l
• 作为产物：
  描述：

  甲醇 、 去氧鬼臼毒素 在 硫酸 作用下， 反应 24.0h， 以48%的产率得到Desoxypodophyllinsaeure-methylester
  参考文献：
  名称：

  Cytotoxicity against cholangiocarcinoma and HepG2 cell lines of lignan derivatives from Hernandia nymphaeifolia

  摘要：

  Twelve lignan derivatives were synthesized from deoxypodophyllotoxin isolated from Hernandia nymphaeifolia. Cytotoxicity evaluation against cholangiocarcinoma, KKU-100, and HepG2 cell lines showed that compounds 3, 9, 10, and 13 exhibited stronger cytotoxicity than the starting material, 1, with IC50 ranging from 0.42 to 2.01 mu M. Compound 10 displayed interesting activity by showing IC50 values of 0.75 and 0.46 mu M against KKU-100 and HepG2 cell lines, respectively. From these observation, 10 seems to be useful as a lead compound for the development of anticancer agents.

  DOI：

  10.1007/s00044-018-2214-9

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。
• Cytotoxicity against cholangiocarcinoma and HepG2 cell lines of lignan derivatives from Hernandia nymphaeifolia
  作者：Jittra Suthiwong、Jaroon Wandee、Siripit Pitchuanchom、Punchapat Sojikul、Veerapol Kukongviriyapan、Chavi Yenjai

  DOI：10.1007/s00044-018-2214-9

  日期：2018.8

  Twelve lignan derivatives were synthesized from deoxypodophyllotoxin isolated from Hernandia nymphaeifolia. Cytotoxicity evaluation against cholangiocarcinoma, KKU-100, and HepG2 cell lines showed that compounds 3, 9, 10, and 13 exhibited stronger cytotoxicity than the starting material, 1, with IC50 ranging from 0.42 to 2.01 mu M. Compound 10 displayed interesting activity by showing IC50 values of 0.75 and 0.46 mu M against KKU-100 and HepG2 cell lines, respectively. From these observation, 10 seems to be useful as a lead compound for the development of anticancer agents.