5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl | 851983-58-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 邻苯二甲酸异喹啉类
• 英文名称: 5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl
• 英文别名: [(1S)-5-methoxy-1-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3-oxo-1H-2-benzofuran-4-yl] trifluoromethanesulfonate
• CAS: 851983-58-9
• 化学式: C₂₂H₂₀F₃NO₉S
• 分子量: 531.463
• InChiKey: WJUCVILTNHIWKM-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl 在 palladium on activated charcoal barium dihydroxide 、 2-(2^'-di-tert-butylphosphine)biphenylpalladium(II) acetate 、 三氟甲苯 、 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 8.25h， 生成 7-amino-6-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Identification of Novel and Improved Antimitotic Agents Derived from Noscapine

  摘要：

  Analogues of the natural product noscapine were synthesized and their potential as antitumor agents evaluated. The discovery of a novel regioselective 0-demethylation facilitated the synthesis of the potent aniline 6, which arrests mammalian cells in the G2/M phase of the cell cycle at 0.1 mu M and also affects tubulin polymerization. Aniline 6 is orally bioavailable and is 250-fold more potent than noscapine in reducing cell proliferation in rapidly dividing cells.

  DOI：

  10.1021/jm050674q
• 作为产物：
  描述：

  那可汀 在 吡啶 、 甲基溴化镁 、 苯甲醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 生成 5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl
  参考文献：
  名称：

  Identification of Novel and Improved Antimitotic Agents Derived from Noscapine

  摘要：

  Analogues of the natural product noscapine were synthesized and their potential as antitumor agents evaluated. The discovery of a novel regioselective 0-demethylation facilitated the synthesis of the potent aniline 6, which arrests mammalian cells in the G2/M phase of the cell cycle at 0.1 mu M and also affects tubulin polymerization. Aniline 6 is orally bioavailable and is 250-fold more potent than noscapine in reducing cell proliferation in rapidly dividing cells.

  DOI：

  10.1021/jm050674q

文献信息

• Benzo[1,3]dioxole compounds, pharmaceutical compositions thereof, and processes of making and using the same
  申请人：Bennani Youssef

  公开号：US20050049278A1

  公开（公告）日：2005-03-03

  The present invention relates to benzo[1,3]dioxole compounds and pharmaceutical compositions containing such compounds. These compounds and compositions may be made by various methods. These compounds and compositions may be used to treat disorders and diseases such as cancer.

  本发明涉及苯并[1,3]二噁烷化合物和含有这种化合物的药物组合物。这些化合物和组合物可以通过各种方法制备。这些化合物和组合物可用于治疗癌症等疾病和疾病。
• Discovery of S-Phase Arresting Agents Derived from Noscapine
  作者：James T. Anderson、Anthony E. Ting、Sherry Boozer、Kurt R. Brunden、Joel Danzig、Tom Dent、John J. Harrington、Steven M. Murphy、Rob Perry、Amy Raber、Stephen E. Rundlett、Jianmin Wang、Nancy Wang、Youssef L. Bennani

  DOI：10.1021/jm0494220

  日期：2005.4.1

  Analogues of the natural product noscapine were synthesized, and their potential as antitumor agents were examined. The discovery of a novel regio- and stereoselective O-demethylation led to the synthesis of several O-alkylated analogues that induced an unexpected S-phase arrest of mammalian cells. Compound 4a was the most potent analogue inhibiting cell proliferation at an EC50 of 1.9 mu M.
• Identification of Novel and Improved Antimitotic Agents Derived from Noscapine
  作者：James T. Anderson、Anthony E. Ting、Sherry Boozer、Kurt R. Brunden、Chris Crumrine、Joel Danzig、Tom Dent、Laurel Faga、John J. Harrington、William F. Hodnick、Steven M. Murphy、Gary Pawlowski、Robert Perry、Amy Raber、Stephen E. Rundlett、Alain Stricker-Krongrad、Jianmin Wang、Youssef L. Bennani

  DOI：10.1021/jm050674q

  日期：2005.11.1

  Analogues of the natural product noscapine were synthesized and their potential as antitumor agents evaluated. The discovery of a novel regioselective 0-demethylation facilitated the synthesis of the potent aniline 6, which arrests mammalian cells in the G2/M phase of the cell cycle at 0.1 mu M and also affects tubulin polymerization. Aniline 6 is orally bioavailable and is 250-fold more potent than noscapine in reducing cell proliferation in rapidly dividing cells.