3-(4-Methoxy-3-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,2,5-oxadiazole | 852990-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-Methoxy-3-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,2,5-oxadiazole
• CAS: 852990-44-4
• 化学式: C₁₈H₁₇N₃O₇
• 分子量: 387.349
• InChiKey: OOTANXBAFHZIEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxy-3-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,2,5-oxadiazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到2-Methoxy-5-[4-(3,4,5-trimethoxyphenyl)-1,2,5-oxadiazol-3-yl]aniline
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurazans

  摘要：

  Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.

  DOI：

  10.1021/jm049096o
• 作为产物：
  描述：

  (E)-3-(3'-nitro-4'-dimethoxyphenyl)-2-(3'',4'',5''-trimethoxyphenyl)acrylic acid 在 吡啶 、 potassium permanganate 、 偶氮二甲酸二叔丁酯 、 盐酸羟胺 、 乙酸酐 、 铜 、 三苯基膦 作用下， 以 喹啉 、 乙醇 、 甲苯 为溶剂， 反应 52.0h， 生成 3-(4-Methoxy-3-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,2,5-oxadiazole
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurazans

  摘要：

  Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.

  DOI：

  10.1021/jm049096o

文献信息

• Synthesis and Cytotoxic Evaluation of Combretafurazans
  作者：Gian Cesare Tron、Francesca Pagliai、Erika Del Grosso、Armando A. Genazzani、Giovanni Sorba

  DOI：10.1021/jm049096o

  日期：2005.5.1

  Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.