4,6-dimethoxy-3-methyl-benzofuran-2-carboxylic acid | 855162-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4,6-dimethoxy-3-methyl-benzofuran-2-carboxylic acid
• 英文别名: 4,6-Dimethoxy-3-methyl-benzofuran-2-carbonsaeure；4,6-Dimethoxy-3-methyl-1-benzofuran-2-carboxylic acid
• CAS: 855162-39-9
• 化学式: C₁₂H₁₂O₅
• mdl: MFCD12079194
• 分子量: 236.224
• InChiKey: NZIGXAHSWJTBRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-3-methyl-benzofuran-2-carboxylic acid 在 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of novel 6-hydroxy-4-methoxy-3-methylbenzofuran-7-carboxamide derivatives as potent Mnks inhibitors by fragment-based drug design

  摘要：

  A novel series of 6-hydroxy-4-methoxy-3-methylbenzofuran-7-carboxamide derivatives featured with various C-2 substituents were designed and synthesized as Mnks inhibitors through fragment-based drug design. Among them, 5b, 51, 5o and 8k showed the best Mnk2 inhibitory activity with IC 50 values of 1.45, 1.16, 3.55 and 0.27 mu M, respectively. And these compounds inhibited the activity of Mnkl at the same time. Furthermore, compounds 50 and 8k exhibited anti-proliferative effects to human leukemia cancer THP-1 and MOLM-13 cell lines and colon cancer HCT-116 cell line. Moreover, Western blot assay suggested that 8k could decrease the levels of p-eIF4E in a dose-dependent manner in HCT-116 cells. Docking studies demonstrated strong interactions between 8k and Mnk2. Therefore, this unique benzofuran scaffold demonstrated great potential to be further explored as potent Mnks inhibitors with improved potency. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2018.05.004
• 作为产物：
  描述：

  (3,5-Dimethoxy-phenoxy)-aceton 在 盐酸 、 potassium permanganate 、 乙醚 、 硫酸 、 丙酮 作用下， 生成 4,6-dimethoxy-3-methyl-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  61.松萝酸。第六部分 邻二甲基次膦酸的合成

  摘要：

  DOI：

  10.1039/jr9380000306

文献信息

• v. Kostanecki; Tambor, Chemische Berichte, 1909, vol. 42, p. 908
  作者：v. Kostanecki、Tambor

  DOI：——

  日期：——
• US3940417A
  申请人：——

  公开号：US3940417A

  公开（公告）日：1976-02-24
• US4009994A
  申请人：——

  公开号：US4009994A

  公开（公告）日：1977-03-01
• Design and synthesis of novel 6-hydroxy-4-methoxy-3-methylbenzofuran-7-carboxamide derivatives as potent Mnks inhibitors by fragment-based drug design
  作者：Shuxiang Wang、Bo Li、Bo Liu、Min Huang、Deyi Li、Lihong Guan、Jie Zang、Dan Liu、Linxiang Zhao

  DOI：10.1016/j.bmc.2018.05.004

  日期：2018.9

  A novel series of 6-hydroxy-4-methoxy-3-methylbenzofuran-7-carboxamide derivatives featured with various C-2 substituents were designed and synthesized as Mnks inhibitors through fragment-based drug design. Among them, 5b, 51, 5o and 8k showed the best Mnk2 inhibitory activity with IC 50 values of 1.45, 1.16, 3.55 and 0.27 mu M, respectively. And these compounds inhibited the activity of Mnkl at the same time. Furthermore, compounds 50 and 8k exhibited anti-proliferative effects to human leukemia cancer THP-1 and MOLM-13 cell lines and colon cancer HCT-116 cell line. Moreover, Western blot assay suggested that 8k could decrease the levels of p-eIF4E in a dose-dependent manner in HCT-116 cells. Docking studies demonstrated strong interactions between 8k and Mnk2. Therefore, this unique benzofuran scaffold demonstrated great potential to be further explored as potent Mnks inhibitors with improved potency. (C) 2018 Published by Elsevier Ltd.
• 61. Usnic acid. Part VI. The synthesis of O-dimethylpyrousnic acid
  作者：Harold F. Birch、Alexander Robertson

  DOI：10.1039/jr9380000306

  日期：——