6-dimethylamino-2-methyl-benzofuran-3-one | 1153685-77-8

• 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: 6-dimethylamino-2-methyl-benzofuran-3-one
• 英文别名: 6-(Dimethylamino)-2-methyl-1-benzofuran-3-one
• CAS: 1153685-77-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: ZAFPJEBJIRGLJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-dimethylamino-2-methyl-benzofuran-3-one 、 2-甲基-3-乙氧基丙烯醛 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 0.25h， 以70%的产率得到3-(6-dimethylamino-2-methyl-3-oxo-2,3-dihydro-benzofuran-2-yl)-2-methyl-propenal
  参考文献：
  名称：

  Synthesis and Modeling of New Benzofuranone Histone Deacetylase Inhibitors that Stimulate Tumor Suppressor Gene Expression

  摘要：

  New benzofuranones were synthesized and evaluated toward NCI-H661 non-small cell lung cancer cells. Benzamide derivatives possessed micromolar anti proliferative and histone deacetylase inhibitory activities and modulate histone H4 acetylation. Hydroxamic acids were found to be potent nanomolar anti proliferative agents and HDAC inhibitors. Computational analysis presented a rationale for the activities of the hydroxamate derivatives. Impact of the HDAC inhibition on the expression of E-cadherin and the SEMA3F tumor suppressor genes revealed new promising compounds for lung cancer treatments.

  DOI：

  10.1021/jm9002439
• 作为产物：
  描述：

  p-(dimethylamino)salicylic acid methyl ester 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 6-dimethylamino-2-methyl-benzofuran-3-one
  参考文献：
  名称：

  Hammet Constants Effects in Microwave Cascade Etherification-Cyclization-Krapcho Reaction to Access [2,3]-Dihydrobenzofuran-3-ones from Salicylic Derivatives

  摘要：

  Two methods were evaluated for the synthesis of substituted [2,3]-dihydro-2-methyl-benzofuran-3-ones from corresponding salicylate esters under microwave irradiation. A two-step sequence via ether intermediates was convenient for various substituted salicylate derivatives, while the second strategy involving a one-pot procedure was efficient for electron-donating substituted salicylates. Results allowed correlation of the Hammett constants effects in the intramolecular cyclization of O-ethoxycarbonyl ether of salicylic esters.

  DOI：

  10.1080/00397911.2010.533806

文献信息

• Hammet Constants Effects in Microwave Cascade Etherification-Cyclization-Krapcho Reaction to Access [2,3]-Dihydrobenzofuran-3-ones from Salicylic Derivatives
  作者：Daniel Farran、Philippe Bertrand

  DOI：10.1080/00397911.2010.533806

  日期：2012.4.1

  Two methods were evaluated for the synthesis of substituted [2,3]-dihydro-2-methyl-benzofuran-3-ones from corresponding salicylate esters under microwave irradiation. A two-step sequence via ether intermediates was convenient for various substituted salicylate derivatives, while the second strategy involving a one-pot procedure was efficient for electron-donating substituted salicylates. Results allowed correlation of the Hammett constants effects in the intramolecular cyclization of O-ethoxycarbonyl ether of salicylic esters.
• Synthesis and Modeling of New Benzofuranone Histone Deacetylase Inhibitors that Stimulate Tumor Suppressor Gene Expression
  作者：Cédric Charrier、Jonathan Clarhaut、Jean-Pierre Gesson、Guillermina Estiu、Olaf Wiest、Joëlle Roche、Philippe Bertrand

  DOI：10.1021/jm9002439

  日期：2009.5.14

  New benzofuranones were synthesized and evaluated toward NCI-H661 non-small cell lung cancer cells. Benzamide derivatives possessed micromolar anti proliferative and histone deacetylase inhibitory activities and modulate histone H4 acetylation. Hydroxamic acids were found to be potent nanomolar anti proliferative agents and HDAC inhibitors. Computational analysis presented a rationale for the activities of the hydroxamate derivatives. Impact of the HDAC inhibition on the expression of E-cadherin and the SEMA3F tumor suppressor genes revealed new promising compounds for lung cancer treatments.