6-(4-(dimethylamino)phenyl)-2H-chromen-2-one | 1337936-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-(4-(dimethylamino)phenyl)-2H-chromen-2-one
• 英文别名: 6-[4-(Dimethylamino)phenyl]chromen-2-one
• CAS: 1337936-09-0
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: IRBVKAQSCHBAEF-UHFFFAOYSA-N

物化性质

• 沸点：
  470.6±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  乙醇 、 6-(4-(dimethylamino)phenyl)-2H-chromen-2-one 、 氰乙酸乙酯 在 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以37%的产率得到prop-2-yn-1-yl 2-amino-6-(4-(dimethylamino)phenyl)-4-(2-oxo-2-(prop-2-yn-1-yloxy)ethyl)-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment

  摘要：

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.

  DOI：

  10.1021/jm300515q
• 作为产物：
  描述：

  2-O-acetyl-4-bromosalicylaldehyde 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 18-冠醚-6 、 O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 、 双(三甲基硅烷基)氨基钾 、 cesium fluoride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 6-(4-(dimethylamino)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  6-Arylcoumarins as Novel Nonsteroidal Type Progesterone Antagonists: An Example with Receptor-Binding-Dependent Fluorescence

  摘要：

  Various 6-arylcoumarin derivatives were designed and synthesized as candidate nonsteroidal type progesterone antagonists. 6-Bromocoumarin derivatives were prepared from the corresponding 4-substituted 2-acetoxy-5-bromobenzaldehyde by employing the Still-Gennari modification of the Horner-Wadsworth-Emmons olefination reaction and were converted to 6-arylcoumarins by means of Suzuki-Miyaura cross-coupling reactions. The biological activities of these coumarin derivatives were evaluated by means of alkaline phosphatase assay in the T47D human breast carcinoma cell line. Among the synthesized compounds, 36 (IC(50) = 0.12 mu M) and 38 (IC(50) = 0.06 mu M), bearing a five-membered heterocycle, showed potent PR antagonist activity. Competitive binding assay showed that compounds 8 and 34 have potent PR binding affinity. The fluorescence of compound 8 was dependent on the solvent properties and was increased in the presence of PR ligand binding domain. This property might be applicable to the development of fluorescence probes for studies on PR.

  DOI：

  10.1021/jm2005404

文献信息

• 一种香豆素型有机三阶非线性光学材料及其制备与应用
  申请人：汕头大学

  公开号：CN109776471B

  公开（公告）日：2023-03-10

  本发明涉及一种香豆素型有机三阶非线性光学材料，以香豆素为核心基团，在所述核心基团的6位处连接芳基胺衍生物，所述芳基胺衍生物包括N,N‑二甲基苯和三苯胺以及咔唑苯基。制备主要包括：将6位被溴取代的香豆素衍生物、硼酸频那醇酯的芳基胺衍生物和碳酸钾加入溶剂中溶解；通氮气30min，加入四三苯基膦钯催化剂，加热到80～100℃，1000～1200r/min，反应6～24h；用二氯甲烷和蒸馏水分多次萃取，分液，干燥；将得到的粗产物分离纯化。本发明在香豆素的6位上引入芳基胺衍生物，形成大的D‑π‑A构型，有利于增加香豆素分子的非线性吸收系数和双光子吸收截面值，可应用于三阶非线性光学材料。而且本发明的制备方法简单，易操作，原料易得、成本低，具有较大的应用价值。
• Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4<i>H</i>-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment
  作者：Gopalakrishnan Aridoss、Bo Zhou、David L. Hermanson、Nicholas P. Bleeker、Chengguo Xing

  DOI：10.1021/jm300515q

  日期：2012.6.14

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.
• 6-Arylcoumarins as Novel Nonsteroidal Type Progesterone Antagonists: An Example with Receptor-Binding-Dependent Fluorescence
  作者：Haruka Sakai、Tomoya Hirano、Shuichi Mori、Shinya Fujii、Hiroyuki Masuno、Marie Kinoshita、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1021/jm2005404

  日期：2011.10.27

  Various 6-arylcoumarin derivatives were designed and synthesized as candidate nonsteroidal type progesterone antagonists. 6-Bromocoumarin derivatives were prepared from the corresponding 4-substituted 2-acetoxy-5-bromobenzaldehyde by employing the Still-Gennari modification of the Horner-Wadsworth-Emmons olefination reaction and were converted to 6-arylcoumarins by means of Suzuki-Miyaura cross-coupling reactions. The biological activities of these coumarin derivatives were evaluated by means of alkaline phosphatase assay in the T47D human breast carcinoma cell line. Among the synthesized compounds, 36 (IC(50) = 0.12 mu M) and 38 (IC(50) = 0.06 mu M), bearing a five-membered heterocycle, showed potent PR antagonist activity. Competitive binding assay showed that compounds 8 and 34 have potent PR binding affinity. The fluorescence of compound 8 was dependent on the solvent properties and was increased in the presence of PR ligand binding domain. This property might be applicable to the development of fluorescence probes for studies on PR.