4-methyl-7-phenoxy-2H-chromen-2-one | 828265-68-5

• 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: 4-methyl-7-phenoxy-2H-chromen-2-one
• 英文别名: 7-phenoxy-4-methylcoumarin；2H-1-Benzopyran-2-one, 4-methyl-7-phenoxy-；4-methyl-7-phenoxychromen-2-one
• CAS: 828265-68-5
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: OFKSFPDEMZWDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-7-phenoxy-2H-chromen-2-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以40%的产率得到4-(bromomethyl)-7-phenoxy-2H-chromen-2-one
  参考文献：
  名称：

  新型有效和选择性芳香化酶抑制剂的设计，合成和3D QSAR。

  摘要：

  报道了一系列新的芳香酶抑制剂的设计，合成和生物学评估，这些抑制剂带有与芴（A），茚并二嗪（B）或香豆素骨架（C）连接的咪唑或三唑环。与17-α-羟化酶/ 17-20裂解酶相比，正确取代的香豆素衍生物显示出最高的芳香酶抑制能力和选择性。通过比较分子场分析（CoMFA / GOLPE 3D QSAR方法）对芳香化酶抑制数据进行建模，导致了具有良好拟合和预测能力（n = 22，ONC = 3，r（2）= 0.949， s = 0.216，而q（2）= 0.715）。

  DOI：

  10.1021/jm049535j
• 作为产物：
  描述：

  间苯二酚 在 磷酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-methyl-7-phenoxy-2H-chromen-2-one
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676

文献信息

• Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications
  作者：Baoxin Zhang、Chunpo Ge、Juan Yao、Yaping Liu、Huichen Xie、Jianguo Fang

  DOI：10.1021/ja5099676

  日期：2015.1.21

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo
• Design, Synthesis, and 3D QSAR of Novel Potent and Selective Aromatase Inhibitors
  作者：Francesco Leonetti、Angelo Favia、Angela Rao、Rosaria Aliano、Anja Paluszcak、Rolf W. Hartmann、Angelo Carotti

  DOI：10.1021/jm049535j

  日期：2004.12.1

  imidazole or triazole ring linked to a fluorene (A), indenodiazine (B), or coumarin scaffold (C) are reported. Properly substituted coumarin derivatives displayed the highest aromatase inhibitory potency and selectivity over 17-alpha-hydroxylase/17-20 lyase. The modeling of the aromatase inhibition data by Comparative Molecular Field Analysis (CoMFA/GOLPE 3D QSAR approach) led to the development of a PLS

  报道了一系列新的芳香酶抑制剂的设计，合成和生物学评估，这些抑制剂带有与芴（A），茚并二嗪（B）或香豆素骨架（C）连接的咪唑或三唑环。与17-α-羟化酶/ 17-20裂解酶相比，正确取代的香豆素衍生物显示出最高的芳香酶抑制能力和选择性。通过比较分子场分析（CoMFA / GOLPE 3D QSAR方法）对芳香化酶抑制数据进行建模，导致了具有良好拟合和预测能力（n = 22，ONC = 3，r（2）= 0.949， s = 0.216，而q（2）= 0.715）。