3-[bromo-(4-nitrophenyl)methyl]chromen-4-one | 869886-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-[bromo-(4-nitrophenyl)methyl]chromen-4-one
• CAS: 869886-56-6
• 化学式: C₁₆H₁₀BrNO₄
• 分子量: 360.164
• InChiKey: AOUPEHRQVKXETM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[bromo-(4-nitrophenyl)methyl]chromen-4-one 以 乙腈 为溶剂， 反应 7.0h， 生成 3-[(R)-1H-imidazol-1-yl(4-nitrophenyl)methyl]-4H-chromen-4-one
  参考文献：
  名称：

  Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach

  摘要：

  To identify enantioselective nonsteroidal aromatase inhibitors, a multidisciplinary medicinal chemistry approach was pursued. First, our earlier CoMFA model [Bioorg. Med. Chem. 1998, 6, 377-3881 was extended taking purposely into account previously discovered enantioselective aromatase inhibitors. The 3D QSAR model was then exploited to design chiral ligands, whose configurational assignment was obtained, after HPLC separation, by means of a combination of circular dichroism measurements and time dependent density functional calculations. Finally, the new enantiomeric inhibitors were separately tested to ascertain both their potency against the cytochrome P450 aromatase (CYP19; EC1.14.14.1), and their selectivity relative to another enzyme of the P450 family. A satisfactory agreement between experimental and predicted data allowed us to assert that a properly built "enantioselective CoMFA model" might constitute a useful tool for addressing enantioselective ligands design.

  DOI：

  10.1021/jm058042r
• 作为产物：
  描述：

  对硝基苯甲醛 在 哌啶 、 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， 反应 9.0h， 生成 3-[bromo-(4-nitrophenyl)methyl]chromen-4-one
  参考文献：
  名称：

  Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach

  摘要：

  To identify enantioselective nonsteroidal aromatase inhibitors, a multidisciplinary medicinal chemistry approach was pursued. First, our earlier CoMFA model [Bioorg. Med. Chem. 1998, 6, 377-3881 was extended taking purposely into account previously discovered enantioselective aromatase inhibitors. The 3D QSAR model was then exploited to design chiral ligands, whose configurational assignment was obtained, after HPLC separation, by means of a combination of circular dichroism measurements and time dependent density functional calculations. Finally, the new enantiomeric inhibitors were separately tested to ascertain both their potency against the cytochrome P450 aromatase (CYP19; EC1.14.14.1), and their selectivity relative to another enzyme of the P450 family. A satisfactory agreement between experimental and predicted data allowed us to assert that a properly built "enantioselective CoMFA model" might constitute a useful tool for addressing enantioselective ligands design.

  DOI：

  10.1021/jm058042r

文献信息

• Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach
  作者：Andrea Cavalli、Alessandra Bisi、Carlo Bertucci、Carlo Rosini、Anja Paluszcak、Silvia Gobbi、Egidio Giorgio、Angela Rampa、Federica Belluti、Lorna Piazzi、Piero Valenti、Rolf W. Hartmann、Maurizio Recanatini

  DOI：10.1021/jm058042r

  日期：2005.11.1

  To identify enantioselective nonsteroidal aromatase inhibitors, a multidisciplinary medicinal chemistry approach was pursued. First, our earlier CoMFA model [Bioorg. Med. Chem. 1998, 6, 377-3881 was extended taking purposely into account previously discovered enantioselective aromatase inhibitors. The 3D QSAR model was then exploited to design chiral ligands, whose configurational assignment was obtained, after HPLC separation, by means of a combination of circular dichroism measurements and time dependent density functional calculations. Finally, the new enantiomeric inhibitors were separately tested to ascertain both their potency against the cytochrome P450 aromatase (CYP19; EC1.14.14.1), and their selectivity relative to another enzyme of the P450 family. A satisfactory agreement between experimental and predicted data allowed us to assert that a properly built "enantioselective CoMFA model" might constitute a useful tool for addressing enantioselective ligands design.