4-(3-甲基-4-氧代-4H-苯并吡喃-2-基)苯甲腈 | 775315-38-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 4-(3-甲基-4-氧代-4H-苯并吡喃-2-基)苯甲腈
• 中文别名: 苯甲腈,4-(3-甲基-4-羰基-4H-1-苯并吡喃-2-基)-
• 英文名称: 4'-cyano-3-methylflavone
• 英文别名: 4-(3-Methyl-4-oxo-4H-chromen-2-yl)benzonitrile；4-(3-methyl-4-oxochromen-2-yl)benzonitrile
• CAS: 775315-38-3
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: WHNAEROJXWYKEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-甲基-4-氧代-4H-苯并吡喃-2-基)苯甲腈 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， 反应 5.0h， 生成 3-(bromomethyl)-4'-cyanoflavone
  参考文献：
  名称：

  Lead Optimization Providing a Series of Flavone Derivatives as Potent Nonsteroidal Inhibitors of the Cytochrome P450 Aromatase Enzyme

  摘要：

  Following our SAR studies on aromatase inhibitors, new compounds were designed by appropriately modifying the structure of flavone 1 using our previously reported CoMFA model. While the introduction of substituents on the 2-phenyl ring alone did not cause improvement in potency, these modifications and the removal of the 7-methoxy group led to compounds showing inhibitory activity in the nanomolar range, comparable to the marketed drug fadrozole.

  DOI：

  10.1021/jm060186y
• 作为产物：
  描述：

  2'-羟基苯丙酮 、 对氰基苯甲酰氯 在 sodium 4-cyanobenzoate 作用下， 反应 7.0h， 以34%的产率得到4-(3-甲基-4-氧代-4H-苯并吡喃-2-基)苯甲腈
  参考文献：
  名称：

  Lead Optimization Providing a Series of Flavone Derivatives as Potent Nonsteroidal Inhibitors of the Cytochrome P450 Aromatase Enzyme

  摘要：

  Following our SAR studies on aromatase inhibitors, new compounds were designed by appropriately modifying the structure of flavone 1 using our previously reported CoMFA model. While the introduction of substituents on the 2-phenyl ring alone did not cause improvement in potency, these modifications and the removal of the 7-methoxy group led to compounds showing inhibitory activity in the nanomolar range, comparable to the marketed drug fadrozole.

  DOI：

  10.1021/jm060186y

文献信息

• Lead Optimization Providing a Series of Flavone Derivatives as Potent Nonsteroidal Inhibitors of the Cytochrome P450 Aromatase Enzyme
  作者：Silvia Gobbi、Andrea Cavalli、Angela Rampa、Federica Belluti、Lorna Piazzi、Anja Paluszcak、Rolf W. Hartmann、Maurizio Recanatini、Alessandra Bisi

  DOI：10.1021/jm060186y

  日期：2006.7.1

  Following our SAR studies on aromatase inhibitors, new compounds were designed by appropriately modifying the structure of flavone 1 using our previously reported CoMFA model. While the introduction of substituents on the 2-phenyl ring alone did not cause improvement in potency, these modifications and the removal of the 7-methoxy group led to compounds showing inhibitory activity in the nanomolar range, comparable to the marketed drug fadrozole.