4'-bromo-3-methylflavone | 905601-22-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4'-bromo-3-methylflavone
• 英文别名: 3-methyl-2-(4'-bromophenyl)-4H-benzopyran-4-one；2-(4-bromophenyl)-3-methyl-4H-chromen-4-one；2-(4-Bromophenyl)-3-methylchromen-4-one
• CAS: 905601-22-1
• 化学式: C₁₆H₁₁BrO₂
• 分子量: 315.166
• InChiKey: ITTLFOBZASCCRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-bromo-3-methylflavone 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 4'-bromo-3-(bromomethyl)flavone
  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：

  4-Brom-α-methyl-2'-hydroxy-chalkon 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到4'-bromo-3-methylflavone
  参考文献：
  名称：

  Jayashree; Alam, Afroze; Kumar, D. Vijay, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 237 - 240

  摘要：

  DOI：

文献信息

• Synthesis of 3-methylflavones and their antioxidant and antibacterial activities
  作者：B. S. Jayashree、Afroze Alam、Yogendra Nayak、D. Vijay Kumar

  DOI：10.1007/s00044-011-9725-y

  日期：2012.8

  An attempt was made to synthesise newer 3-methylflavones with various substitution on the ring A and B of 2-phenylchromen-4-one. They were evaluated for antioxidant activity and antibacterial activity against the Gram-positive and Gram-negative bacteria. Five test compounds exhibited DPPH radical scavenging activity with IC50 below 100 mu g/ml, and the same test compounds exhibited 50-100% growth inhibition in Gram-positive bacteria against standard Amoxicillin.
• Synthesis of functionalized flavones from 3-halo-2-(methylthio)-4H-chromen-4-ones
  作者：Amr Elagamy、Laila K. Elghoneimy、Reem K. Arafa、Ramendra Pratap

  DOI：10.1016/j.tetlet.2022.153882

  日期：2022.6

  A simple and efficient method for the synthesis of flavones was achieved by selective sulfide Liebeskind-Srogl cross-coupling reaction of 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones with arylboronic acids. This method is the first example of employing Liebeskind-Srogl coupling for the synthesis of flavones. Various aryl groups can be directly installed to the chromone