7-hydroxy-3-methyl-4'-nitroflavone | 1094-30-0

• 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: 7-hydroxy-3-methyl-4'-nitroflavone
• 英文别名: 7-Hydroxy-3-methyl-4'-nitroflavon；7-hydroxy-3-methyl-2-(4-nitro-phenyl)-chromen-4-one；4h-1-Benzopyran-4-one,7-hydroxy-3-methyl-2-(4-nitrophenyl)-；7-hydroxy-3-methyl-2-(4-nitrophenyl)chromen-4-one
• CAS: 1094-30-0
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: ACRHPNNURHUXMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 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：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-methyl-4'-nitroflavone 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 12.0h， 生成 3-(bromomethyl)-7-methoxy-4'-nitroflavone
  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：

  2,4-二羟基苯丙酮 、 4-硝基苯甲酰氯 在 4-硝基苯甲酸钠 作用下， 反应 7.0h， 以70%的产率得到7-hydroxy-3-methyl-4'-nitroflavone
  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

• Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents
  作者：Yerrabelly Jayaprakash Rao、Thummala Sowjanya、Gogula Thirupathi、Nandula Yadagiri Sreenivasa Murthy、Sudha Sravanti Kotapalli

  DOI：10.1007/s11030-018-9833-4

  日期：2018.11

  AbstractA series of new flavone/isoxazole fused heterocycles 5a–f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a–t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial

  摘要通过分子内环化和Cu（I）催化的点击1,3-偶极环加成反应合成了一系列新的黄酮/异恶唑稠合杂环5a-f和黄酮/ 1,2,3-三唑/苯并咪唑杂合杂环化合物7a-t。使用磺基罗丹明B测定（SRB）评估了产品对人乳腺癌细胞系（MCF-7）的抗增殖活性，并使用浊度测定法评估了产品的抗分枝杆菌活性。大多数测试化合物显示出抗增殖活性和抗分枝杆菌活性。化合物7l，7q和7r显示出中等的抗增殖活性，IC50值为 17.9、14.2、19.1（\ upmu \ hbox M} \）分别地，化合物5a和化合物5a在30 （\ upmu \ hbox M} \）浓度下显示出中等的抗分枝杆菌活性，抑制率为41.7％  。 图形概要