8-bromo-6-chloro-2-(3-methoxy-2-nitrophenyl)chromone | 1621457-83-7

• 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: 8-bromo-6-chloro-2-(3-methoxy-2-nitrophenyl)chromone
• CAS: 1621457-83-7
• 化学式: C₁₆H₉BrClNO₅
• 分子量: 410.608
• InChiKey: PFCXZOFPJSXOTO-UHFFFAOYSA-N

物化性质

• 沸点：
  578.1±50.0 °C(Predicted)
• 密度：
  1.687±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.58
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-2-(3-methoxy-2-nitrophenyl)chromone 在 盐酸 、 tin 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 生成 2-(2-amino-3-methoxyphenyl)-8-(benzylamino)-6-chloro-4H-chromen-4-one
  参考文献：
  名称：

  Towards the development of chromone-based MEK1/2 modulators

  摘要：

  Inhibition or allosteric modulation of mitogen-activated protein kinase kinases MEK1 and MEK2 (MEK1/2) represent a promising strategy for the discovery of new specific anticancer agents. In this paper, structure-based design, beginning from the lead compound PD98059, was used to study potential structural modifications on the chromone structure in order to obtain highly potent derivatives that target the allosteric pocket in MEK1. Subsequently, a small series of PD98059 analogs were synthesized to provide a first generation of chromone-based derivatives that inhibit the activation of MEK1 with IC50 values as low as 30 nM in vitro. Complementary cellular studies also showed that two of the compounds in the series inhibit the activity of MEK1/2 with IC50 values in the nanomolar range (73-97 nM). In addition, compounds in this series were found to inhibit the proliferation of a small panel of human cancer cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.018
• 作为产物：
  描述：

  2-acetyl-6-bromo-4-chlorophenyl 3-methoxy-2-nitrobenzoate 在 硫酸 、 potassium hydroxide 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 1.0h， 生成 8-bromo-6-chloro-2-(3-methoxy-2-nitrophenyl)chromone
  参考文献：
  名称：

  Towards the development of chromone-based MEK1/2 modulators

  摘要：

  Inhibition or allosteric modulation of mitogen-activated protein kinase kinases MEK1 and MEK2 (MEK1/2) represent a promising strategy for the discovery of new specific anticancer agents. In this paper, structure-based design, beginning from the lead compound PD98059, was used to study potential structural modifications on the chromone structure in order to obtain highly potent derivatives that target the allosteric pocket in MEK1. Subsequently, a small series of PD98059 analogs were synthesized to provide a first generation of chromone-based derivatives that inhibit the activation of MEK1 with IC50 values as low as 30 nM in vitro. Complementary cellular studies also showed that two of the compounds in the series inhibit the activity of MEK1/2 with IC50 values in the nanomolar range (73-97 nM). In addition, compounds in this series were found to inhibit the proliferation of a small panel of human cancer cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.018