4-(4-((2-(4-(6-bromo-2-oxo-2H-chromen-3-yl)thiazol-2-yl)hydrazineylidene)methyl)-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide | 1620485-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-((2-(4-(6-bromo-2-oxo-2H-chromen-3-yl)thiazol-2-yl)hydrazineylidene)methyl)-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide
• CAS: 1620485-97-3
• 化学式: C₂₈H₁₉BrN₆O₄S₂
• 分子量: 647.533
• InChiKey: RALXQSUJFFLQBR-UHFFFAOYSA-N

物化性质

• 熔点：
  336-338 °C
• 沸点：
  882.8±75.0 °C(predicted)
• 密度：
  1.66±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  145.47
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-({1-[4-(aminosulfonyl)phenyl]-3-phenyl-1H-pyrazol-4-yl}methylidene)-1-hydrazinecarbothioamide 、 6-bromo-3-(2-bromoacetyl)-2H-chromen-2-one 在 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 4-(4-((2-(4-(6-bromo-2-oxo-2H-chromen-3-yl)thiazol-2-yl)hydrazineylidene)methyl)-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Dual evaluation of some novel 2-amino-substituted coumarinylthiazoles as anti-inflammatory–antimicrobial agents and their docking studies with COX-1/COX-2 active sites

  摘要：

  Synthesis of total eighteen 2-amino-substituted 4-coumarinylthiazoles including sixteen new compounds (3a-o and 5b) bearing the benzenesulfonamide moiety is described in the present report. All the synthesized target compounds were examined for their in vivo anti-inflammatory (AI) activity and in vitro antimicrobial activity. Results revealed that six compounds (3d, 3f, 3g, 3h, 3j and 3n) exhibited pronounced anti-inflammatory activity comparable to the standard drug indomethacin. AI results were further confirmed by the docking studies of the most active (3n) and the least active compound (3a) with COX-1 and COX-2 active sites. In addition, most of the compounds exhibited moderate antimicrobial activity against Gram-positive bacteria as well as fungal yeast, S. cervisiae. Comparison between 3 and 5 indicated that incorporation of additional substituted pyrazole nucleus into the scaffold significantly enhanced AI activity.

  DOI：

  10.3109/14756366.2013.805755