N-(4-(trifluoromethoxy)phenyl)-1H-indazole-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(trifluoromethoxy)phenyl)-1H-indazole-3-carboxamide
• 英文别名: N-[4-(trifluoromethoxy)phenyl]-1H-indazole-3-carboxamide
• 化学式: C₁₅H₁₀F₃N₃O₂
• 分子量: 321.259
• InChiKey: AMOPLFALXGESBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对三氟甲氧基苯胺 、 吲唑-3-羧酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到N-(4-(trifluoromethoxy)phenyl)-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis

  摘要：

  We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of alpha-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified 3k and 6g as lead compounds which displayed almost 5 and 9 times more potent inhibition of alpha-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R-3) for the compounds (3a-p) and presence of +M group at ortho position (R-5) for the compounds (6a-j) were crucial for their excellent inhibition activities of alpha-MSH-stimulated melanogenesis.

  DOI：

  10.1016/j.bmcl.2019.07.055

文献信息

• Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis
  作者：Sateesh Kumar Arepalli、Chaerim Lee、Jae-Kyung Jung、Youngsoo Kim、Kiho Lee、Heesoon Lee

  DOI：10.1016/j.bmcl.2019.07.055

  日期：2019.9

  We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of alpha-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified 3k and 6g as lead compounds which displayed almost 5 and 9 times more potent inhibition of alpha-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R-3) for the compounds (3a-p) and presence of +M group at ortho position (R-5) for the compounds (6a-j) were crucial for their excellent inhibition activities of alpha-MSH-stimulated melanogenesis.