N-(4-hydroxyphenyl)-1H-indazole-3-carboxamide | 862248-39-3

• 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-hydroxyphenyl)-1H-indazole-3-carboxamide
• 英文别名: 1H-indazole-3-carboxylic acid (4-hydroxy-phenyl)-amide
• CAS: 862248-39-3；1042593-39-4
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: KQEOYRPEVYBIQW-UHFFFAOYSA-N

物化性质

• 沸点：
  430.8±25.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氨基苯酚 、 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41%的产率得到N-(4-hydroxyphenyl)-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

• Hetero-substituted acetanilide derivatives as analgesic agents
  申请人：Carson R. John

  公开号：US20050182108A1

  公开（公告）日：2005-08-18

  Hetero-substituted acetanilide derivatives are disclosed as analgesic agents. The compounds of the invention are useful in methods for treating a disease or condition in a mammal characterized by pain and/or fever.

  本发明公开了异取代乙酰苯胺衍生物作为镇痛剂的化合物。该发明的化合物在治疗哺乳动物因疼痛和/或发热而表现出的疾病或症状的方法中是有用的。
• HETERO-SUBSTITUTED ACETANILIDE DERIVATIVES AS ANALGESIC AGENTS
  申请人：Carson John R.

  公开号：US20100204284A1

  公开（公告）日：2010-08-12

  Hetero-substituted acetanilide derivatives are disclosed as analgesic agents. The compounds of the invention are useful in methods for treating a disease or condition in a mammal characterized by pain and/or fever.

  本发明揭示了杂代替醋酰苯胺衍生物作为镇痛剂。该发明的化合物在治疗哺乳动物的疾病或状况中具有用途，其特征为疼痛和/或发热。
• Hetero-Substituted Acetanilide Derivatives As Analgesic Agents
  申请人：Janssen Pharmaceutica N.V

  公开号：US20150209339A1

  公开（公告）日：2015-07-30

  Hetero-substituted acetanilide derivatives are disclosed as analgesic agents. The compounds of the invention are useful in methods for treating a disease or condition in a mammal characterized by pain and/or fever.

  本发明揭示了杂代替乙酰苯胺衍生物作为镇痛剂。本发明的化合物适用于治疗哺乳动物中由疼痛和/或发热所特征的疾病或症状的方法。
• 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.