5-(3-Amino-phenylethynyl)-2-ureido-thiophene-3-carboxylic acid amide | 859809-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(3-Amino-phenylethynyl)-2-ureido-thiophene-3-carboxylic acid amide
• 英文别名: 5-[2-(3-Aminophenyl)ethynyl]-2-(carbamoylamino)thiophene-3-carboxamide
• CAS: 859809-34-0
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: XXEASVYOHKGAAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Amino-phenylethynyl)-2-ureido-thiophene-3-carboxylic acid amide 、 N,N-二甲基甘氨酸 在 二甲基十二/十四烷基叔胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-[3-(2-Dimethylamino-acetylamino)-phenylethynyl]-2-ureido-thiophene-3-carboxylic acid amide
  参考文献：
  名称：

  Inhibition of IKK-2 by 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides

  摘要：

  A series of 21 novel 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides were synthesized and evaluated for the inhibition of IKK-2. In spite of their often modest activity on the enzyme, six selected analogs showed significant inhibition of the production of inflammatory cytokine IL-8 in IL-1 beta stimulated rheumatoid arthritis-derived synovial fibroblasts, demonstrating their potential usefulness as NF-kappa B regulators. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.090
• 作为产物：
  描述：

  2-[(氨基羰基)氨基]-5-溴-3-噻吩羧酰胺 、 3-氨基苯乙炔 在 N,N-二异丙基乙胺 copper(l) iodide 、 二(氰基苯)二氯化钯 、 (i-Pr₂)2Fc 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 以17%的产率得到5-(3-Amino-phenylethynyl)-2-ureido-thiophene-3-carboxylic acid amide
  参考文献：
  名称：

  Inhibition of IKK-2 by 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides

  摘要：

  A series of 21 novel 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides were synthesized and evaluated for the inhibition of IKK-2. In spite of their often modest activity on the enzyme, six selected analogs showed significant inhibition of the production of inflammatory cytokine IL-8 in IL-1 beta stimulated rheumatoid arthritis-derived synovial fibroblasts, demonstrating their potential usefulness as NF-kappa B regulators. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.090