N-(1-naphthyl)-2-phenyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carboxamide | 1355577-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-naphthyl)-2-phenyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carboxamide
• 英文别名: N-naphthalen-1-yl-2-phenyl-2,3-dihydroimidazo[1,2-b]pyrazole-1-carboxamide
• CAS: 1355577-23-9
• 化学式: C₂₂H₁₈N₄O
• 分子量: 354.411
• InChiKey: XKTHEPODZBBFQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydrazino-1-phenylethanol 在 硫酸 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.25h， 生成 N-(1-naphthyl)-2-phenyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carboxamide
  参考文献：
  名称：

  N-Aryl-2-phenyl-2,3-dihydro-imidazo[1,2-b]pyrazole-1-carboxamides 7-substituted strongly inhibiting both fMLP-OMe- and IL-8-induced human neutrophil chemotaxis

  摘要：

  Anomalous activation of neutrophil recruitment is one of the causes of many inflammatory diseases. The chemoattractants N-formyl-methionyl-leucyl-phenylalanine (fMLP), and interleukine 8 (IL8) play a pivotal role in neutrophil chemotaxis regulation in the latter and early stages, respectively, probably by two independent mechanisms. We reported here synthesis and biological evaluation of new N-aryl-2-pheny1-2,3-dihydro-imidazo[1,2-b]pyrazole-1-carboxamides 7-substituted which were designed as possible multi-target antiinflammatory agents. Many of the title compounds showed a good inhibition, in the nano molar range, of human neutrophil chemotaxis selectively acting toward fMLP-OMe (methylester of fMLP) or IL8 stimulus; whereas, two compounds showed an interesting dual activity inhibiting both fMLP-OMe and IL8-induced chemotaxis at nano molar concentration. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.031

文献信息

• N-Aryl-2-phenyl-2,3-dihydro-imidazo[1,2-b]pyrazole-1-carboxamides 7-substituted strongly inhibiting both fMLP-OMe- and IL-8-induced human neutrophil chemotaxis
  作者：Chiara Brullo、Susanna Spisani、Rita Selvatici、Olga Bruno

  DOI：10.1016/j.ejmech.2011.11.031

  日期：2012.1

  Anomalous activation of neutrophil recruitment is one of the causes of many inflammatory diseases. The chemoattractants N-formyl-methionyl-leucyl-phenylalanine (fMLP), and interleukine 8 (IL8) play a pivotal role in neutrophil chemotaxis regulation in the latter and early stages, respectively, probably by two independent mechanisms. We reported here synthesis and biological evaluation of new N-aryl-2-pheny1-2,3-dihydro-imidazo[1,2-b]pyrazole-1-carboxamides 7-substituted which were designed as possible multi-target antiinflammatory agents. Many of the title compounds showed a good inhibition, in the nano molar range, of human neutrophil chemotaxis selectively acting toward fMLP-OMe (methylester of fMLP) or IL8 stimulus; whereas, two compounds showed an interesting dual activity inhibiting both fMLP-OMe and IL8-induced chemotaxis at nano molar concentration. (C) 2011 Elsevier Masson SAS. All rights reserved.