DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole | 33722-47-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
• 英文别名: (cis)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole；(+/-)-1-benzyl-2,4r,5c-triphenyl-4,5-dihydro-1H-imidazole；(+/-)-1-Benzyl-2,4r,5c-triphenyl-4,5-dihydro-1H-imidazol；(4S,5R)-1-benzyl-2,4,5-triphenyl-4,5-dihydroimidazole
• CAS: 33722-47-3
• 化学式: C₂₈H₂₄N₂
• 分子量: 388.512
• InChiKey: VSOVRPJUEZLLSA-RRPNLBNLSA-N

物化性质

• 沸点：
  549.3±60.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴甲苯 、 cis-2,4,5-triphenyl-2-imidazoline 在 三乙胺 作用下， 以 苯 为溶剂， 反应 15.0h， 以20%的产率得到DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds

  摘要：

  The mammalian nuclear transcription factor NF-kappa B is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-alpha) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-kappa B has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-kappa B mediated gene transcription in cell culture as well as inhibitors of TNF-alpha and IL-6 production in interleukin 1 beta (IL-1 beta) stimulated human blood.

  DOI：

  10.1021/jm8013162

文献信息

• Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
  作者：Boran Xu、Kraig Worrall、Bruce Arndtsen

  DOI：10.3390/molecules171213759

  日期：——

  We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl(3) is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates

  我们描述了钯催化的 2-咪唑啉多组分合成。该反应通过亚胺、酰氯和一氧化碳的偶联进行，形成咪唑啉羧酸盐，然后脱羧。发现在 CHCl(3) 中脱羧会产生咪唑啉鎓和咪唑鎓盐的混合物。然而，苯甲酸的加入抑制了芳构化，并以良好的产率生成了反式二取代的咪唑啉。将此反应与随后的氮脱保护相结合，可以从多个可用的结构单元中全面合成咪唑啉。
• Claus; Elbs, Chemische Berichte, 1883, vol. 16, p. 1272
  作者：Claus、Elbs

  DOI：——

  日期：——
• Claus; Kohlstock, Chemische Berichte, <hi>1885</hi>, vol. 18, p. 1855
  作者：Claus、Kohlstock

  DOI：——

  日期：——
• Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds
  作者：Daljinder K. Kahlon、Theresa A. Lansdell、Jason S. Fisk、Christopher D. Hupp、Timothy L. Friebe、Stacy Hovde、A. Daniel Jones、Richard D. Dyer、R. William Henry、Jetze J. Tepe

  DOI：10.1021/jm8013162

  日期：2009.3.12

  The mammalian nuclear transcription factor NF-kappa B is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-alpha) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-kappa B has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-kappa B mediated gene transcription in cell culture as well as inhibitors of TNF-alpha and IL-6 production in interleukin 1 beta (IL-1 beta) stimulated human blood.