(S)-(-)-2-(methylbenzyl)amino-2-oxo-N-[4-cyano-1-phenyl-1H-pyrazol-5-yl]acetamide | 1245747-37-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(-)-2-(methylbenzyl)amino-2-oxo-N-[4-cyano-1-phenyl-1H-pyrazol-5-yl]acetamide
• 英文别名: N-(4-cyano-2-phenylpyrazol-3-yl)-N'-[(1S)-1-phenylethyl]oxamide
• CAS: 1245747-37-8
• 化学式: C₂₀H₁₇N₅O₂
• 分子量: 359.387
• InChiKey: XFUHWXLDEBWWJK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N1,N2-bis(4-cyano-1-phenyl-1H-pyrazol-5-yl)oxalamide 、 (S)-(-)- α-甲基苄胺 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到(S)-(-)-2-(methylbenzyl)amino-2-oxo-N-[4-cyano-1-phenyl-1H-pyrazol-5-yl]acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazole compounds

  摘要：

  A novel dipyrazole ethandiamide compound and acid chloride of pyrazolo[3,4-d] pyrimidine 4(5H)-one were prepared and reacted with a number of nucleophiles. The resultant novel compounds were tested in several in vitro and in vivo assays. Three compounds inhibited the secretion of neurotoxins by human THP-1 monocytic cells at concentrations that were not toxic to these cells. They also partially inhibited both cyclooxygenase-1 and -2 isoforms. In animal studies, two compounds were notable for their anti-inflammatory activity that was comparable to that of the clinically available cyclooxygenase-2 inhibitor celecoxib. Modeling studies by using the molecular operating environment module showed comparable docking scores for the two enantiomers docked in the active site of cyclooxygenase-2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.018

文献信息

• Synthesis and biological evaluation of novel pyrazole compounds
  作者：Amal M. Youssef、Edward G. Neeland、Erika B. Villanueva、M. Sydney White、Ibrahim M. El-Ashmawy、Brian Patrick、Andis Klegeris、Alaa S. Abd-El-Aziz

  DOI：10.1016/j.bmc.2010.06.018

  日期：2010.8

  A novel dipyrazole ethandiamide compound and acid chloride of pyrazolo[3,4-d] pyrimidine 4(5H)-one were prepared and reacted with a number of nucleophiles. The resultant novel compounds were tested in several in vitro and in vivo assays. Three compounds inhibited the secretion of neurotoxins by human THP-1 monocytic cells at concentrations that were not toxic to these cells. They also partially inhibited both cyclooxygenase-1 and -2 isoforms. In animal studies, two compounds were notable for their anti-inflammatory activity that was comparable to that of the clinically available cyclooxygenase-2 inhibitor celecoxib. Modeling studies by using the molecular operating environment module showed comparable docking scores for the two enantiomers docked in the active site of cyclooxygenase-2. (C) 2010 Elsevier Ltd. All rights reserved.