N-benzoyl-5-(2-nitrophenyl)-3-phenyl-4,5-dihydro-2-pyrazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzoyl-5-(2-nitrophenyl)-3-phenyl-4,5-dihydro-2-pyrazoline
• 英文别名: N-benzoyl-5-(2’-nitrophenyl)-3-phenyl-2-pyrazoline；1-benzoyl-3-phenyl-5-(2-nitrophenyl)-2-pyrazoline；[5-(2-nitrophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl](phenyl)methanone；[3-(2-nitrophenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-phenylmethanone
• 化学式: C₂₂H₁₇N₃O₃
• 分子量: 371.395
• InChiKey: OZHCSTRHRJNZPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-nitrochalcone 在 一水合肼 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 0.67h， 生成 N-benzoyl-5-(2-nitrophenyl)-3-phenyl-4,5-dihydro-2-pyrazoline
  参考文献：
  名称：

  Pyrazolines ? Derivatives of 2-nitrochalcone

  摘要：

  DOI：

  10.1007/bf00531506

文献信息

• N-formylpyrazolines and N-benzoylpyrazolines as novel inhibitors of mammalian cathepsin B and cathepsin H
  作者：N. Raghav、S. Garg

  DOI：10.1016/j.bioorg.2014.07.012

  日期：2014.12

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes ranging from degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis, etc. High levels of cathepsins have been indicated in various pathological conditions like arthritis, cancer and other tissue degenerative disorders. One of the reasons attributed to these high levels is decrease in inhibitor concentration. Therefore, the work on the identification of small molecular weight compounds as inhibitors of cysteine proteases is of great therapeutic significance. Exploring this work in the same direction, we here present the synthesis of substituted N-formylpyrazolines and N-benzoylpyrazolines and study these as inhibitors to cysteine proteases. After a preliminary screening of the compounds as inhibitors to cysteine proteases in general, studies were carried out to study their inhibitory effects on cathepsin B and cathepsin H. SAR studies show that N-formylpyrazolines were better inhibitors than N-benzoylpyrazolines. The most potent inhibitors among the two series were nitro substituted compounds 1i and 2i with K-i values of similar to 1.1 x 10 (9) M and 19.5 x 10 (8) M for cathepsin B and K-i values of similar to 5.19 x 10 (8) M and 9.8 x 10 (7) M for cathepsin H, respectively. Docking experiments showing interaction between N-formylpyrazolines and N-benzoylpyrazolines with enzyme active sites structures also provided useful insights. (C) 2014 Elsevier Inc. All rights reserved.
• Pyrazolines ? Derivatives of 2-nitrochalcone
  作者：V. D. Orlov、N. V. Getmanskii、O. V. Shishkin、E. E. Lakin、V. P. Kuznetsov

  DOI：10.1007/bf00531506

  日期：1993.3