1-cyclobutanecarbonyl-3-(5-methoxy-2-nitrophenyl)-4,5-dihydro-1H-pyrazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-cyclobutanecarbonyl-3-(5-methoxy-2-nitrophenyl)-4,5-dihydro-1H-pyrazole
• 英文别名: Cyclobutyl-[5-(5-methoxy-2-nitrophenyl)-3,4-dihydropyrazol-2-yl]methanone
• 化学式: C₁₅H₁₇N₃O₄
• 分子量: 303.318
• InChiKey: XXUFACPOQVGOSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-cyclobutanecarbonyl-3-(5-methoxy-2-nitrophenyl)-4,5-dihydro-1H-pyrazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 [5-(2-Amino-5-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-cyclobutylmethanone
  参考文献：
  名称：

  4,5-Dihydro-1H-pyrazole Derivatives with Inhibitory nNOS Activity in Rat Brain:  Synthesis and Structure−Activity Relationships

  摘要：

  In an attempt to find new compounds with neuroprotective activity, we have designed, synthesized and characterized 19 new nNOS inhibitors with a 4,5-dihydro-1H-pyrazole structure. Compounds 11r [1-cyclopropanecarbonyl-3-(2-amino-5-chlorophenyl)-4,5-dihydro-1H-pyrazole] and He [1-cyclopropanecarbonyl-3-(2-amino-5-methoxyphenyl)- 4,5-dihydro-1H-pyrazole] show the highest activities with inhibition percentages of 70% and 62%, respectively. A structure-activity relationship for the nNOS inhibition can be established from the structural comparison of these new pyrazole derivatives and the described synthetic kynurenines 10.

  DOI：

  10.1021/jm0407714
• 作为产物：
  描述：

  5-methoxy-2-nitrophenyl vinyl ketone 、 环丁基甲酰氯 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以82%的产率得到1-cyclobutanecarbonyl-3-(5-methoxy-2-nitrophenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  4,5-Dihydro-1H-pyrazole Derivatives with Inhibitory nNOS Activity in Rat Brain:  Synthesis and Structure−Activity Relationships

  摘要：

  In an attempt to find new compounds with neuroprotective activity, we have designed, synthesized and characterized 19 new nNOS inhibitors with a 4,5-dihydro-1H-pyrazole structure. Compounds 11r [1-cyclopropanecarbonyl-3-(2-amino-5-chlorophenyl)-4,5-dihydro-1H-pyrazole] and He [1-cyclopropanecarbonyl-3-(2-amino-5-methoxyphenyl)- 4,5-dihydro-1H-pyrazole] show the highest activities with inhibition percentages of 70% and 62%, respectively. A structure-activity relationship for the nNOS inhibition can be established from the structural comparison of these new pyrazole derivatives and the described synthetic kynurenines 10.

  DOI：

  10.1021/jm0407714