4-氨基-1-苯基-1,2-二氢吡唑-3-酮 | 7409-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-1-苯基-1,2-二氢吡唑-3-酮
• 英文名称: 1-Phenyl-4-amino-3-hydroxy-pyrazol
• 英文别名: 4-amino-1-phenyl-1,2-dihydro-pyrazol-3-one；4-Amino-1-phenyl-1,2-dihydro-pyrazol-3-on；4-amino-2-phenyl-1H-pyrazol-5-one
• CAS: 7409-23-6
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: YXPBYEQVYCJPKR-UHFFFAOYSA-N

物化性质

• 熔点：
  198-201 °C
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴-2-氯乙酰苯胺 、 4-氨基-1-苯基-1,2-二氢吡唑-3-酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以23%的产率得到2-(4-amino-5-oxo-2-phenyl-2,5-dihydropyrazol-1-yl)-N-(4-bromophenyl)acetamide
  参考文献：
  名称：

  新型吡唑和吡唑酮衍生物作为 N-甲酰肽受体激动剂的合成、生物学评价、分子建模和结构分析

  摘要：

  N-甲酰肽受体（FPR1、FPR2 和 FPR3）在炎症过程的调节中起关键作用，最近证明 FPR1 和 FPR2 在某些癌症的进展/抑制中具有双重作用。因此，FPR 代表了治疗癌症和炎性疾病的重要治疗靶点。以前，我们确定了选择性或混合 FPR 激动剂与哒嗪酮或吡啶酮支架显示常见的 4-（溴苯基）乙酰胺片段，这对活性至关重要。我们在此报告新的吡唑和吡唑啉酮衍生物作为上述 6 元化合物的受限类似物，均具有相同的 4-溴苯乙酰胺侧链。大多数新产品的 FPR 激动剂活性较低或不存在，这表明吡唑核不适用于 FPR 激动剂。

  DOI：

  10.1111/cbdd.13913
• 作为产物：
  描述：

  4-硝基-1-苯基-1,2-二氢吡唑-3-酮 在 palladium on activated charcoal 氢气 作用下， 生成 4-氨基-1-苯基-1,2-二氢吡唑-3-酮
  参考文献：
  名称：

  Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors

  摘要：

  A new series of potential human 5-LOX inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 2) has been synthesized and the activity against COX-1, COX-2, and human 5-LOX enzymes has been evaluated. In contrast with literature data, we observed that phenidone resulted to be inactive against human 5-LOX, while retains its activity against cyclooxygenases in a micromolar range. The present results suggest that the substitution of the amino function at the 4-position is detrimental in terms of activity toward COX-1 and COX-2, while the presence of a double bond at the 4,5-position does not alter the biological profile against COX. The absence of activity vs. human 5-LOX strongly suggests a re-consideration of phenidone and its analogs as 5-LOX inhibitors in humans.

  DOI：

  10.1016/j.farmac.2004.09.002

文献信息

• Kuemmell; Remy, Zeitschrift fur Elektrochemie und angewandte physikalische Chemie, 1909, vol. 15, p. 254
  作者：Kuemmell、Remy

  DOI：——

  日期：——
• US3933886A
  申请人：——

  公开号：US3933886A

  公开（公告）日：1976-01-20
• Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors
  作者：Claudia Cusan、Giampiero Spalluto、Maurizio Prato、Michael Adams、Antje Bodensieck、Rudolf Bauer、Aurelia Tubaro、Paolo Bernardi、Tatiana Da Ros

  DOI：10.1016/j.farmac.2004.09.002

  日期：2005.1

  A new series of potential human 5-LOX inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 2) has been synthesized and the activity against COX-1, COX-2, and human 5-LOX enzymes has been evaluated. In contrast with literature data, we observed that phenidone resulted to be inactive against human 5-LOX, while retains its activity against cyclooxygenases in a micromolar range. The present results suggest that the substitution of the amino function at the 4-position is detrimental in terms of activity toward COX-1 and COX-2, while the presence of a double bond at the 4,5-position does not alter the biological profile against COX. The absence of activity vs. human 5-LOX strongly suggests a re-consideration of phenidone and its analogs as 5-LOX inhibitors in humans.
• Synthesis, biological evaluation, molecular modeling, and structural analysis of new pyrazole and pyrazolone derivatives as N‐formyl peptide receptors agonists
  作者：Claudia Vergelli、Andrei I. Khlebnikov、Letizia Crocetti、Gabriella Guerrini、Niccolò Cantini、Liliya N. Kirpotina、Igor A. Schepetkin、Agostino Cilibrizzi、Mark T. Quinn、Patrizia Rossi、Paola Paoli、Maria Paola Giovannoni

  DOI：10.1111/cbdd.13913

  日期：2021.10

  fragment, which was essential for activity. We report here new pyrazole and pyrazolone derivatives as restricted analogues of the above 6-membered compounds, all exhibiting the same 4-bromophenylacetamide side chain. Most new products had low or absent FPR agonist activity, suggesting that the pyrazole nucleus was not appropriate for FPR agonists. This hypothesis was confirmed by molecular modeling studies

  N-甲酰肽受体（FPR1、FPR2 和 FPR3）在炎症过程的调节中起关键作用，最近证明 FPR1 和 FPR2 在某些癌症的进展/抑制中具有双重作用。因此，FPR 代表了治疗癌症和炎性疾病的重要治疗靶点。以前，我们确定了选择性或混合 FPR 激动剂与哒嗪酮或吡啶酮支架显示常见的 4-（溴苯基）乙酰胺片段，这对活性至关重要。我们在此报告新的吡唑和吡唑啉酮衍生物作为上述 6 元化合物的受限类似物，均具有相同的 4-溴苯乙酰胺侧链。大多数新产品的 FPR 激动剂活性较低或不存在，这表明吡唑核不适用于 FPR 激动剂。