1-(3,4-dimethylphenyl)-5-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester | 374924-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,4-dimethylphenyl)-5-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(3,4-dimethylphenyl)-3-oxo-1H-pyrazole-4-carboxylate
• CAS: 374924-92-2
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: UUTKKOIXWTYVNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethylphenyl)-5-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester 在 10percent aq. NaOH 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到2-(3,4-dimethylphenyl)-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 、 3,4-二甲基苯肼盐酸盐 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以89%的产率得到1-(3,4-dimethylphenyl)-5-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l