4-diazo-1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-diazo-1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one
• 英文别名: 4-Diazonio-2-(3,4-dimethylphenyl)-5-methylpyrazol-3-olate
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: NJHYMMGAIBGUTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-diazo-1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one 生成 4-{[1-(3,4-Dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]azo}-3-hydroxy-1-napthalenecarboxylic acid
  参考文献：
  名称：

  Thrombopoietin mimetics

  摘要：

  非肽TPO类似物已经被揭示，以及一种治疗血小板减少症的方法，在需要的哺乳动物中，包括人类，在这种哺乳动物中给予选择的羟基-1-偶氮萘衍生物的有效量。

  公开号：

  US06670387B1
• 作为产物：
  描述：

  3,4-二甲基苯肼 在 对甲苯磺酰叠氮 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 4-diazo-1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-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

文献信息

• Selective Synthesis of Pyrazolonyl Spirodihydroquinolines or Pyrazolonyl Spiroindolines under Aerobic or Anaerobic Conditions
  作者：Caiyun Yu、Yuanshuang Xu、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.orglett.2c03952

  日期：2022.12.30

  seven-membered ruthenacycle species serving as a key intermediate through Ru(II)-catalyzed C–H/N–H bonds metalation, carbene formation, and its migratory insertion. When the reaction is carried out under air, the key intermediate undergoes reductive elimination to afford spirodihydroquinoline. When the reaction is run under argon, the key intermediate undergoes protonation and intramolecular nucleophilic

  本文介绍的是通过 2-烯基苯胺与重氮吡唑啉酮的正式 [5 + 1] 或 [4 + 1] 螺环化，条件控制选择性合成吡唑啉基螺二氢喹啉或吡唑啉基螺二氢吲哚。从机理上讲，标题产物的形成涉及通过 Ru(II) 催化的 C-H/N-H 键金属化、卡宾形成及其迁移，初始生成吡唑啉基螺稠合七元钌环物种作为关键中间体插入。当反应在空气中进行时，关键中间体发生还原消除，得到螺二氢喹啉。当反应在氩气下运行时，关键中间体会发生质子化和分子内亲核加成反应，生成螺二氢吲哚。2 )–H 键，允许在广泛的底物上快速和选择性地组装有价值的螺旋支架。