2,4-diamino-7-phenylpyrazolo[1,5-a][1,3,5]triazine | 115231-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-diamino-7-phenylpyrazolo[1,5-a][1,3,5]triazine
• 英文别名: 7-Phenylpyrazolo[1,5-a][1,3,5]triazine-2,4-diamine
• CAS: 115231-49-7
• 化学式: C₁₁H₁₀N₆
• 分子量: 226.241
• InChiKey: PYSGDQZZNYXTRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-diamino-7-phenylpyrazolo[1,5-a][1,3,5]triazine 在 氢氧化钾 作用下， 生成 2-amino-7-phenyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
  参考文献：
  名称：

  Checchi; Ridi, Gazzetta Chimica Italiana, 1957, vol. 87, p. 597,611

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基-5-苯基吡唑 在 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.5h， 生成 2,4-diamino-7-phenylpyrazolo[1,5-a][1,3,5]triazine
  参考文献：
  名称：

  4-Amino-substituted pyrazolo[1,5-a][1,3,5]triazin-2-amines: a new practical synthesis and biological activity

  摘要：

  The trichloromethyl moiety was successfully employed as a leaving group in nucleophilic substitutions with various amines for the synthesis of 4-amino-substituted pyrazolo[1,5-a][1,3,5]triazin-2-amines. The key precursor for this reaction, 4-trichloromethylpyrazolo[1,5-a][1,3,5]triazin-2-amine, was prepared via the solvent-dependent condensation of 5-guanidino-3-phenylpyrazole with trichloroacetonitrile. In a broad biological activity screening, some of the prepared compounds were identified as CGRP receptor antagonists. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.057

文献信息

• Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines
  作者：Anton V. Dolzhenko、Felicia Phei Lin Lim、Koon Kee Kow、Eng Hwa Yeo、Sek Chuen Chow

  DOI：10.3987/com-16-13464

  日期：——

  Novel fluorinated 4-benzylamino-7-phenylpyrazolo [1,5-c][1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reaction afforded 7-phenyl-4-trichloromethylpyrazolo[1,5-a][1,3,5]-triazin-2-amine as the main product. This key intermediate underwent nucleophilic replacement of the trichloromethyl group with fluorinated benzylamines providing a series of the target compounds. Antiproliferative activity of the prepared compounds against Jurkat T cells was explored using MTS assay. Morphological changes observed in cells treated by the most potent compounds of this series, suggested that these compounds induced apoptosis in cells.