5-amino-3-methyl-4-nitroso-1-phenylpyrazole | 52943-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-3-methyl-4-nitroso-1-phenylpyrazole
• 英文别名: 3-methyl-4-nitroso-1-phenyl-1H-pyrazol-5-amine；5-methyl-4-nitroso-2-phenylpyrazol-3-amine
• CAS: 52943-85-8
• 化学式: C₁₀H₁₀N₄O
• mdl: MFCD00100952
• 分子量: 202.216
• InChiKey: PKNDMLXSFRJDDY-UHFFFAOYSA-N

物化性质

• 沸点：
  405.8±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  >30.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-amino-3-methyl-4-nitroso-1-phenylpyrazole 在 吡啶 、 sodium hydroxide 、 硫酸 、 水 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyrazine-5-carbohydrazide
  参考文献：
  名称：

  Facile synthesis of some new pyrazolo [3,4-b] pyrazines and their antifungal activity

  摘要：

  The synthesis of new pyrazolo[3,4-b]pyrazines and related heterocycles has been reported. The key intermediate 1,6-diphenyl-3-methyl-1 H-pyrazolo[ 3,4-b]pyrazine-5-carbonitrile 2 was obtained in one pot synthesis from the reaction of 5-amino-3-methyl-4-nitroso-1-phenyl-pyrazole 1 with benzoylacetonitrile. Modest antifungal activity was shown for some of the prepared compounds. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00014-7
• 作为产物：
  描述：

  3-phenylhydrazono-butyronitrile 在 乙醇 、 nitrogen oxides 作用下， 生成 5-amino-3-methyl-4-nitroso-1-phenylpyrazole
  参考文献：
  名称：

  Walther, Journal fur praktische Chemie (Leipzig 1954), 1897, vol. <2> 55, p. 143

  摘要：

  DOI：

文献信息

• Anticancer and Anti-Inflammatory Activities of Some New Pyrazolo[3,4-b]pyrazines
  作者：Hussein El-Kashef、Talaat El-Emary、Pierre Verhaeghe、Patrice Vanelle、Maha Samy

  DOI：10.3390/molecules23102657

  日期：——

  New derivatives of pyrazolo[3,4-b]pyrazines and related heterocycles were synthesized using 5-amino-3-methyl-4-nitroso-1-phenyl-pyrazole (1) as a starting material. The 5-acetyl derivative 15 was shown to be a useful key intermediate for the synthesis of several derivatives of pyrazolopyrazines. Some of the prepared compounds were evaluated for their anti-inflammatory and anti-breast cancer MCF-7 cell

  使用 5-氨基-3-甲基-4-亚硝基-1-苯基-吡唑 (1) 作为起始材料合成了吡唑并 [3,4-b] 吡嗪和相关杂环的新衍生物。5-乙酰基衍生物 15 被证明是合成几种吡唑并吡嗪衍生物的有用关键中间体。评估了一些制备的化合物的抗炎和抗乳腺癌 MCF-7 细胞系活性。SAR研究表明化合物15和29表现出显着的抗炎活性，其中15表现出与参考药物吲哚美辛相同的活性。另一方面，化合物25i、25j对MCF-7乳腺癌细胞系显示出非常显着的抑制活性(p<0.001)。
• Composition for dyeing keratin fibers which contain at least one
  申请人：L'Oreal

  公开号：US06099592A1

  公开（公告）日：2000-08-08

  The invention relates to novel compositions for the oxidation dyeing of keratin fibers, comprising at least one specific diaminopyrazole derivative, to the dyeing process using this composition, to novel diaminopyrazole derivatives and to a process for their preparation.

  本发明涉及用于角蛋白纤维氧化染色的新型组合物，其包含至少一种特定的二氨基吡唑衍生物，涉及使用该组合物的染色过程，涉及新型二氨基吡唑衍生物，以及涉及它们的制备过程。
• Reactivity of pyrazolo[4,3-<i>c</i>][1,2,5]oxadiazin-3(5<i>H</i>)-ones toward<i>C</i>-nucleophiles: Synthesis of pyrazolo[3,4-<i>b</i>]pyrazines
  作者：P. Giori、A. C. Veronese、T. Poli、C. B. Vicentini、M. Manfrini、M. Guarneri

  DOI：10.1002/jhet.5570230255

  日期：1986.3

  The reaction of pyrazolo[4,3-c][1,2,5]oxadiazin-3(5H)-ones 1 with carbanions prepared in situ from compounds containing an activated methylene group afforded pyrazolo[3,4-b]pyrazines 4–13 in good yields. The possible reaction mechanism is proposed and discussed.

  吡唑并[4,3- c ] [1,2,5]恶二嗪-3（5 H）-ones 1与由含活化亚甲基的化合物原位制备的碳负离子反应，得到吡唑并[3,4- b ]吡嗪4–13，丰产。提出并讨论了可能的反应机理。
• Composition for dyeing keratin fibers which contain at least one diaminopyrazole, dyeing process, novel diaminopyrazoles and process for their preparation
  申请人：L'Oreal

  公开号：US06338741B1

  公开（公告）日：2002-01-15

  The invention relates to novel compositions for the oxidation dyeing of keratin fibers, comprising at least one specific diaminopyrazole derivative, to the dyeing process using this composition, to novel diaminopyrazole derivatives and to a process for their preparation.

  该发明涉及一种用于氧化染色角蛋白纤维的新型组合物，包括至少一种特定的二氨基吡唑衍生物，以及使用该组合物的染色过程，新型二氨基吡唑衍生物和其制备过程。
• Microwave-assisted synthesis of fused pyrazolo[3,4-b]pyrazines by the reaction of ortho-aminonitrosopyrazoles and cyclic β-diketones
  作者：Jairo Quiroga、Norha E. Sánchez、Paola Acosta、Braulio Insuasty、Rodrigo Abonia

  DOI：10.1016/j.tetlet.2012.04.083

  日期：2012.6

  Novel fused pyrazolo[3,4-b]pyrazines 3 were prepared by assisted microwave cyclocondensation reaction of ortho-aminonitrosopyrazoles 1 and cyclic β-diketones 2 in dimethylformamide. This protocol provides a simple procedure for the synthesis of the title compounds with the advantages of easy work-up, mild reaction conditions and good yields.

  新型的稠合吡唑并[3,4- b ]吡嗪3是通过在二甲基甲酰胺中进行的邻氨基亚硝基吡唑1和环状β-二酮2的微波环缩合反应制备的。该方案为标题化合物的合成提供了一种简单的方法，具有易于后处理，温和的反应条件和良好的收率的优点。