1,6-diphenyl-3-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid | 129227-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,6-diphenyl-3-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid
• 英文别名: 3-Methyl-1,6-diphenylpyrazolo[3,4-b]pyrazine-5-carboxylic acid
• CAS: 129227-54-9
• 化学式: C₁₉H₁₄N₄O₂
• 分子量: 330.346
• InChiKey: NRSOLZZOEWLJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-diphenyl-3-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 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：

  苯甲酰乙腈 在 吡啶 、 sodium hydroxide 作用下， 反应 9.0h， 生成 1,6-diphenyl-3-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid
  参考文献：
  名称：

  一些新型吡唑并[3,4-b]吡嗪的抗癌和抗炎活性

  摘要：

  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)。

  DOI：

  10.3390/molecules23102657

文献信息

• Synthesis and anticonvulsant activity of some new pyrazolo[3,4-b]pyrazines and related heterocycles
  作者：Abdel-Rahman Farghaly、Sabah Esmail、Ahmed Abdel-Zaher、Ali Abdel-Hafez、Hussein El-Kashef

  DOI：10.1016/j.bmc.2014.02.019

  日期：2014.4

  A series of new pyrazolo[3,4-b]pyrazines containing, 1,2,4-oxadiazolyl, thiadiazolyl, imidazothiadiazolyl, thiazolidinonyl, substituents and other different substituents, was synthesized using 1,6-diphenyl-3-methyl-lH-pyrazolo[3,4-b]pyrazine-5-carbonitrile (2) as a starting material. Some of the newly prepared compounds were evaluated for their anticonvulsant activity. Compounds 9a, 13a–d and 14a at

  使用1,6-二苯基-3-甲基-1 H合成了一系列新的吡唑并[3,4- b ]吡嗪类化合物，其中包含1,2,4-恶二唑基，噻二唑基，咪唑并噻二唑基，噻唑烷二酮基，取代基和其他不同的取代基。-吡唑并[3，4- b ]吡嗪-5-腈（2）作为起始原料。对一些新制备的化合物的抗惊厥活性进行了评估。剂量为10 mg / kg的化合物9a，13a – d和14a显示出非常显着的抗惊厥活性，并增加了PTZ引起的强直性惊厥的潜伏时间。化合物9b显示出明显的作用。
• First synthesis and biological evaluation of indeno[2,1- e ]pyrazolo[3,4- b ]pyrazin-5-one and related derivatives
  作者：Talaat El-Emary、Hussein El-Kashef

  DOI：10.1016/j.ejmech.2013.01.025

  日期：2013.4

  The synthesis of indeno[2,1-e]pyrazolo[3,4-b]pyrazin-5-one was achieved by intramolecular Friedel-Crafts reaction of the acid chloride 3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b] pyrazine-5-carboxylic acid chloride (4) using AlCl3 in boiling CS2. Compound 4 proved to be a versatile compound for the synthesis of several Indenopyrazolopyrazinone derivatives. The antibacterial and antifungal activities of selected derivatives were evaluated. (C) 2013 Elsevier Masson SAS. All rights reserved.
• RANGNEKAR, D. W.;DHAMNASKAR, S. V., DYES AND PIGM., 13,(1990) N, C. 241-250
  作者：RANGNEKAR, D. W.、DHAMNASKAR, S. V.

  DOI：——

  日期：——
• 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)。
• Facile synthesis of some new pyrazolo [3,4-b] pyrazines and their antifungal activity
  作者：T.I. El-Emary、A.M.Kamal El-Dean、H.S. El-Kashef

  DOI：10.1016/s0014-827x(98)00014-7

  日期：1998.6

  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.