3-Methyl-1,6-diphenylpyrazolo[3,4-b]pyrazine-5-carbonyl chloride | 214914-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-1,6-diphenylpyrazolo[3,4-b]pyrazine-5-carbonyl chloride
• CAS: 214914-37-1
• 化学式: C₁₉H₁₃ClN₄O
• 分子量: 348.791
• InChiKey: FXXPLGAVNZASMU-UHFFFAOYSA-N

物化性质

• 沸点：
  492.604±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.368±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Methyl-1,6-diphenylpyrazolo[3,4-b]pyrazine-5-carbonyl chloride 在 吡啶 、 二硫化碳 、 aluminum (III) chloride 作用下， 反应 9.0h， 生成 [(Z)-(12-methyl-14-phenyl-10,13,14,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2,4,6,9,11(15),12-heptaen-8-ylidene)amino]thiourea
  参考文献：
  名称：

  First synthesis and biological evaluation of indeno[2,1- e ]pyrazolo[3,4- b ]pyrazin-5-one and related derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.01.025
• 作为产物：
  描述：

  1,6-diphenyl-3-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid 在 氯化亚砜 作用下， 反应 2.0h， 以78%的产率得到3-Methyl-1,6-diphenylpyrazolo[3,4-b]pyrazine-5-carbonyl chloride
  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

• 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.
• 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)。
• 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.