(E)-4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-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: (E)-4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
• 化学式: C₁₄H₁₆N₈O
• 分子量: 312.334
• InChiKey: MVLHTHXONXMDNX-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  132.37
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 、 丙烯腈 在 吡啶 作用下， 以 水 为溶剂， 反应 4.0h， 以78%的产率得到(E)-3-{3,5-diamino-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)diazenyl]-1H-pyrazol-1-yl}propanenitrile
  参考文献：
  名称：

  衍生自4取代的安替比林的一些新吡唑基，异恶唑基，嘧啶基，吡哒嗪基和吡咯并哒嗪基的衍生物，结构和生物学研究

  摘要：

  （1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1 H-吡唑-4-基）羰基肼基二氰化物被用作合成新型吡唑，异恶唑，嘧啶的关键中间体和哒嗪衍生物。通过元素分析和光谱数据（IR，1 H-NMR，13 C-NMR和质谱）对新合成的化合物进行了表征。测试了这些化合物对革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）的体外抗菌活性。）。使用扩散琼脂技术针对两种真菌Fabtrytis fabae和Fusarium oxysporum的菌株测试了所研究的化合物。生物学结果清楚地表明，大多数合成的化合物显示出对所用微生物的中等至中等活性。

  DOI：

  10.1002/jhet.2707
• 作为产物：
  描述：

  4-氨基安替比林 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (E)-4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  4-Arylazo-3,5-diamino-1H-pyrazole CDK Inhibitors:  SAR Study, Crystal Structure in Complex with CDK2, Selectivity, and Cellular Effects

  摘要：

  In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl] phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.

  DOI：

  10.1021/jm0605740

文献信息

• AZO DERIVATIVES CONTAINING A PYRAZOLINONE UNIT FOR DYEING KERATIN FIBRES
  申请人：Fadli Aziz

  公开号：US20100269269A1

  公开（公告）日：2010-10-28

  The subject of the present invention is azo derivatives containing a pyrazolinone unit having the following formula (I), their mesomeric forms, their addition salts with an acid and their solvates and their use for dyeing keratin fibers. The subject of the invention is also a composition for dying keratin fibers comprising at least one azo derivative containing a pyrazolinone unit of formula (I) as direct dye, and the method for dyeing keratin fibers using this composition. The present invention makes it possible in particular to obtain chromatic colours that are resistant to the various attacks to which the hair may be subjected, in particular to shampoos and to light.

  本发明的主题是含有以下式(I)的吡唑啉酮单元的偶氮衍生物，它们的共振式形式，它们与酸的加合盐以及它们的溶剂化物，以及它们用于染色角蛋白纤维的用途。本发明的主题还包括一种用于染色角蛋白纤维的组合物，其中至少包括一种含有式(I)的吡唑啉酮单元的偶氮衍生物作为直接染料，以及使用该组合物染色角蛋白纤维的方法。本发明特别能够获得对头发可能遭受的各种攻击，特别是洗发水和光线，具有耐久性的色彩。
• US8034124B2
  申请人：——

  公开号：US8034124B2

  公开（公告）日：2011-10-11
• 4-Arylazo-3,5-diamino-1<i>H</i>-pyrazole CDK Inhibitors:  SAR Study, Crystal Structure in Complex with CDK2, Selectivity, and Cellular Effects
  作者：Vladimír Kryštof、Petr Cankař、Iveta Fryšová、Jan Slouka、George Kontopidis、Petr Džubák、Marián Hajdúch、Josef Srovnal、Walter F. de Azevedo、Martin Orság、Martina Paprskářová、Jakub Rolčík、Aleš Látr、Peter M. Fischer、Miroslav Strnad

  DOI：10.1021/jm0605740

  日期：2006.11.1

  In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl] phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.
• Derivational, Structural, and Biological Studies of Some New Pyrazolyl, Isoxazolyl, Pyrimidinyl, Pyridazinyl, and Pyridopyridazinyl from 4-Substituted Antipyrine
  作者：Ahmed A. Fadda、Ramy Rabie、Samir Bondock、Hassan A. Etman

  DOI：10.1002/jhet.2707

  日期：2017.3

  5‐Dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)carbono‐hydrazonoyl dicyanide was used as a key intermediate for the synthesis of novel pyrazole, isoxazole, pyrimidine, and pyridazine derivatives. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1H‐NMR, 13C‐NMR, and mass spectra). The compounds were tested for their in vitro antibacterial activity against

  （1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1 H-吡唑-4-基）羰基肼基二氰化物被用作合成新型吡唑，异恶唑，嘧啶的关键中间体和哒嗪衍生物。通过元素分析和光谱数据（IR，1 H-NMR，13 C-NMR和质谱）对新合成的化合物进行了表征。测试了这些化合物对革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）的体外抗菌活性。）。使用扩散琼脂技术针对两种真菌Fabtrytis fabae和Fusarium oxysporum的菌株测试了所研究的化合物。生物学结果清楚地表明，大多数合成的化合物显示出对所用微生物的中等至中等活性。