3-hydroxyphenylhydrazonopropanedinitrile | 96382-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxyphenylhydrazonopropanedinitrile
• 英文别名: 2-[(3-hydroxyphenyl)-hydrazono]malononitrile；2-(3-Hydroxyphenyl)hydrazonopropanedinitrile；2-[(3-hydroxyphenyl)hydrazinylidene]propanedinitrile
• CAS: 96382-70-6
• 化学式: C₉H₆N₄O
• 分子量: 186.173
• InChiKey: XPHHWVZARKXKST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxyphenylhydrazonopropanedinitrile 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 以34%的产率得到(E)-3-(2-(3-amino-5-imino-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazineyl)phenol
  参考文献：
  名称：

  4-arylazo-3,5-diamino-1H-pyrazoles 的 SAR 研究：鉴定诱导铜绿假单胞菌生物膜分散的小分子

  摘要：

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。

  DOI：

  10.1039/d1md00275a
• 作为产物：
  描述：

  3-氨基苯酚 、 丙二腈 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 生成 3-hydroxyphenylhydrazonopropanedinitrile
  参考文献：
  名称：

  4-arylazo-3,5-diamino-1H-pyrazoles 的 SAR 研究：鉴定诱导铜绿假单胞菌生物膜分散的小分子

  摘要：

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。

  DOI：

  10.1039/d1md00275a

文献信息

• Pyrazole compounds
  申请人：——

  公开号：US20030060453A1

  公开（公告）日：2003-03-27

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  提供药物组合物和化合物。发明的化合物显示出抗增殖活性，并且可能促进缺乏正常细胞周期和死亡调控的细胞的凋亡。发明的一个实施例提供了化合物与生理可接受载体组合的药物组合物。该药物组合物可用于治疗过度增殖障碍，包括肿瘤生长、淋巴增殖性疾病、血管生成。发明的化合物是取代吡唑和吡唑啉。
• Immugenic compositions and diagnostic and therapeutic uses thereof
  申请人：Zhang Zaihui

  公开号：US20050272709A1

  公开（公告）日：2005-12-08

  Pharmaceutical compositions and compounds are provided. The compounds of the invention deomonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  本发明提供了制药组合物和化合物。本发明的化合物表现出抗增殖活性，并可能促进缺乏正常细胞周期和死亡调节的细胞凋亡。在本发明的一种实施例中，提供了化合物与生理可接受载体的制药组合物。这些制药组合物可用于治疗高增殖性疾病，包括肿瘤生长、淋巴增殖性疾病、血管生成等疾病。本发明的化合物是取代的吡唑和吡唑啉。
• Hydrazonopyrazole derivatives and their use as therapeutics
  申请人：Valocor Therapeutics, Inc.

  公开号：US07875728B2

  公开（公告）日：2011-01-25

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  本发明提供了药物组合物和化合物。本发明的化合物表现出抗增殖活性，并可能促进缺乏正常细胞周期和死亡调节的细胞凋亡。在本发明的一种实施例中，提供了化合物与生理上可接受的载体组合的药物组合物。这些药物组合物在治疗增生性疾病方面是有用的，这些疾病包括肿瘤生长，淋巴增生性疾病和血管生成。本发明的化合物是取代的吡唑和吡唑烷。
• HYDRAZONOPYRAZOLE DERIVATIVES AND THEIR USE AS THERAPEUTICS
  申请人：Zhang Zaihui

  公开号：US20110237783A1

  公开（公告）日：2011-09-29

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  本发明提供了药物组合物和化合物。本发明的化合物表现出抗增殖活性，并可能促进缺乏正常细胞周期和死亡调节的细胞凋亡。在本发明的一个实施例中，提供了与生理学上可接受的载体结合的化合物的药物组合物。这些药物组合物在治疗增生性疾病方面有用，这些疾病包括肿瘤生长、淋巴增生性疾病和血管生成等疾病。本发明的化合物是取代的吡唑和吡唑啉。
• 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.