4-[(4-Methoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine | 99285-51-5

• 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: 4-[(4-Methoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine
• 英文别名: KP-15792；3,5-Diamino-4-(p-methoxyphenyl)hydrazonopyrazole；NSC21678
• CAS: 99285-51-5
• 化学式: C₁₀H₁₂N₆O
• mdl: MFCD00852739
• 分子量: 232.245
• InChiKey: CYYROHZWNLFOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  107.88
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[(4-Methoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine 生成 2-(4-Methoxy-phenyl)-2H-[1,2,3]triazole-4-carbonitrile
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  [2-(4-甲氧苯基)肼亚基]丙二腈 生成 4-[(4-Methoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine
  参考文献：
  名称：

  摘要：

  DOI：

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。
• SAR study of 4-arylazo-3,5-diamino-1<i>H</i>-pyrazoles: identification of small molecules that induce dispersal of <i>Pseudomonas aeruginosa</i> biofilms
  作者：Charlotte U. Jansen、Jesper Uhd、Jens B. Andersen、Louise D. Hultqvist、Tim H. Jakobsen、Martin Nilsson、Thomas E. Nielsen、Michael Givskov、Tim Tolker-Nielsen、Katrine M. Qvortrup

  DOI：10.1039/d1md00275a

  日期：——

  4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacophore can be further optimized, for example, via substitutions in the aryl ring. The SAR study revealed the very potent anti-biofilm compound 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1H-pyrazol-3-amine (2).

  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 )。
• 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：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。
• Multi-component synthesis of pyrazolo[1,5-a]quinazoline, thiazole and thiophene derivatives as cytotoxic agents
  作者：Rafat M. Mohareb、Maher H. E. Helal、Amany E. Mayhoub、Amira E. M. Abdallah

  DOI：10.4314/bcse.v37i6.17

  日期：——

  ABSTRACT. This study demonstrated the synthesis of a number of pyrazolo[1,5-a]quinazoline derivatives about 24 products based on the starting material 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 1a-f. Moreover, other ring systems including thiophene, pyrazole, thiazole and pyran (16 compounds) were prepared based on another starting compounds 2-(furan-2-ylmethylene)cyclohexane-1,3-dione 10  and 5,5-dimethyl-3-phenyl-2-thioxo-2,3,5,6-tetrahydrobenzo[d]thiazol-7(4H)-one 18. The multi-component reaction was used to prepare all the previous compounds. The structures of all the synthesised compounds were confirmed by the analytical and spectral data. Some selected compounds were chosen to test their anticancer activity against six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, SMMC-7721 and, H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. Toward the tested cell lines, nine compounds were the most cytotoxic compounds. The results obtained revealed that the synthesized compounds are good cytotoxic agents and of great impact for future work. KEY WORDS: Multi-component reactions, Pyrazolo[1,5-a]quinazoline, Thiophene, Thiazole, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(6), 1521-1538. DOI: https://dx.doi.org/10.4314/bcse.v37i6.17

  摘要本研究以起始化合物 4-(2-苯肼基)-4H-吡唑-3-胺衍生物 1a-f 为基础，合成了一系列吡唑并[1,5-a]喹唑啉衍生物，约 24 个产物。此外，以另一种起始化合物 2-(呋喃-2-亚甲基)环己烷-1,3-二酮 10 和 5,5-二甲基-3-苯基-2-硫酮-2,3,5,6-四氢苯并[d]噻唑-7(4H)-酮 18 为基础，制备了包括噻吩、吡唑、噻唑和吡喃在内的其他环系统（16 个化合物）。多组分反应用于制备之前的所有化合物。分析和光谱数据证实了所有合成化合物的结构。利用 foretinib 作为阳性对照和体外标准 MTT 试验，选择了一些化合物来测试它们对六种癌细胞株（即 A549、HT-29、MKN-45、U87MG、SMMC-7721 和 H460）的抗癌活性。在测试的细胞系中，有九种化合物的细胞毒性最强。研究结果表明，合成的化合物具有良好的细胞毒性，对今后的工作具有重要影响； 关键词：多组分反应 吡唑并[1,5-a]喹唑啉 噻吩 噻唑 细胞毒性 ； Bull.Chem.Soc. Ethiop.2023, 37(6), 1521-1538.DOI: https://dx.doi.org/10.4314/bcse.v37i6.17