(E)-5-imino-4-(2-phenylhydrazineylidene)-4,5-dihydro-1H-pyrazol-3-amine

• 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: (E)-5-imino-4-(2-phenylhydrazineylidene)-4,5-dihydro-1H-pyrazol-3-amine
• 化学式: C₉H₁₀N₆
• mdl: MFCD00486945
• 分子量: 202.219
• InChiKey: OKZNBFAXFGTZRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101.15
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (苯基亚肼基)丙二腈 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 以76%的产率得到(E)-5-imino-4-(2-phenylhydrazineylidene)-4,5-dihydro-1H-pyrazol-3-amine
  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：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
• Multi-component reactions for the synthesis of pyrazolo [1,5-a]quinoline derivatives together with their cytotoxic evaluations
  作者：Rafat M. Mohareb、Maher H.E. Helal、Amany E. Mayhoub、Amira E.M. Abdallah

  DOI：10.4314/bcse.v37i3.14

  日期：——

  ABSTRACT. A new approaches for the synthesis of novel pyrazolo[1,5-a]quinazoline 8a-f and pyrazolo[1,5-a]quinazolin-6-one 10a-s and 12a-s derivatives were obtained using 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 5a-f via their multi-component reactions. The later pyrazole derivatives were prepared via arylhydrazone derivatives 3a-f. The structures of the synthesized compounds were established based on their respective analytical data. On the other hand, the cytotoxic effects of the synthesized compounds were obtained against the 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. The obtained results showed that compounds 8c, 8f, 10c, 10i, 10l, 10p, 10s, 12c, 12i, 12l, 12p and, 12s were the most cytotoxic compounds. In most cases the presence of the electronegative Cl group enhanced the cytotoxicity of the tested compound.   KEY WORDS: Multi-component reactions, Pyrazolo[1,5-a]quinazoline, Pyrazolo[1,5-a]quinazolin-6-one, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(3), 717-734.                                                                DOI: https://dx.doi.org/10.4314/bcse.v37i3.14

  摘要。使用 4-(2-苯肼基)-4H-吡唑-3-胺衍生物 5a-f 通过多组分反应合成了新型吡唑并[1,5-a]喹唑啉 8a-f 和吡唑并[1,5-a]喹唑啉-6-酮 10a-s 和 12a-s 衍生物。之后的吡唑衍生物是通过芳基腙衍生物 3a-f 制备的。根据各自的分析数据确定了合成化合物的结构。另一方面，以 foretinib 为阳性对照，采用标准 MTT 法，在体外测定了合成化合物对 A549、HT-29、MKN-45、U87MG、SMMC-7721 和 H460 六种癌细胞株的细胞毒性作用。结果表明，化合物 8c、8f、10c、10i、10l、10p、10s、12c、12i、12l、12p 和 12s 是细胞毒性最强的化合物。在大多数情况下，电负性 Cl 基团的存在增强了受试化合物的细胞毒性； ； 关键词：多组分反应 吡唑并[1,5-a]喹唑啉 吡唑并[1,5-a]喹唑啉-6-酮 细胞毒性 ； Bull.Chem.Soc. Ethiop.2023, 37(3), 717-734. ； DOI: https://dx.doi.org/10.4314/bcse.v37i3.14