3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazole-4-carbaldehyde | 1187969-22-7

• 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-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-(4-chlorophenyl)-1-(4-nitrophenyl)pyrazole-4-carbaldehyde
• CAS: 1187969-22-7
• 化学式: C₁₆H₁₀ClN₃O₃
• 分子量: 327.727
• InChiKey: OZIKOVBOURAYGY-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  538.9±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-氨丙基)-4-甲基哌嗪 、 3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazole-4-carbaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 N-[[3-(4-chlorophenyl)-1-(4-nitrophenyl)pyrazol-4-yl]methyl]-3-(4-methylpiperazin-1-yl)propan-1-amine
  参考文献：
  名称：

  鉴定出一系列1,3,4-三取代的吡唑类药物作为新型丙型肝炎病毒进入抑制剂

  摘要：

  在本报告中，我们描述了新型吡唑类似物作为强效丙型肝炎病毒（HCV）进入抑制剂的鉴定。通过使用感染性HCV的表型高通量筛选来鉴定吡唑。合成了一系列吡唑衍生物，并评估了其在感染性细胞培养系统中对HCV的抑制活性。通过评估选定的化合物，我们观察到吡唑不会干扰HCV RNA复制，但会干扰病毒进入，如分别使用HCV复制子和HCV假颗粒进行的实验所示。

  DOI：

  10.1016/j.bmcl.2013.09.039
• 作为产物：
  描述：

  对氯苯乙酮 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Novel Benzimidazoles, Benzothiazoles and Benzofurans Incorporating Pyrazole Moiety as Antiangiogenic Agents

  摘要：

  合成了一些新型苯并咪唑、苯并噻唑和苯并呋喃化合物，并将其与吡唑基团结合，筛选其抗血管生成活性，通过测试它们抑制人脐静脉内皮细胞（HUVEC）增殖、管道形成和对趋化因子的迁移能力。三个化合物19、23和26在非细胞毒浓度下显示出抗血管生成活性。化合物19的活性最强，其趋化活性数据几乎可与阳性对照TNP-470相媲美。化合物42对测试的癌细胞系表现出显著的细胞毒性作用，但与化合物19、23和26相比，其抗血管生成活性较低。所有测试化合物与TNP-470相反，干扰了HUVEC对血管内皮生长因子的迁移功能，而不是内皮细胞的增殖或管道形成。此外，使用分子操作环境模块获得了化合物19和26与激酶插入域受体结合的对接构象。

  DOI：

  10.1055/s-0031-1295483

文献信息

• Novel pyrazine based anti-tubercular agents: Design, synthesis, biological evaluation and in silico studies
  作者：Nayera W. Hassan、Manal N. Saudi、Yasser S. Abdel-Ghany、Azza Ismail、Perihan A. Elzahhar、Dharmarajan Sriram、Rasha Nassra、Marwa M. Abdel-Aziz、Soad A. El-Hawash

  DOI：10.1016/j.bioorg.2020.103610

  日期：2020.3

  TB continues to be a leading health threat despite the availability of powerful anti-TB drugs. We report herein the design and synthesis of various hybrid molecules comprising pyrazine scaffold and various formerly identified anti-mycobacterial moieties. Thirty-one compounds were screened in vitro for their activity against Mycobacterium tuberculosis H37Rv strain using MABA assay. The results revealed

  尽管有强大的抗结核药物，结核病仍然是主要的健康威胁。我们在本文中报道了包括吡嗪支架和各种先前鉴定的抗分枝杆菌部分的各种杂合分子的设计和合成。使用MABA分析在体外筛选了31种化合物对结核分枝杆菌H37Rv菌株的活性。结果表明，六种化合物（8a，8b，8c，8d，14b和18）显示出对Mtb的显着活性，MIC值≤6.25µg / ml，而吡嗪酰胺为6.25 µg / ml。然后使用MTT分析法评估活性最高的化合物对PBMC正常细胞系的体外细胞毒性，并显示SI>200。已针对新化合物的目标捕捞进行了多项计算机研究，例如基于形状的相似性，药效团映射和反向对接。基于此多步骤目标捕捞研究，我们建议泛酸合成酶可能是负责这些化合物作用的目标。然后将活性最高的化合物成功地对接至具有良好结合相互作用的泛酸合成酶的活性位点。此外，还对物理化学的计算机模拟预测，ADMET和类药物特性进行了测定，表明化合物8b，
• Synthesis and Biological Evaluation of the Pyrazole Class of Cyclooxygenase- 2-Inhibitors
  作者：Samia Rida、Manal Saudi、Amal Youssef、Madiha Halim

  DOI：10.2174/157017809788489909

  日期：2009.6.1

  Several 1,3,4-trisubstituted pyrazole derivatives were synthesized via condensation with the appropriate amine, sulphonamide, acid hydrazide, or benzyl thiosemicarbazide derivatives. The newly synthesized compounds were screened for a possible anti-inflammatory effect in a rat model of air-pouch carrageenan-induced inflammation. The results revealed that some of the newly synthesized compounds exhibited a significant anti-inflammatory effect in terms of reducing exudation and/or leukocytic accumulation at the site of inflammation. Thus, compared to carrageenan-induced inflammation group, compounds 3, 9, 13, and 17 were particularly associated with significant decrease in both the volume of exudate and leukocyte accumulation while compounds 4, 7, 10, 11 and 15 were associated with significant decrease in the volume of inflammatory exudate without a corresponding decrease in the number of accumulated leukocytes. Moreover, a docked pose of compound 17 was obtained and bound to cyclooxygenase active site of COX-2 using Molecular Operating Environment (MOE) module.

  合成了几种1,3,4-三取代吡唑衍生物，这些衍生物通过与适当的胺、磺胺类、酸肼或苄基硫代氨基脲衍生物的缩合反应制得。新合成的化合物在大鼠空气袋卡拉胶诱导的炎症模型中进行了抗炎效果的筛选。结果显示，部分新合成的化合物在减轻渗出和/或白细胞聚集方面表现出显著的抗炎效果。因此，与卡拉胶诱导的炎症组相比，化合物3、9、13和17在渗出液体积和白细胞聚集方面均显著减少，而化合物4、7、10、11和15则在炎症渗出液体积上显著降低，但与白细胞数量的减少无明显关联。此外，化合物17的对接位姿已获得，并结合到COX-2的环氧合酶活性位点，使用了分子操作环境（MOE）模块。
• Design, Synthesis, Molecular Docking Studies and Biological Evaluation of Indole Fused Novel Pyrazole Derivatives
  作者：N. Prasanna Lakshmi、M. Ajitha

  DOI：10.14233/ajchem.2022.23710

  日期：——

  The present work deals with the sequence of indole fused novel pyrazole compounds (5a-l) synthesized by conventional method and were screened for anthelmintic, anticancer activities and molecular docking studies. All the newly synthesized compounds were characterized by IR, 1H NMR and Mass spectral analysis. Further, all the pyrazole derivatives were screened for anthelmintic activity using albendazole as standard drug and anticancer activity against MCF-7 and SKVO3 cell lines by MTT assay method. The results showed that compounds 5b and 5j exhibited good anticancer activity and compounds 5c, 5f, 5h and 5l exhibited potential anthelmintic activity. Additionally, the molecular docking studies of novel pyrazole derivatives were carried out to explain putative bonding interaction between the active site of EGFR enzyme and potent inhibitors.

  本研究涉及一系列吲哚融合新型吡唑化合物（5a-l），采用常规方法合成，并进行了驱虫、抗癌活性和分子对接研究。所有新合成的化合物均通过红外光谱、1H NMR和质谱分析进行了表征。进一步，所有吡唑衍生物均使用阿苯达唑作为标准药物进行了驱虫活性筛选，并通过MTT法对MCF-7和SKVO3细胞系进行了抗癌活性筛选。结果表明，化合物5b和5j表现出良好的抗癌活性，而化合物5c、5f、5h和5l表现出潜在的驱虫活性。此外，对新型吡唑衍生物进行了分子对接研究，以解释EGFR酶的活性位点和潜在抑制剂之间的结合相互作用。
• Synthesis and biological evaluation of novel pyrazolyl-2,4-thiazolidinediones as anti-inflammatory and neuroprotective agents
  作者：Amal M. Youssef、M. Sydney White、Erika B. Villanueva、Ibrahim M. El-Ashmawy、Andis Klegeris

  DOI：10.1016/j.bmc.2010.01.021

  日期：2010.3

  Novel pyrazolyl-2,4-thiazolidinediones were prepared via the reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinediones and substituted benzyl-2,4-thiazolidinediones. The resultant compounds were first evaluated for their anti-inflammatory and neuroprotective properties in vitro. The active compounds were further studied in vivo by using the formalin-induced paw edema and the turpentine oil-induced granuloma pouch bioassays. We identified four novel compounds that showed protective effects in vitro at non-toxic concentrations, and were also effective in the animal models of acute and sub-acute inflammation. (C) 2010 Elsevier Ltd. All rights reserved.