3-(4-氯苯基)-1H-吡唑-5-甲酰肼 | 890012-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-氯苯基)-1H-吡唑-5-甲酰肼
• 英文名称: 3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide
• 英文别名: 3-(4-cholorophenyl)-1H-pyrazole-5-carbohydrazide
• CAS: 890012-50-7
• 化学式: C₁₀H₉ClN₄O
• mdl: MFCD01038389
• 分子量: 236.661
• InChiKey: CSHLSZFCPXYIAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)-1H-吡唑-5-甲酰肼 在 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (+/-)-trans-N-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives

  摘要：

  As a part of our research to develop novel antitubercular and antimicrobial agents, a series of 3-(4-chlorophenyl)-4-substituted pyrazoles have been synthesised. These compounds were tested for antitubercular activity in vitro against Mycobacterium tuberculosis H37Rv strain using the BACTEC 460 radiometric system, antifungal activity against a pathogenic strain of fungi and antibacterial activity against grampositive and gram-negative organisms. Among them tested, many compounds showed good to excellent antimicrobial and antitubercular activity. The results suggest that hydrazones, 2-azetidinones and 4-thiazolidinones bearing a core pyrazole scaffold would be potent antimicrobial and antitubercular agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.063
• 作为产物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 在 盐酸肼 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3-(4-氯苯基)-1H-吡唑-5-甲酰肼
  参考文献：
  名称：

  吡唑-恶二唑共轭物：合成，抗增殖活性和抑制微管蛋白聚合†

  摘要：

  合成了许多吡唑-恶二唑偶联物，并评估了它们在各种人类癌细胞系中作为抗增殖剂的能力。这些缀合物由彼此紧密连接的吡唑和恶二唑支架组成，没有任何间隔子作为两个结构类别。I类具有三甲氧基取代基，II类具有在其A环上的3,4-（亚甲基二氧基）取代基。在这些结合物中，11a，11d和11f表现出强的细胞毒性，IC 50值为1.5μM至11.2μM，并抑制微管蛋白的IC 50聚合分别为1.3μM，3.9μM和2.4μM。细胞周期分析表明，用这些缀合物处理会导致细胞在G2 / M期积累，并破坏微管网络。斑马鱼胚胎的阐明表明，缀合物导致发育缺陷。分子对接模拟确定了这些有效结合物在微管蛋白秋水仙碱位点的结合模式。

  DOI：

  10.1039/c4ob01152j

文献信息

• Synthesis and biological evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives
  作者：P. Horrocks、M. R. Pickard、H. H. Parekh、S. P. Patel、Ravindra B. Pathak

  DOI：10.1039/c3ob27290g

  日期：——

  3-(4-Chlorophenyl)-4-substituted pyrazole derivatives were synthesised and tested for their in vitro antifungal activity. Some compounds showed very good antifungal activity against four pathogenic strains of fungi. The same compounds exhibited an interesting activity against the tested strain of Mycobacterium tuberculosis H37Rv. The results suggest that 1,3,4-oxadiazoles and 5-pyrazolinones bearing

  合成了3-（4-氯苯基）-4-取代的吡唑衍生物，并测试了它们的体外抗真菌活性。一些化合物对四种病原性真菌显示出非常好的抗真菌活性。相同的化合物对测试的结核分枝杆菌H37Rv菌株表现出令人感兴趣的活性。结果表明，带有核心吡唑支架的1,3,4-恶二唑和5-吡唑啉酮可能是有前途的抗真菌和抗结核药。
• Synthesis, X-ray crystal structure and optical properties of novel 5-(3-aryl-1H-pyrazol-5-yl)-2-(6-methoxy-3-methylbenzofuran-2-yl)-1,3,4-oxadiazole
  作者：Zhen-Ju Jiang、Jin-Ting Liu、Hong-Shui Lv、Bao-Xiang Zhao

  DOI：10.1016/j.saa.2011.10.021

  日期：2012.2

  position of benzene moiety. The maximum emission spectra of compounds in two different solvents were mainly dependent on groups in N-1 position of pyrazole moiety. The intensity of absorption and fluorescence was also correlated with substituents on the aryl ring bonded to pyrazole moiety. In addition, the absorption and emission spectra of these compounds change with increasing solvent polarity.

  由6-苯甲酸酯合成了一系列新颖的5-（3-芳基-1H-吡唑-5-基）-2-（6-甲氧基-3-甲基苯并呋喃-2-基）-1,3,4-恶二唑衍生物。甲氧基-3-甲基苯并呋喃-2-羧酸和3-芳基-1H-吡唑-5-羧酸乙酯。通过IR，（1）H NMR和HRMS光谱确定获得的化合物的结构。通常，化合物7e的空间结构通过使用X射线衍射分析来确定。研究了该化合物在二氯甲烷和乙腈中的紫外可见吸收和荧光光谱特征。结果表明，取决于吡唑部分的N-1位和苯部分的对位的取代基，化合物的最大吸收在321nm至339nm之间变化。化合物在两种不同溶剂中的最大发射光谱主要取决于吡唑部分N-1位的基团。吸收和荧光的强度还与结合到吡唑部分的芳基环上的取代基相关。另外，这些化合物的吸收和发射光谱随溶剂极性的增加而变化。
• Synthesis, Structure-Activity Relationship, and Pharmacophore Modeling Studies of Pyrazole-3-Carbohydrazone Derivatives as Dipeptidyl Peptidase IV Inhibitors
  作者：Deyan Wu、Fangfang Jin、Weiqiang Lu、Jin Zhu、Cui Li、Wei Wang、Yun Tang、Hualiang Jiang、Jin Huang、Guixia Liu、Jian Li

  DOI：10.1111/j.1747-0285.2012.01365.x

  日期：2012.6

  Type 2 diabetes mellitus (T2DM) is a metabolic disease and a major challenge to healthcare systems around the world. Dipeptidyl peptidase IV (DPP‐4), a serine protease, has been rapidly emerging as an effective therapeutic target for the treatment for T2DM. In this study, a series of novel DPP‐4 inhibitors, featuring the pyrazole‐3‐carbohydrazone scaffold, have been discovered using an integrated approach of structure‐based virtual screening, chemical synthesis, and bioassay. Virtual screening of SPECS Database, followed by enzymatic activity assay, resulted in five micromolar or low‐to‐mid‐micromolar inhibitory level compounds (1–5) with different scaffold. Compound 1 was selected for the further structure modifications in considering inhibitory activity, structural variability, and synthetic accessibility. Seventeen new compounds were synthesized and tested with biological assays. Nine compounds (6e, 6g, 6k–l, and 7a–e) were found to show inhibitory effects against DPP‐4. Molecular docking models give rational explanation about structure–activity relationships. Based on eight DPP‐4 inhibitors (1–5, 6e, 6k, and 7d), the best pharmacophore model hypo1 was obtained, consisting of one hydrogen bond donor (HBD), one hydrogen bond acceptor (HBA), and two hydrophobic (HY) features. Both docking models and pharmacophore mapping results are in agreement with pharmacological results. The present studies give some guiding information for further structural optimization and are helpful for future DPP‐4 inhibitors design.
• Pyrazole–oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization
  作者：Ahmed Kamal、Anver Basha Shaik、Sowjanya Polepalli、Vangala Santosh Reddy、G. Bharath Kumar、Soma Gupta、K. V. S. Rama Krishna、Ananthamurthy Nagabhushana、Rakesh K. Mishra、Nishant Jain

  DOI：10.1039/c4ob01152j

  日期：——

  4-(methylenedioxy) substituent on their A rings. Among these conjugates, 11a, 11d and 11f manifest potent cytotoxicity with IC50 values ranging from 1.5 μM to 11.2 μM and inhibit tubulin polymerization with IC50 values of 1.3 μM, 3.9 μM and 2.4 μM respectively. The cell cycle assay showed that treatment with these conjugates results in accumulation of cells in the G2/M phase and disrupts the microtubule network

  合成了许多吡唑-恶二唑偶联物，并评估了它们在各种人类癌细胞系中作为抗增殖剂的能力。这些缀合物由彼此紧密连接的吡唑和恶二唑支架组成，没有任何间隔子作为两个结构类别。I类具有三甲氧基取代基，II类具有在其A环上的3,4-（亚甲基二氧基）取代基。在这些结合物中，11a，11d和11f表现出强的细胞毒性，IC 50值为1.5μM至11.2μM，并抑制微管蛋白的IC 50聚合分别为1.3μM，3.9μM和2.4μM。细胞周期分析表明，用这些缀合物处理会导致细胞在G2 / M期积累，并破坏微管网络。斑马鱼胚胎的阐明表明，缀合物导致发育缺陷。分子对接模拟确定了这些有效结合物在微管蛋白秋水仙碱位点的结合模式。
• Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives
  作者：Ravindra B. Pathak、P.T. Chovatia、H.H. Parekh

  DOI：10.1016/j.bmcl.2012.05.063

  日期：2012.8

  As a part of our research to develop novel antitubercular and antimicrobial agents, a series of 3-(4-chlorophenyl)-4-substituted pyrazoles have been synthesised. These compounds were tested for antitubercular activity in vitro against Mycobacterium tuberculosis H37Rv strain using the BACTEC 460 radiometric system, antifungal activity against a pathogenic strain of fungi and antibacterial activity against grampositive and gram-negative organisms. Among them tested, many compounds showed good to excellent antimicrobial and antitubercular activity. The results suggest that hydrazones, 2-azetidinones and 4-thiazolidinones bearing a core pyrazole scaffold would be potent antimicrobial and antitubercular agents. (C) 2012 Elsevier Ltd. All rights reserved.