1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide | 948293-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide
• 英文别名: 2-benzyl-5-phenylpyrazole-3-carbohydrazide
• CAS: 948293-03-6
• 化学式: C₁₇H₁₆N₄O
• 分子量: 292.34
• InChiKey: UFENZVMIJDYPFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.0h， 生成 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-methylbenzylthio)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, crystal structures, fluorescence and xanthine oxidase inhibitory activity of pyrazole-based 1,3,4-oxadiazole derivatives

  摘要：

  A series of pyrazole-based 1,3,4-oxadiazole derivatives were rationally designed and synthesized in good yields by following a convenient route. All the newly synthesized molecules were fully characterized by IR, H-1 NMR and elemental analysis. Eight compounds were structurally determined by single crystal Xray diffraction analysis. The fluorescence properties of all the compounds were investigated in dimethyl sulfoxide media. In addition, these newly synthesized compounds were evaluated for in vitro inhibitory activity against commercial enzyme xanthine oxidase (XO) by measuring the formation of uric acid from xanthine. Among the compounds synthesized and tested, 3d and 3e were found to be moderate inhibitory activity against commercial XO with IC50 = 72.4 mu M and 75.6 mu M. The studies gave a new insight in further optimization of pyrazole-based 1,3,4-oxadiazole derivatives with excellent fluorescence properties and XO inhibitory activity. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.07.067
• 作为产物：
  描述：

  ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 以93%的产率得到1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide
  参考文献：
  名称：

  新型，取代的吡唑基1,3,4-恶二唑衍生物的合成，表征和光学性质

  摘要：

  在氧氯化磷存在下，通过取代的吡唑-5-碳酰肼与取代的苯甲酸反应，合成了一系列新型的取代的吡唑基1,3,4-恶二唑衍生物。使用IR，1 H NMR和HRMS以及X射线衍射分析对化合物进行表征。在二氯甲烷中研究了化合物的吸收和荧光特性。这些化合物显示相似的吸收，范围为267至281 nm，在〜275 nm处出现很强的吸收带。吡唑基1,3,4-恶二唑衍生物的吸收光谱和荧光特性与对苯环的取代作用的相关性表明，连接在苯环上的甲氧基和溴基团显着影响最大发射。

  DOI：

  10.1016/j.dyepig.2009.11.003

文献信息

• 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, Crystal Structures, Fluorescence and Xanthine Oxidase Inhibitory of Sulfur-Containing Pyrazole Derivatives Incorporated with Oxadiazole and Triazole
  作者：De-Qiang Qi、Chuan-Ming Yu、Jin-Zong You、Guang-Hui Yang、Xue-Jie Wang、Yi-Ping Zhang

  DOI：10.1080/10426507.2015.1085047

  日期：2016.1.2

  GRAPHICAL ABSTRACT Abstract Some sulfur-containing pyrazole derivatives incorporated with 1,3,4-oxadiazole and 1,2,4-triazole were designed and synthesized. All the compounds were fully characterized by IR, 1H NMR, 13C NMR and elemental analyses. Two crystal structures were determined by single crystal X-ray diffraction analyses. The fluorescence properties were investigated in DMSO solution. In addition

  图形摘要摘要设计并合成了一些与1,3,4-恶二唑和1,2,4-三唑结合的含硫吡唑衍生物。所有化合物均通过 IR、1H NMR、13C NMR 和元素分析进行​​了充分表征。通过单晶X射线衍射分析确定了两种晶体结构。在DMSO溶液中研究了荧光性质。此外，还评估了体外黄嘌呤氧化酶 (XO) 抑制活性，结果表明一种化合物显示出中等的 XO 抑制活性。
• The synthesis, characterization and optical properties of novel 5-(3-aryl-1H-pyrazol-5-yl)-2-(3-butyl-1-chloroimidazo[1,5-a]pyridin-7-yl)-1,3,4-oxadiazole
  作者：Yan Qing Ge、Jiong Jia、Teng Wang、Hong Wei Sun、Gui Yun Duan、Jian Wu Wang

  DOI：10.1016/j.saa.2013.12.016

  日期：2014.4

  A series of novel 5-(3-aryl-1H-pyrazol-5-yl)-2-(3-butyl-1-chloroimidazo[1,5-a]- pyridin-7-yl)-1,3,4-oxadiazole derivatives has been synthesized from 3-butyl-1-chloroimidazo[1,5-a]pyridine-7-carboxylic acid and ethyl 3-aryl-1H-pyrazole-5-carboxylate. The compounds were characterized using IR, H-1 NMR, HRMS and UV vis absorption. The fluorescence spectral characteristics of the compounds in dichloromethane were investigated. The results showed that absorption lambda(max) and emission lambda(max) was less correlated with substituent groups on N-1 position of pyrazole moiety and para position of benzene moiety. The calculated molecular orbital correlates well with their absorption. (C) 2013 Elsevier B.V. All rights reserved.
• Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells
  作者：Yong Xia、Chuan-Dong Fan、Bao-Xiang Zhao、Jing Zhao、Dong-Soo Shin、Jun-Ying Miao

  DOI：10.1016/j.ejmech.2008.01.021

  日期：2008.11

  A series of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives were synthesized and the effects of all the compounds on A549 cell growth were investigated. The results showed that all compounds had almost inhibitory effects on the growth of A549 cells. The study on structure-activity relationships and prediction of lipophilicities of compounds showed that compounds with Log P values in the range of 4.12-6.80 had inhibitory effects on the growth of A549 cells, and among of them the hydrazone derived from salicylaldehyde had much more inhibitory effects. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells
  作者：Yong Xia、Zhi-Wu Dong、Bao-Xiang Zhao、Xiao Ge、Ning Meng、Dong-Soo Shin、Jun-Ying Miao

  DOI：10.1016/j.bmc.2007.08.021

  日期：2007.11

  A series of novel 1-arylmethyl-3-aryl- 1 H-pyrazole-5-carbohydrazide derivatives were synthesized, and the effects of all the compounds on A549 cell growth were investigated. The results showed that all the nine compounds had inhibitory effects on the growth of A549 cells and induced the cell apoptosis. The study on Structure-activity relationships and prediction of lipophilicities Of compounds showed that compounds with log P values in the range of 3.12-4.94 had more inhibitory effects oil the growth of A549 cells. (C) 2007 Elsevier Ltd. All rights reserved.