3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbohydrazide | 955084-68-1

• 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-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbohydrazide
• 英文别名: 2-[(4-Tert-butylphenyl)methyl]-5-(4-chlorophenyl)pyrazole-3-carbohydrazide
• CAS: 955084-68-1
• 化学式: C₂₁H₂₃ClN₄O
• 分子量: 382.893
• InChiKey: FXZNIPCWQRUALX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbohydrazide 在 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.33h， 生成 2-(1-(4-(tert-butyl)benzyl)-3-(4-chlorophenyl)-1H-pyrazol-5-yl)-5-((4-chlorophenoxy)methyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, X-Ray Crystal Structures and Optical Properties of Novel Substituted Pyrazoly 1,3,4-Oxadiazole Derivatives

  摘要：

  合成了新型吡唑-1,3,4-恶二唑衍生物，并通过 1H NMR、IR、HRMS 和 X 射线衍射分析对其进行了表征。这些化合物在不同溶液中的紫外-可见吸收和荧光性质表明，其最大吸收波长在不同溶剂中没有显著变化；然而，最大发射波长随溶剂极性的增加而红移。吸收 λmax 和发射 λmax 与芳基环上的取代基团的相关性较小。

  DOI：

  10.1007/s10895-011-0874-7
• 作为产物：
  描述：

  对叔丁基氯苄 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological validation of novel pyrazole derivatives with anticancer activity guided by 3D-QSAR analysis

  摘要：

  Using literature data on anticancer activity of pyrazole derivatives, 3D-QSAR models were developed and 3D-QSAR analysis was performed. The 3D-QSAR analysis enabled identification of molecular properties that have the highest impact on antitumor activity against lung cancer cells. The results of 3D-QSAR analysis were taken into account while new compounds were designed. Obtained 3D-QSAR models were used for prediction of activity of new compounds. In this way, design of new compounds was guided by 3D-QSAR analysis which was performed on literature data. Ten new pyrazole derivatives were synthesised and their antitumor activities against A549 and NCIH23 lung cancer cells were validated. In order to obtain full profile of anticancer activity, cells viability (MTS) assays were combined with cell proliferation (BrdU) assays which measure actively dividing cells in treated sample. Experimental measurements showed good agreement between predicted and measured activities for majority of compounds. Also, anticancer activities of new pyrazole derivatives pointed to the chemical groups that can be useful in designing antitumor molecules. Substitution of hydrazine linker with rigid, 1,2,4-oxadiazole moiety resulted in compound 10, which has low (if any) cytotoxic activity and high potential cytostatic activity. Therefore, compound 10 presents a good starting point for design of new, more potent and safer anticancer therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.032

文献信息

• The synthesis, characterization and optical properties of novel, substituted, pyrazoly 1,3,4-oxadiazole derivatives
  作者：Hong-Shui Lv、Bao-Xiang Zhao、Ji-Kun Li、Yong Xia、Song Lian、Wei-Yong Liu、Zhong-Liang Gong

  DOI：10.1016/j.dyepig.2009.11.003

  日期：2010.6

  A series of novel substituted pyrazoly 1,3,4-oxadiazole derivatives were synthesized by the reaction of substituted pyrazole-5-carbohydrazide with substituted benzoic acid in the presence of phosphorus oxychloride. The compounds were characterised using IR, 1H NMR and HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane

  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。
• 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 of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells
  作者：Liang-Wen Zheng、Ling-Ling Wu、Bao-Xiang Zhao、Wen-Liang Dong、Jun-Ying Miao

  DOI：10.1016/j.bmc.2009.01.037

  日期：2009.3

  compounds on A549 cell growth were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound (E)-1-(4-tert-butylbenzyl)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide (3e) possessed the highest growth inhibitory effect and induced apoptosis of A549 lung cancer cells.

  一系列新的3-芳基-1-（4-叔丁基苄基）- 1 H ^吡唑-5-碳酰肼腙衍生物的合成和研究了所有对A549细胞生长的化合物的作用。结果表明，所有化合物均对A549肺癌细胞和化合物（E）-1-（4-叔丁基苄基）-N '-（1-（5-氯-2-羟苯基）亚乙基）有抑制作用。-3-（4-氯苯基）-1 H-吡唑-5-碳酰肼（3e）具有最高的生长抑制作用，并诱导了A549肺癌细胞的凋亡。
• 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 discovery of pyrazole-5-carbohydrazide N-glycosides as inducer of autophagy in A549 lung cancer cells
  作者：Song Lian、Hua Su、Bao-Xiang Zhao、Wei-Yong Liu、Liang-Wen Zheng、Jun-Ying Miao

  DOI：10.1016/j.bmc.2009.09.004

  日期：2009.10

  A series of novel 3-aryl-1-arylmethyl-1H-pyrazole-5-carbohydrazide N-beta-glycoside derivatives was synthesized by the reaction of substituted 1H-pyrazole-5-carbohydrazide with D-sugar and the effects of all the compounds on A549 cell growth were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 3d possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.