2-[(4-Tert-butylphenyl)methyl]-5-phenylpyrazole-3-carbohydrazide | 955084-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(4-Tert-butylphenyl)methyl]-5-phenylpyrazole-3-carbohydrazide
• CAS: 955084-65-8
• 化学式: C₂₁H₂₄N₄O
• 分子量: 348.448
• InChiKey: WLTLIURVOWJWDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 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：

  2-[(4-Tert-butylphenyl)methyl]-5-phenylpyrazole-3-carbohydrazide 、 2-羟基-5-甲基苯乙酮 以 乙醇 为溶剂， 以84%的产率得到(E)-1-(4-tert-butylbenzyl)-N'-(1-(2-hydroxy-5-methylphenyl)ethylidene)-3-phenyl-1H-pyrazole-5-carbohydrazide
  参考文献：
  名称：

  新型取代的吡唑-5-碳酰肼衍生物的合成及在A549肺癌细胞中强凋亡诱导剂的发现

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2009.01.037
• 作为产物：
  描述：

  Ethyl 2-[(4-tert-butylphenyl)methyl]-5-phenylpyrazole-3-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 以76%的产率得到2-[(4-Tert-butylphenyl)methyl]-5-phenylpyrazole-3-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 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.
• 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.
• 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 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。