ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate | 618070-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 2-benzyl-5-phenylpyrazole-3-carboxylate
• CAS: 618070-52-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: NALCDGDGLJAMQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate 在 肼 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(3-butyl-1-chloroimidazo[1,5-a]pyridin-7-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.saa.2013.12.016
• 作为产物：
  描述：

  苯乙酮 在 sodium ethanolate 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  一种吡唑衍生物及其在制备抗肿瘤药物方面的应用

  摘要：

  本发明属于药物化学领域，具体公开了一种吡唑衍生物及其在制备抗肿瘤药物方面的应用。本发明以不同取代基的苯乙酮为原料，经克莱森缩合，关环，再经取代，水解反应，酰胺偶联反应最终得到一系列新的吡唑类衍生物。本发明通过四氮唑盐还原法(MTT)对新化合物进行抗癌活性测试，结果显示合成的一系列吡唑类衍生物具有较好的抗癌活性。

  公开号：

  CN114057646B

文献信息

• Divergent synthesis of 1,3,5-tri and 1,3-disubstituted pyrazoles under transition metal-free conditions
  作者：Liyao Ma、Pengcheng Ou、Xueliang Huang

  DOI：10.1039/d0ob01478h

  日期：——

  Pyrazole cores are common structural motifs existing in various agrochemicals and pharmaceuticals. Herein, a transition metal-free, three-component reaction of arylaldehydes, ethyl acrylate and N-tosylhydrazones is described, which leads to the formation of 1,3,5-trisubstituted and 1,3-disubstituted pyrazoles divergently under slightly different conditions.

  吡唑核心是存在于各种农用化学品和药物中的常见结构基序。本文描述了芳醛、丙烯酸乙酯和N-甲苯磺酰腙的无过渡金属的三组分反应，该反应导致在稍有不同的条件下不同地形成 1,3,5-三取代和 1,3-二取代吡唑。
• 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。
• Biological activities of novel pyrazolyl hydroxamic acid derivatives against human lung cancer cell line A549
  作者：Jin-Feng Zhang、Meng Li、Jun-Ying Miao、Bao-Xiang Zhao

  DOI：10.1016/j.ejmech.2014.06.065

  日期：2014.8

  We synthesized a series of novel pyrazolyl hydroxamic acid derivatives (4a–4l) and investigated their biological activities against human lung cancer cell line A549 in vitro to determine their mechanism of action. The results showed that the majority of derivatives had inhibitory effects on the growth of A549 cancer cells in dose and time-dependent manners, in which the compounds 4b, 4f, 4h and 4j

  我们合成了一系列新型的吡唑基异羟肟酸衍生物（4a - 4l），并在体外研究了它们对人肺癌细胞A549的生物学活性，以确定它们的作用机理。结果表明，大多数衍生物对A549癌细胞的生长具有剂量和时间依赖性的抑制作用，其中化合物4b，4f，4h和4j（10μM）具有更有效的抗增殖活性。但是，应注意4j可能导致10μM坏死。此外，三种化合物4b，4f和4h诱导细胞周期阻滞于G1期并触发自噬，但在刺激条件下不能明显诱导细胞凋亡和坏死。因此，吡唑基异羟肟酸衍生物4b，4f和4h可用于研究自噬的调节机制，并为预防肺癌提供新的方法。
• 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.