5-(3-Fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde | 109925-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3-Fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde
• CAS: 109925-16-8
• 化学式: C₁₂H₁₁FN₂O₂
• mdl: MFCD11191325
• 分子量: 234.23
• InChiKey: CCANDPULTCWVLP-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde 在 盐酸羟胺 、 potassium carbonate 、 caesium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  新型含恶唑环的吡唑肟衍生物的合成及生物活性

  摘要：

  设计合成了一系列新型的含恶唑环的吡唑肟衍生物。通过1 H NMR，13 C NMR光谱和元素分析在结构上确认标题化合物。初步的生物测定结果表明，某些标题化合物除具有杀虫和杀螨活性外，还显示出有希望的杀真菌活性。特别地，化合物8c对黄瓜假单胞菌孢子菌表现出强效的杀真菌活性，而对黄瓜蚜虫和褐飞虱具有良好的杀虫活性。

  DOI：

  10.1016/j.cclet.2015.04.017
• 作为产物：
  描述：

  1,3-二甲基-5-吡唑酮 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 5-(3-Fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde
  参考文献：
  名称：

  Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids

  摘要：

  A series of hybrids 10a-v based on coumarin/pyrazole oxime have been synthesized, and exhibit good to excellent antitumor activities. Compound 10n has shown remarkable anticancer effect on SMMC-7721 cells (IC50 = 2.08 mu M), which is considerably lower than 5-FU (IC50 = 37.8 mu M) and similar to ADM (IC50 = 2.67 mu M), with little effect on normal hepatic cells LO2. Notably, the suppression experiments of metastatic activities reveal that 10n also displays significant anti-metastasis effects through inhibiting cell migration and invasion in highly metastatic SMMC-7721 cell line, and dose-dependently reverses TGF-beta 1-induced epithelial-mesenchymal transition (EMT) procedure better than ADM. Finally, 10n also possesses low acute toxicity and potent tumor growth inhibitory property against SMMC-7721 cell lines in vivo. Our findings suggest that novel coumarin/pyrazole oxime hybrids are promising therapeutic agent candidates for further research. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.01.070

文献信息

• Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives
  作者：Hong Dai、Linyu Ye、Huiyang Zhuang、Baojiang Dai、Yuan Fang、Yujun Shi

  DOI：10.3390/molecules201219811

  日期：——

  In this study, in order to find novel biologically active pyrazole oxime compounds, a number of dichloro-allyloxy-phenol-containing pyrazole oximes were designed and synthesized according to the method of active group combination. All of the target compounds were confirmed by 1H-NMR, 13C-NMR and elemental analysis. In addition, bioassays showed that all of the newly synthesized compounds had no acaricidal activity against Tetranychus cinnabarinus and low insecticidal activity against Aphis craccivora at tested concentrations. However, most of them displayed excellent insecticidal activity against Oriental armyworm at a concentration of 500 μg/mL, and some designed compounds still exhibited potent insecticidal activity against Oriental armyworm even at the dose of 20 μg/mL, especially compounds 7f, 7n and 7p had 100%, 90% and 90% inhibition rates, respectively, which were comparable to that of the control pyridalyl.

  在本研究中，为了寻找新型生物活性吡唑肟化合物，根据活性基团组合的方法设计并合成了多种含有二氯烯丙氧基苯酚的吡唑肟类化合物。所有目标化合物均通过1H-NMR、13C-NMR和元素分析得到确认。此外，生物测定显示，所有新合成的化合物对朱砂叶螨无杀螨活性，对豌豆蚜的杀虫活性较低（测试浓度下）。然而，它们大多数在500 μg/mL浓度下对东方粘虫显示出优异的杀虫活性，其中某些设计化合物甚至在20 μg/mL剂量下仍对东方粘虫表现出强效的杀虫活性，特别是化合物7f、7n和7p分别达到了100%、90%和90%的抑制率，这些结果与对照化合物pyridalyl相媲美。
• Design, Synthesis, and Biological Activities of Novel Pyrazole Oxime Compounds Containing a Substituted Pyridyl Moiety
  作者：Cuili Chen、Jia Chen、Haiying Gu、Ning Bao、Hong Dai

  DOI：10.3390/molecules22060878

  日期：——

  In this paper, in order to find novel biologically active pyrazole oximes, a series of pyrazole oxime compounds bearing a substituted pyridyl unit were prepared. Bioassays showed that some target compounds were found to have good acaricidal activity against Tetranychus cinnabarinus at a concentration of 500 μg/mL, compound 9q especially displayed potent acaricidal activity against T. cinnabarinus when

  在本文中，为了找到新颖的生物活性吡唑肟，制备了一系列带有取代吡啶基单元的吡唑肟化合物。生物测定法显示，发现一些目标化合物在500μg/ mL的浓度下对朱砂叶螨有良好的杀螨活性，化合物9q在浓度降低至100μg/ mL时尤其显示出对朱砂叶螨的强杀螨活性。有趣的是，大多数目标化合物以500μg/ mL的浓度具有出色的对东方粘虫的杀虫活性。此外，某些化合物对500 mg / mL的抗蚜虫和褐飞虱具有活性。此外，化合物9b，9g，9l，9p，9q，9r，9s，9t，9u和9v对HepG2细胞显示出显着的抗增殖活性，IC50值为1.53-17.27μM，
• Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety
  作者：Hong Dai、Jia Chen、Hong Li、Baojiang Dai、Haibing He、Yuan Fang、Yujun Shi

  DOI：10.3390/molecules21030276

  日期：——

  in order to find novel biologically active pyrazole oxime compounds, a series of pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety were synthesized. Preliminary bioassays indicated that most title compounds were found to display good to excellent acaricidal activity against Tetranychus cinnabarinus at a concentration of 200 μg/mL, and some designed compounds still showed excellent

  在这项研究中，为了找到新型的具有生物活性的吡唑肟化合物，合成了一系列含有5-三氟甲基吡啶基部分的吡唑肟衍生物。初步的生物分析表明，发现大多数标题化合物在200μg/ mL的浓度下对朱砂叶螨具有良好的杀螨活性，而某些设计的化合物在10μg/ mL的浓度下仍对朱砂叶螨具有优良的杀螨活性。因为化合物8e，8f，8l，8m，8n，8p和8q的抑制率均为100.00％。有趣的是，一些目标化合物在200μg/ mL的浓度下对小菜蛾和蚜虫具有中等至良好的杀虫活性。此外，
• Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 1,2,3-thiadiazole moiety
  作者：Hong Dai、Shushan Ge、Gang Li、Jia Chen、Yujun Shi、Linyu Ye、Yong Ling

  DOI：10.1016/j.bmcl.2016.07.068

  日期：2016.9

  A series of new pyrazole oxime compounds bearing a 1,2,3-thiadiazole ring were designed, synthesized, and evaluated for their insecticidal, acaricidal and antitumor activities. Bioassays demonstrated that some title compounds displayed satisfactory insecticidal and acaricidal properties. Especially, compounds 8d and 8h exhibited 90% insecticidal activities against Aphis craccivora at the concentration

  设计，合成了一系列带有1,2,3-噻二唑环的新型吡唑肟化合物，并对其杀虫，杀螨和抗肿瘤活性进行了评估。生物测定表明，某些标题化合物具有令人满意的杀虫和杀螨特性。特别地，化合物8d和8h在100μg/ mL的浓度下表现出对蟹蚜的90％的杀虫活性。有趣的是，某些目标化合物在体外具有对四种人类癌细胞系的显着抗肿瘤活性。其中，化合物8e（IC50 =7.19μM），化合物8l（IC50 =6.56μM），化合物8m（IC50 =8.12μM）和化合物8r（IC50 =7.06μM）对HCT-116细胞的抑制作用均优于对照物5-氟尿嘧啶（IC50 =29.50μM）。此外，化合物8j，8m，
• Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives
  作者：Hong Dai、Gang Li、Jia Chen、Yujun Shi、Shushan Ge、Chongguang Fan、Haibing He

  DOI：10.1016/j.bmcl.2016.04.094

  日期：2016.8

  4-thiadiazole-containing pyrazole oximes was designed and synthesized. Their acaricidal and insecticidal activities were evaluated. Bioassay results indicated that some target compounds exhibited good acaricidal and insecticidal properties. Especially, compound 8m had 80% acaricidal activity against Tetranychus cinnabarinus at the concentration of 50 μg/mL, compound 8f displayed 100% insecticidal activities against

  设计并合成了一个新的含1,3,4-噻二唑的吡唑肟库。他们的杀螨和杀虫活性进行了评估。生物测定结果表明，某些目标化合物具有良好的杀螨和杀虫特性。尤其是，化合物8m在浓度为50μg/ mL时对朱砂叶螨有80％的杀螨活性，化合物8f在浓度为50μg/ mL时对蟹蚜有100％的杀虫活性，化合物8r和8w对蚜虫有100％的杀虫活性。小菜蛾的浓度为50μg/ mL。此外，化合物8r（LC50  = 19.61微克/毫升）和8瓦特（LC 50  = 9.78微克/毫升）具有可比较的或甚至更好的杀虫活性比对照Pyridalyl（LC 50  = 17.40微克/毫升）对小菜蛾。