5-(2-Bromophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde | 1152560-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-Bromophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde
• CAS: 1152560-07-0
• 化学式: C₁₂H₁₁BrN₂O₂
• mdl: MFCD11191303
• 分子量: 295.136
• InChiKey: BWZYDTHZNFMXEN-UHFFFAOYSA-N

物化性质

• 沸点：
  370.0±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-Bromophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde 在 盐酸羟胺 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 5-(2-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde O-(4-((2-chlorothiazol-5-yl)methoxy)benzyl) oxime
  参考文献：
  名称：

  The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity

  摘要：

  DOI：

  10.1016/j.cclet.2014.06.011
• 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-(2-Bromophenoxy)-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

• 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，