5-(2,3-Difluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde | 1429415-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,3-Difluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde
• CAS: 1429415-31-5
• 化学式: C₁₂H₁₀F₂N₂O₂
• 分子量: 252.22
• InChiKey: INYGOKDNDMTNHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2,3-Difluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde 在 盐酸羟胺 、 potassium hydroxide 作用下， 生成
  参考文献：
  名称：

  含有5-三氟甲基吡啶基部分的新型吡唑肟衍生物的合成和生物活性。

  摘要：

  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，

  DOI：

  10.3390/molecules21030276
• 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-(2,3-Difluorophenoxy)-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，
• 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，
• 含4-二氟甲基-1,2,3-噻二唑结构的吡唑化合物的制备与应用
  申请人：南通大学

  公开号：CN111646988B

  公开（公告）日：2022-11-01

  本发明涉及含4‑二氟甲基‑1,2,3‑噻二唑结构的吡唑化合物(I)的制备与应用。通过1,3‑二甲基‑5‑芳氧基吡唑‑4‑甲醛(II)与4‑二氟甲基‑1,2,3‑噻二唑‑5‑酰肼(III)的缩合而成。所述含4‑二氟甲基‑1,2,3‑噻二唑结构的吡唑化合物(I)对植物病菌显示出良好的杀菌效果，该化合物可用于制备农业、园艺等领域的杀菌剂。
• Discovery of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as potent agonists of TGR5 via sequential combinatorial libraries
  作者：Allyn T. Londregan、David W. Piotrowski、Kentaro Futatsugi、Joseph S. Warmus、Markus Boehm、Philip A. Carpino、Janice E. Chin、Ann M. Janssen、Nicole S. Roush、Joanne Buxton、Terri Hinchey

  DOI：10.1016/j.bmcl.2012.12.076

  日期：2013.3

  Optimization of a high-throughput screening hit led to the discovery of a new series of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as highly potent agonists of TGR5. This novel chemotype was rapidly developed through iterative combinatorial library synthesis. It was determined that in vitro agonist potency correlated with functional activity data from human peripheral blood monocytes. (c) 2013 Elsevier Ltd. All rights reserved.
• Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids
  作者：Hong Dai、Meiling Huang、Jianqiang Qian、Ji Liu、Chi Meng、Yangyang Li、Guxu Ming、Ting Zhang、Senling Wang、Yujun Shi、Yong Yao、Shushan Ge、Yanan Zhang、Yong Ling

  DOI：10.1016/j.ejmech.2019.01.070

  日期：2019.3

  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.