methyl 1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carboxylate | 93618-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carboxylate
• 英文别名: Methyl 1-methyl-3-(4-trifluoromethylphenyl)pyrazole-5-carboxylate；methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]pyrazole-3-carboxylate
• CAS: 93618-49-6
• 化学式: C₁₃H₁₁F₃N₂O₂
• 分子量: 284.238
• InChiKey: HSAFOODLXXARLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbohydrazide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety as cytotoxic agents

  摘要：

  On account of the reported anticancer activity of pyrazoles and oxadiazoles, we have designed and synthesized a novel combinatorial library of S-substituted-1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety and tested for in-vitro cytotoxic activity by MTT assay. Amongst the tested compounds, the compound 5e was the most promising anticancer agent with IC50 value of 15.54 mu M in MCF-7 cells, compared to Doxorubicin as standard drug. The newly synthesized compounds were characterized by NOE, IR, H-1 NMR, C-13 NMR and LC-MS analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.056
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 methyl 1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety as cytotoxic agents

  摘要：

  On account of the reported anticancer activity of pyrazoles and oxadiazoles, we have designed and synthesized a novel combinatorial library of S-substituted-1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety and tested for in-vitro cytotoxic activity by MTT assay. Amongst the tested compounds, the compound 5e was the most promising anticancer agent with IC50 value of 15.54 mu M in MCF-7 cells, compared to Doxorubicin as standard drug. The newly synthesized compounds were characterized by NOE, IR, H-1 NMR, C-13 NMR and LC-MS analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.056

文献信息

• Synthesis, Characterization and Biological Evaluation of a Novel Series of 1,2,4-Triazolo-[3,4-<i>b</i>]-1,3,4-thiadiazines Containing an Amide Linkage
  作者：Pushpan Puthiyapurayil、Boja Poojary、Sunil Kumar Buridipad

  DOI：10.1002/jhet.1766

  日期：2014.8

  Two series of combinatorial library of 3,6-disubstituted-7H-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazines bearing an amide linkage were synthesized. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their cytotoxicity, anti-inflammatory, and analgesic activities. Among the tested compounds, the compound (Ar = 4-(methoxybenzyl)piperazine)

  合成了两个带有酰胺键的3,6-二取代-7 H -1,2,4-三唑-[3,4- b ] -1,3,4-噻二嗪组合库。所有新合成的化合物都通过光谱分析进行了表征。筛选新合成的化合物的细胞毒性，抗炎和止痛活性。在测试的化合物中，该化合物（Ar = 4-（甲氧基苄基）哌嗪）是最有前途的分子，在（MCF-7）细胞中最大抑制浓度（IC 50）值的一半为14.24μM。化合物 （Ar = 4-（氯苄基）哌嗪）， ， 和 （Ar  =  2-（氟苯基）哌嗪）在50 mg / kg的剂量水平下表现出出色的抗炎活性，几乎与标准药物相当。如果被测化合物具有镇痛作用，则这些化合物， ， 和 在100和200 mg / kg / po剂量下均显示出更有效和一致的活性，而致溃疡的风险较小。
• halogen-substituted compounds
  申请人：Maue Michael

  公开号：US20110301181A1

  公开（公告）日：2011-12-08

  The invention relates to compounds of the general formula (I), in which the radicals A 1 , A 2 , A 3 , A 4 , Lm, Q, R 1 , T and U have the meaning given in the description and to the use of the compounds for controlling animal pests. In addition, the invention relates to processes and intermediates for the preparation of the compounds according to formula (I).

  该发明涉及一般式(I)的化合物，其中基团A1、A2、A3、A4、Lm、Q、R1、T和U的含义如描述中所示，以及该化合物用于控制动物害虫。此外，该发明涉及根据一般式(I)制备化合物的工艺和中间体。
• Xanthine oxidase inhibiting
  申请人：Eli Lilly and Company

  公开号：US04495195A1

  公开（公告）日：1985-01-22

  Aryl pyrazole carboxylic acids and derivatives thereof, are xanthine oxidase inhibitors in vivo.

  芳基吡唑羧酸及其衍生物在体内是黄嘌呤氧化酶抑制剂。
• Halogen-substituted compounds
  申请人：Maue Michael

  公开号：US08946234B2

  公开（公告）日：2015-02-03

  The invention relates to compounds of the general formula (I), in which the radicals A1, A2, A3, A4, Lm, Q, R1, T and U have the meaning given in the description and to the use of the compounds for controlling animal pests. In addition, the invention relates to processes and intermediates for the preparation of the compounds according to formula (I).

  本发明涉及通式（I）的化合物，其中基团A1、A2、A3、A4、Lm、Q、R1、T和U的含义如描述中所给，并且涉及将该化合物用于控制动物害虫。此外，本发明还涉及用于制备通式（I）化合物的过程和中间体。
• Novel halogen-substituted compounds
  申请人：Bayer CropScience AG

  公开号：US20150099766A1

  公开（公告）日：2015-04-09

  The invention relates to compounds of the general formula (I), in which the radicals A 1 , A 2 , A 3 , A 4 , Lm, Q, R 1 , T and U have the meaning given in the description and to the use of the compounds for controlling animal pests. In addition, the invention relates to processes and intermediates for the preparation of the compounds according to formula (I).

  本发明涉及一般式（I）的化合物，其中基团A1，A2，A3，A4，Lm，Q，R1，T和U的含义如说明书中所述，并且涉及使用这些化合物来控制动物害虫。此外，本发明还涉及制备公式（I）化合物的过程和中间体。