Ethyl 1-(4-bromophenyl)-4-[5-methyl-1-phenyl-3-(phenylcarbamoyl)pyrazole-4-carbonyl]pyrazole-3-carboxylate | 1015757-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 1-(4-bromophenyl)-4-[5-methyl-1-phenyl-3-(phenylcarbamoyl)pyrazole-4-carbonyl]pyrazole-3-carboxylate
• CAS: 1015757-40-0
• 化学式: C₃₀H₂₄BrN₅O₄
• 分子量: 598.456
• InChiKey: KNMKKZRBEBMYHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-[(E)-3-(dimethylamino)prop-2-enoyl]-5-methyl-N,1-diphenylpyrazole-3-carboxamide 、 ethyl (Z)-2-chloro-2-(2-(4-bromophenyl)hydrazono)acetate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 以71%的产率得到Ethyl 1-(4-bromophenyl)-4-[5-methyl-1-phenyl-3-(phenylcarbamoyl)pyrazole-4-carbonyl]pyrazole-3-carboxylate
  参考文献：
  名称：

  Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives

  摘要：

  The versatile, hitherto unreported 4-acetyl-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) was prepared via the reaction of 2-(2-phenylhydrazono)-2-chloro-N-phenylacetamide with pentan-2,4-dione in the presence of sodium ethoxide. Reaction of 3 with dimethylformamide-dimethylacetal (DMF-DMA) furnished the corresponding 4-[(E)-3-(dimethylamino)aci-yloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (5). The latter product underwent regioselective 1,3-dipolar cycloaddition with some nitrilimines to afford the non-isolable dihydropyrazole intermediates which then lose dimethylamine yielding the corresponding pyrazole derivatives. The preliminary screening for the antitumor activity of all newly synthesized compounds was carried out against Ehrlich Ascites Carcinoma tumor cells. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.015