N-((5-(4-fluorophenyl)-1,3,4-oxadiazole-2-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide | 1543025-05-3

• 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: N-((5-(4-fluorophenyl)-1,3,4-oxadiazole-2-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide
• 英文别名: N-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methyl]-4-(trifluoromethyl)benzenesulfonamide
• CAS: 1543025-05-3
• 化学式: C₁₆H₁₁F₄N₃O₃S
• 分子量: 401.341
• InChiKey: OAGJXRNBDDVNCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-(2-hydrazinyl-2-oxoethyl)-4-(trifluoromethyl)benzenesulfonamide 在 碘苯二乙酸 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-((5-(4-fluorophenyl)-1,3,4-oxadiazole-2-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative activity of 2,5-disubstituted-1,3,4-oxadiazoles containing trifluoromethyl benzenesulfonamide moiety

  摘要：

  A series of new 2,5-disubstituted-1,3,4-oxadiazoles 6(a-j) have been conveniently synthesized by intermolecular oxidative cyclization of (E)-2-(arylbenzylidene)-2-[(4-methoxyphenyl)amino]acetohydrazides promoted by iodobenzene diacetate as an oxidant. The synthesized compounds were characterized by elemental analyses, FT-IR, LCMS, H-1 NMR, and C-13 NMR spectral studies. All the compounds were evaluated for their in vitro antiproliferative effect using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay method against four human cancer cell lines (K562, Colo-205, MDA-MB 231, IMR-32) for the time period of 24 h. Among the analogs, compounds 6h and 6i showed good activity on all cell lines, whereas the other compounds in the series exhibited moderate activity.

  DOI：

  10.1007/s00044-014-0918-z

文献信息

• Synthesis and in vitro antiproliferative activity of 2,5-disubstituted-1,3,4-oxadiazoles containing trifluoromethyl benzenesulfonamide moiety
  作者：Basavapatna N. Prasanna Kumar、Kikkeri N. Mohana、Lingappa Mallesha、Bantal Veeresh

  DOI：10.1007/s00044-014-0918-z

  日期：2014.7

  A series of new 2,5-disubstituted-1,3,4-oxadiazoles 6(a-j) have been conveniently synthesized by intermolecular oxidative cyclization of (E)-2-(arylbenzylidene)-2-[(4-methoxyphenyl)amino]acetohydrazides promoted by iodobenzene diacetate as an oxidant. The synthesized compounds were characterized by elemental analyses, FT-IR, LCMS, H-1 NMR, and C-13 NMR spectral studies. All the compounds were evaluated for their in vitro antiproliferative effect using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay method against four human cancer cell lines (K562, Colo-205, MDA-MB 231, IMR-32) for the time period of 24 h. Among the analogs, compounds 6h and 6i showed good activity on all cell lines, whereas the other compounds in the series exhibited moderate activity.