1,1,1-trifluoro-8-(3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl)octan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1,1-trifluoro-8-(3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl)octan-2-one
• 英文别名: 1,1,1-Trifluoro-8-[3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl]octan-2-one
• 化学式: C₁₆H₁₆F₃N₃O₄
• 分子量: 371.316
• InChiKey: BOKSHKSNYIKJED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-硝基苄胺肟 在 吡啶 、 草酰氯 、 水 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1,1,1-trifluoro-8-(3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl)octan-2-one
  参考文献：
  名称：

  Discovery, bioactivity and docking simulation of Vorinostat analogues containing 1,2,4-oxadiazole moiety as potent histone deacetylase inhibitors and antitumor agents

  摘要：

  In our study, three series of hydroxamate, 2-aminobenzamide, and trifluoromethyl ketone analogues have been designed and synthesized. The synthesized compounds were investigated for their in vitro antiproliferative activities using the MTT-based assay against three human cancer cell lines including A549, NCI-H661, and U937. Most analogues exhibited higher antiproliferative activities against human acute myeloid leukemia cell U937 than the other two human lung cancer cell lines. Furthermore, the compounds were examined against HDAC1, 2, and 8 isoforms. Docking study of compounds 6h, 9b, and 10a suggested that they might bind tightly to the binding pocket of HDAC2 and/or HDAC8. The results suggest that these compounds might have potential as lead compounds for the development of anti-tumor drugs with HDACs inhibitory activities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.028

文献信息

• Discovery, bioactivity and docking simulation of Vorinostat analogues containing 1,2,4-oxadiazole moiety as potent histone deacetylase inhibitors and antitumor agents
  作者：Jin Cai、Hongtao Wei、Kwon Ho Hong、Xiaoqing Wu、Xi Zong、Meng Cao、Peng Wang、Lushen Li、Chunlong Sun、Bo Chen、Gaoxing Zhou、Junqing Chen、Min Ji

  DOI：10.1016/j.bmc.2015.04.028

  日期：2015.7

  In our study, three series of hydroxamate, 2-aminobenzamide, and trifluoromethyl ketone analogues have been designed and synthesized. The synthesized compounds were investigated for their in vitro antiproliferative activities using the MTT-based assay against three human cancer cell lines including A549, NCI-H661, and U937. Most analogues exhibited higher antiproliferative activities against human acute myeloid leukemia cell U937 than the other two human lung cancer cell lines. Furthermore, the compounds were examined against HDAC1, 2, and 8 isoforms. Docking study of compounds 6h, 9b, and 10a suggested that they might bind tightly to the binding pocket of HDAC2 and/or HDAC8. The results suggest that these compounds might have potential as lead compounds for the development of anti-tumor drugs with HDACs inhibitory activities. (C) 2015 Elsevier Ltd. All rights reserved.