2-(4-((benzo[d]thiazol-2-yl(pyrimidin-2-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-(trifluoromethoxy)benzyl)acetamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-((benzo[d]thiazol-2-yl(pyrimidin-2-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-(trifluoromethoxy)benzyl)acetamide
• 英文别名: 2-[4-[[1,3-benzothiazol-2-yl(pyrimidin-2-yl)amino]methyl]triazol-1-yl]-N-[[4-(trifluoromethoxy)phenyl]methyl]acetamide
• 化学式: C₂₄H₁₉F₃N₈O₂S
• 分子量: 540.528
• InChiKey: AFAXDSBSWQIXIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-phenyl-N'-(2-pyrimidyl)thiocarbamide 在 copper(l) iodide 、 1,3-dibutyl-2-methylimidazolium bromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-(4-((benzo[d]thiazol-2-yl(pyrimidin-2-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-(trifluoromethoxy)benzyl)acetamide
  参考文献：
  名称：

  Synthesis and anticancer evaluation of novel triazole linked N-(pyrimidin-2-yl)benzo[d]thiazol-2-amine derivatives as inhibitors of cell survival proteins and inducers of apoptosis in MCF-7 breast cancer cells

  摘要：

  A series of novel triazole linked N-(pyrimidin-2yl)benzo[d]thiazol-2-amine 5a-k were synthesized and evaluated for anticancer activity against breast (MCF-7), lung (A549) and skin (A375) cancer cell lines and their cytotoxic effects were compared against normal breast epithelial cells. The effect of compounds on cell cycle of MCF-7 breast cancer cell line was investigated by FACS. Result indicated G2/M cell cycle arrest of MCF-7 cells. Further promising compounds 5b, 5g, 5h and 5i were tested for their apoptosis inducing ability as well as inhibitory activity against key proteins NF-kB, Survivin, CYP1A1, and ERK1/2 which help in cancer cell survival and proliferation. The apoptotic aspect of these compounds is further evidenced by increase in the activity of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in highly malignant breast cancers and can be selected for further biological studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.083

文献信息

• Synthesis and anticancer evaluation of novel triazole linked N-(pyrimidin-2-yl)benzo[d]thiazol-2-amine derivatives as inhibitors of cell survival proteins and inducers of apoptosis in MCF-7 breast cancer cells
  作者：Ravindra M. Kumbhare、Tulshiram L. Dadmal、M. Janaki Ramaiah、K.S.V. Kishore、S.N.C.V.L. Pushpa Valli、Sudheer Kumar Tiwari、K. Appalanaidu、Y. Khageswar Rao、Manika pal Bhadra

  DOI：10.1016/j.bmcl.2014.11.083

  日期：2015.2

  A series of novel triazole linked N-(pyrimidin-2yl)benzo[d]thiazol-2-amine 5a-k were synthesized and evaluated for anticancer activity against breast (MCF-7), lung (A549) and skin (A375) cancer cell lines and their cytotoxic effects were compared against normal breast epithelial cells. The effect of compounds on cell cycle of MCF-7 breast cancer cell line was investigated by FACS. Result indicated G2/M cell cycle arrest of MCF-7 cells. Further promising compounds 5b, 5g, 5h and 5i were tested for their apoptosis inducing ability as well as inhibitory activity against key proteins NF-kB, Survivin, CYP1A1, and ERK1/2 which help in cancer cell survival and proliferation. The apoptotic aspect of these compounds is further evidenced by increase in the activity of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in highly malignant breast cancers and can be selected for further biological studies. (C) 2014 Elsevier Ltd. All rights reserved.