tert-butyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-methylthio)carbonothioyl)piperazine-1-carboxylate | 1430852-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-methylthio)carbonothioyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[[1-[(2-chlorophenyl)methyl]triazol-4-yl]methylsulfanylcarbothioyl]piperazine-1-carboxylate；tert-butyl 4-[[1-[(2-chlorophenyl)methyl]triazol-4-yl]methylsulfanylcarbothioyl]piperazine-1-carboxylate
• CAS: 1430852-47-3
• 化学式: C₂₀H₂₆ClN₅O₂S₂
• 分子量: 468.044
• InChiKey: WMWXVNAFOVFWIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-methylthio)carbonothioyl)piperazine-1-carboxylate 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents

  摘要：

  A series of novel 1,2,3-triazole-dithiocarbamate hybrids were designed, synthesized and evaluated for anticancer activity against four selected human tumor cell lines (MGC-803, MCF-7, PC-3, EC-109). Majority of the synthesized compounds exhibited moderate to potent activity against MGC-803 and MCF-7. Among them, compounds 3a and 3c showed excellent broad spectrum anticancer activity with IC50 values ranging from 0.73 to 11.61 mu M and 0.49-12.45 mu M, respectively. Particularly, compound 3a was more potent than 5-fluorouracil against all tested human cancer cell lines. Flow cytometry analysis demonstrated that treatment of MGC-803 with 3c led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death after 12 h. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.046
• 作为产物：
  描述：

  N-Boc-哌嗪 在 sodium phosphate dodecahydrate 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 tert-butyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-methylthio)carbonothioyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Triazole–Dithiocarbamate Based Selective Lysine Specific Demethylase 1 (LSD1) Inactivators Inhibit Gastric Cancer Cell Growth, Invasion, and Migration

  摘要：

  Lysine specific demethylase 1 (LSD1), the first identified histone demethylase, plays an important role in epigenetic regulation of gene activation and repression. The up-regulated LSD l's expression has been reported in several malignant tumors. In the current study, we designed and synthesized five series of 1,2,3-triazole-dithiocarbamate hybrids and screened their inhibitory activity toward LSD1. We found that some of these compounds, especially compound 26, exhibited the most specific and robust inhibition of LSD1. Interestingly, compound 26 also showed potent and selective cytotoxicity against LSD1 overexpressing gastric cancer cell lines MGC-803 and HGC-27, as well as marked inhibition of cell migration and invasion, compared to 2-PCPA. Furthermore, compound 26 effectively reduced the tumor growth bared by human gastric cancer cells in vivo with no signs of adverse side effects. These findings suggested that compound 26 deserves further investigation as a lead compound in the treatment of LSD1 overexpressing gastric cancer.

  DOI：

  10.1021/jm401002r