N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}-4-trifluoromethylbenzenesulfonamide

• 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-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}-4-trifluoromethylbenzenesulfonamide
• 英文别名: 2-(4-Trifluoromethyl-benzenesulfonylimino)-imidazolidine-1-c arbodithioic acid 3-thioxo-5,1-c][1,2,4] thiadiazol-7-yl ester；(3-sulfanylidene-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-yl) 2-[[4-(trifluoromethyl)phenyl]sulfonylamino]-4,5-dihydroimidazole-1-carbodithioate
• 化学式: C₁₅H₁₃F₃N₆O₂S₅
• 分子量: 526.632
• InChiKey: HNTAQWPMHHSOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}-4-trifluoromethylbenzenesulfonamide 在 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以64%的产率得到bis{[2-((4-trifluoromethylphenyl)sulfonylimino)imidazolidin-1-yl]thiocarbonyl} disulfide
  参考文献：
  名称：

  Synthesis, X-ray structure analysis and computational studies of novel bis(thiocarbamoyl) disulfides with non-covalent S⋯N and S⋯S interactions

  摘要：

  In this Letter, we describe the synthesis of several bis(thiocarbamoyl) disulfides that present interesting intramolecular S center dot center dot center dot N and S center dot center dot center dot S interactions. In one case, crystals suitable for X-ray characterization have been obtained. The non-covalent interactions have been studied analyzing the crystal structure and by means of high level density functional theory (DFT) calculations (RI-PB86/TZVP) using both 'atoms-in-molecules' (AIM) and natural bond orbital (NBO) analyses. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.02.022
• 作为产物：
  描述：

  4-三氟甲基苯磺酰氯 、 (9ci)-5,6-二氢-1H,3h-咪唑并[2,1-c][1,2,4]噻二唑-3-硫酮 在 吡啶 作用下， 反应 12.0h， 以48%的产率得到N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}-4-trifluoromethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides

  摘要：

  A series of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides (2a-z) was obtained by reacting 6,7-dihydro-1H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione (1) with arylsulfonyl chlorides. The relationships between structure and anti-tumor activity revealed that compound 2o with p-Cl substituent at the phenyl ring was most active (-log GI50 > 8.00, -log TGI = 7.66) and was found to exhibit high selectivity toward the leukemia CCRF-CEM cell line (Delta(f) = 3.08 and 3.31, respectively). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.067

文献信息

• Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides
  作者：Jarosław Sączewski、Zdziaław Brzozowski、Franciszek Sączewski、Patrick J. Bednarski、Manuel Liebeke、Maria Gdaniec

  DOI：10.1016/j.bmcl.2006.04.067

  日期：2006.7

  A series of N-1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides (2a-z) was obtained by reacting 6,7-dihydro-1H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione (1) with arylsulfonyl chlorides. The relationships between structure and anti-tumor activity revealed that compound 2o with p-Cl substituent at the phenyl ring was most active (-log GI50 > 8.00, -log TGI = 7.66) and was found to exhibit high selectivity toward the leukemia CCRF-CEM cell line (Delta(f) = 3.08 and 3.31, respectively). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, X-ray structure analysis and computational studies of novel bis(thiocarbamoyl) disulfides with non-covalent S⋯N and S⋯S interactions
  作者：Jarosław Sączewski、Antonio Frontera、Maria Gdaniec、Zdzisław Brzozowski、Franciszek Sączewski、Piotr Tabin、David Quiñonero、Pere M. Deyà

  DOI：10.1016/j.cplett.2006.02.022

  日期：2006.4

  In this Letter, we describe the synthesis of several bis(thiocarbamoyl) disulfides that present interesting intramolecular S center dot center dot center dot N and S center dot center dot center dot S interactions. In one case, crystals suitable for X-ray characterization have been obtained. The non-covalent interactions have been studied analyzing the crystal structure and by means of high level density functional theory (DFT) calculations (RI-PB86/TZVP) using both 'atoms-in-molecules' (AIM) and natural bond orbital (NBO) analyses. (c) 2006 Elsevier B.V. All rights reserved.