8-o-Tolyl-2,6,7,8-tetrahydro-imidazo[2,1-c][1,2,4]triazine-3,4-dione | 848892-92-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 8-o-Tolyl-2,6,7,8-tetrahydro-imidazo[2,1-c][1,2,4]triazine-3,4-dione
• 英文别名: 2,6,7,8-Tetrahydro-8-(2-methylphenyl)imidazo[2,1-c][1,2,4]triazine-3,4-dione；8-(2-methylphenyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazine-3,4-dione
• CAS: 848892-92-2
• 化学式: C₁₂H₁₂N₄O₂
• 分子量: 244.253
• InChiKey: FEUFIBGFJGPUKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1-o-tolyl-imidazolidin-2-ylidene)-hydrazine; hydriodide 、 草酸二乙酯 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 8.0h， 以60%的产率得到8-o-Tolyl-2,6,7,8-tetrahydro-imidazo[2,1-c][1,2,4]triazine-3,4-dione
  参考文献：
  名称：

  Identification of antitumour activity of novel derivatives of 8-aryl-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazine-3,4-dione and 8-aryl-4-imino-2,3,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazin-3(6H)-one

  摘要：

  The series of 8-aryl-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazine-3,4-diones (11-20) and 8-aryl-4-imino-2,3,7,8-tetrahydroimidazo[2, I-c][1,2,4]triazin-3(6H)-ones (21-25) were designed and their in vitro cytotoxic activities against human LS180, HeLa, T47D, A549 and RPMI 8226 carcinoma cells are presented. In the crystalline state molecule 12 exists as the predominant tautomeric 3-oxo form. whereas the second possible 3-hydroxy tautomer is not observed. Compound 19 revealed a strong affection to LS180 cancer cells at lower tested concentration (37.9 mu M) and simultaneously was found to be non-toxic towards the normal cell line investigated-GMK cells. Furthermore, this compound was proved to possess the efficiency for DNA strand breakage of the examined cancer cell lines. However, imidazotriazin-3,4-dione 20 was able to cause significant viability decreases in human RPMI 8226 peripheral blood myeloma cells. Compound 22 has exhibited remarkable inhibitory effects against LS180 and A549 carcinoma cells, whereas 24 revealed the highest growth inhibition against A549 cell line. Simultaneously, at lower tested concentration these compounds were proved to be completely non-toxic for GMK cells. Moreover, cytotoxic and antibacterial properties of starting, tautomeric 1-aryl-2-hydrazonoimidazolidines (1-6 and 8-9) are presented. Six of them (1-2, 4-6 and 9) proved active as antimicrobials. All these compounds revealed MIC values in the range of 15.0-78.6 mu M. Their activities were compared to those of ampicillin and chloramphenicol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.024

文献信息

• Antinociceptive activity of new imidazolidine carbonyl derivatives.
  作者：Krzysztof Sztanke、Sylwia Fidecka、Ewa Kędzierska、Zbigniew Karczmarzyk、Kalevi Pihlaja、Dariusz Matosiuk

  DOI：10.1016/j.ejmech.2004.09.020

  日期：2005.2

  Synthesis and pharmacological activity of 8-aryl-3,4-dioxo-2H,8H-6,7-dihydroimidazo[2,1-c] [1,2,4]triazines (A) are presented. The title compounds were obtained from 1-aryl-2-hydrazinoimidazolines (1) by cyclization reaction with ethyl oxalate (2). They were tested for pharmacological activity in behavioral animal tests (A1, A3, A5, A6, A8, A9). With relatively low acute toxicity (LD50 in range from

  介绍了8-芳基-3,4-二氧代-2H，8H-6,7-二氢咪唑并[2,1-c] [1,2,4]三嗪（A）的合成和药理活性。通过与草酸乙酯（2）的环化反应从1-芳基-2-肼基咪唑啉（1）获得标题化合物。在行为动物试验（A1，A3，A5，A6，A8，A9）中对它们的药理活性进行了测试。急性毒性较低（LD50在1100至超过2000 mg kg（-1），腹膜内，ip），其中一些表现出显着的抗伤害感受活性，这表明了“扭体”试验的结果。分别在12.5-200 mg（0.00625-0.1 LD50）和37.5-150 mg（0.025-0.1 LD50）的剂量下观察到对化合物A8特别强的抗伤害感受和对A6显着的抗伤害感受。“扭动”中产生的A1和A8抗伤害感受的还原 用5 mg kg（-1）剂量的纳洛酮进行的试验可表明其镇痛活性类似阿片样物质的机制。另外，化合物A9减少了5-羟色氨酸（5-HTP）给药后
• Identification of antitumour activity of novel derivatives of 8-aryl-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazine-3,4-dione and 8-aryl-4-imino-2,3,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazin-3(6H)-one
  作者：Krzysztof Sztanke、Kazimierz Pasternak、Jolanta Rzymowska、Małgorzata Sztanke、Martyna Kandefer-Szerszeń、Izabela Dybała、Anna E. Kozioł

  DOI：10.1016/j.bmc.2007.02.024

  日期：2007.4

  The series of 8-aryl-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazine-3,4-diones (11-20) and 8-aryl-4-imino-2,3,7,8-tetrahydroimidazo[2, I-c][1,2,4]triazin-3(6H)-ones (21-25) were designed and their in vitro cytotoxic activities against human LS180, HeLa, T47D, A549 and RPMI 8226 carcinoma cells are presented. In the crystalline state molecule 12 exists as the predominant tautomeric 3-oxo form. whereas the second possible 3-hydroxy tautomer is not observed. Compound 19 revealed a strong affection to LS180 cancer cells at lower tested concentration (37.9 mu M) and simultaneously was found to be non-toxic towards the normal cell line investigated-GMK cells. Furthermore, this compound was proved to possess the efficiency for DNA strand breakage of the examined cancer cell lines. However, imidazotriazin-3,4-dione 20 was able to cause significant viability decreases in human RPMI 8226 peripheral blood myeloma cells. Compound 22 has exhibited remarkable inhibitory effects against LS180 and A549 carcinoma cells, whereas 24 revealed the highest growth inhibition against A549 cell line. Simultaneously, at lower tested concentration these compounds were proved to be completely non-toxic for GMK cells. Moreover, cytotoxic and antibacterial properties of starting, tautomeric 1-aryl-2-hydrazonoimidazolidines (1-6 and 8-9) are presented. Six of them (1-2, 4-6 and 9) proved active as antimicrobials. All these compounds revealed MIC values in the range of 15.0-78.6 mu M. Their activities were compared to those of ampicillin and chloramphenicol. (c) 2007 Elsevier Ltd. All rights reserved.