[1-(2-Methoxy-phenyl)-imidazolidin-(2E)-ylidene]-hydrazine | 170746-92-6

• 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: [1-(2-Methoxy-phenyl)-imidazolidin-(2E)-ylidene]-hydrazine
• 英文别名: 2-Hydrazinyl-1-(2-methoxyphenyl)-4,5-dihydro-1H-imidazole；[1-(2-methoxyphenyl)-4,5-dihydroimidazol-2-yl]hydrazine
• CAS: 170746-92-6
• 化学式: C₁₀H₁₄N₄O
• 分子量: 206.247
• InChiKey: IANAHJIDKKQXTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酸二乙酯 、 [1-(2-Methoxy-phenyl)-imidazolidin-(2E)-ylidene]-hydrazine 以 正丁醇 为溶剂， 反应 8.0h， 以60%的产率得到8-(2-methoxyphenyl)-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazine-3,4-dione
  参考文献：
  名称：

  新的咪唑烷羰基衍生物的抗伤害感受活性。第4部分。8-芳基-3,4-二氧代-2H，8H-6,7-二氢咪唑并[2,1-c] [1,2,4]三嗪的合成和药理活性。

  摘要：

  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

  DOI：

  10.1016/j.ejmech.2004.09.020

文献信息

• Novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates from biologically active 1-aryl-2-hydrazinoimidazolines: Synthesis, crystal structure and antiproliferative activity
  作者：Krzysztof Sztanke、Jolanta Rzymowska、Maciej Niemczyk、Izabela Dybała、Anna E. Kozioł

  DOI：10.1016/j.ejmech.2006.06.013

  日期：2006.12

  respectively. Compound 2e revealed antibacterial activity against E. coli ATCC 25922, superior to ampicillin and inferior to chloramphenicol. Against S. aureus ATCC 25923 strain tested, compound 2e demonstrated MIC value inferior to ampicillin and chloramphenicol. Moreover, the synthesis, crystal structure and antiproliferative activity of novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2

  通过与水合肼缩合反应，从合适的1-芳基-2-甲基硫代咪唑啉（1a-h）直接获得1-芳基-2-肼基咪唑啉（2a-h）。介绍了两个1-芳基-2-肼基咪唑啉（2b和2e）的抗​​菌活性。通过IR，（1）H NMR，EI-MS和元素分析证实了它们的化学结构。确定革兰氏阳性和革兰氏阴性细菌菌株，霉菌和酵母样真菌菌株对合成化合物的敏感性以及针对两种参考细菌菌株的MIC值。发现化合物2b相对于参考革兰氏阴性大肠杆菌ATCC 25922细菌菌株具有最强的抗菌活性，最小抑菌浓度（MIC）值为3.91micro g mL（-1）。化合物2b的活性（MIC）优于氨苄西林，与氯霉素相当。发现一种新型化合物2e分别对浓度为7.81micro g mL（-1）和15.62micro g mL（-1）的大肠杆菌ATCC 25922和金黄色葡萄球菌ATCC 25923有效。化合物2e表现出对大肠杆菌ATCC 25922的
• Identification of antibacterial and antiviral activities of novel fused 1,2,4-triazine esters
  作者：Krzysztof Sztanke、Kazimierz Pasternak、Barbara Rajtar、Małgorzata Sztanke、Magdalena Majek、Małgorzata Polz-Dacewicz

  DOI：10.1016/j.bmc.2007.05.048

  日期：2007.8

  The in vitro biological activities of novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates (3a, 3d-j) have been evaluated and are reported. The final heterobicycles (3a-j) were obtained from monocyclic 1-aryl-2-hydrazonoimidazolidines (2a-f) by addition and cyclization reaction with fumaric acid esters. In particular, compounds 3d and 3e were found to exhibit comparable antibacterial potencies in vitro as that of ampicillin. Heterobicycles of the 3e, 3g and 3j type were screened for their antiviral activities against the selected viruses' DNA (human adenovirus type 5-Ad-5) and RNA (human enterovirus-Echo-9). Simultaneously, their cytotoxicities towards HEK-293 and GMK cells were established. In particular, heterobicycle 3j, completely non-toxic for GM K cells, was found to exhibit virucidal properties against Echo-9 virus justifying its further investigation as the potential antiviral agent. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.
• Tkaczynski, Tadeusz; Sztanke, Krzysztof, Acta Poloniae Pharmaceutica, <hi>1995</hi>, vol. 52, # 2, p. 123 - 124
  作者：Tkaczynski, Tadeusz、Sztanke, Krzysztof

  DOI：——

  日期：——
• Sztanke, Krzysztof, Acta Poloniae Pharmaceutica, <hi>2002</hi>, vol. 59, # 3, p. 235 - 236
  作者：Sztanke, Krzysztof

  DOI：——

  日期：——