methyl 2-(4-oxo-8-phenyl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl 2-(4-oxo-8-phenyl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetate
• 英文别名: Methyl 2-(4-oxo-8-phenyl-2,3,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetate
• 化学式: C₁₄H₁₆N₄O₃
• 分子量: 288.306
• InChiKey: MJWZADWNNHQZFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Hydroiodid v. 1-Phenyl-2-methylthio-Δ²-imidazolin 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 36.0h， 生成 methyl 2-(4-oxo-8-phenyl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetate
  参考文献：
  名称：

  甲基和乙基2-（4-oxo-8-芳基-2H-3,4,6,7-四氢咪唑并[2,1-c] [1,2,4]三嗪-3-基）乙酸酯的衍生物具有生物活性的1-芳基-2-肼基咪唑啉：合成，晶体结构和抗增殖活性。

  摘要：

  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

  DOI：

  10.1016/j.ejmech.2006.06.013

文献信息

• 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.
• 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