4,5-dimethyl-3-(4-methylanilino)-1H-imidazole-2-thione | 1418010-96-4

• 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: 4,5-dimethyl-3-(4-methylanilino)-1H-imidazole-2-thione
• CAS: 1418010-96-4
• 化学式: C₁₂H₁₅N₃S
• 分子量: 233.337
• InChiKey: QHCRYTXYHVCBBH-UHFFFAOYSA-N

物化性质

• 沸点：
  332.9±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4,5,6,7-Tetrahydro-2-benzothiazolyl)-α-chloroacetamid 、 4,5-dimethyl-3-(4-methylanilino)-1H-imidazole-2-thione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以62%的产率得到2-[4,5-dimethyl-1-(p-tolylamino)-1H-imidazol-2-ylthio]-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities

  摘要：

  In this work, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(thiazol-2-yl) acetamide derivatives were synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with some 2-chloro-N-(thiazol-2-yl)acetamide compounds. The structure of synthesized compounds was confirmed by IR, H-1 NMR, and mass spectra. Anticancer activities of the compounds selected by the National Cancer Institute were investigated by testing against a panel of 60 different human tumor cell lines derived from nine neoplastic cancer types. Compounds 7, 13, and 23 exhibited reasonable anticancer activity against the screened cancer types with relatively low GI(50) values. The compounds showed high activity against melanoma-type cell lines.

  DOI：

  10.1007/s00044-012-0411-5
• 作为产物：
  描述：

  sodium thiocyanide 、 3-氯-2-丁酮 、 对甲基苯肼 在 溶剂黄146 作用下， 生成 4,5-dimethyl-3-(4-methylanilino)-1H-imidazole-2-thione
  参考文献：
  名称：

  Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives

  摘要：

  In this work, some new 2-[(4,5-dimethyl-1-(arylamino)-1H-imidazol-2-yl)thio]-1-(aryl) ethanone derivatives were synthesized and investigated for their antibacterial, antifungal and anticancer activities. Toxicity of the most effective compounds was established by performing Brine-Shrimp lethality assay. Antifungal activity of the compounds was found to be higher than antibacterial and anticancer activities of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.024

文献信息

• Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazoles
  作者：Tryfon Zarganes-Tzitzikas、Constantinos G. Neochoritis、Julia Stephanidou-Stephanatou、Constantinos A. Tsoleridis、Gernot Buth、George E. Kostakis

  DOI：10.1016/j.tet.2013.03.096

  日期：2013.6

  5-thione substituent. The thiadiazoles became the only reaction products, formed in very good yield by using 2 equiv of azodicarboxylates. The sodium cyanoborohydride and sodium borohydride reductions to thiadiazoles 11, and 12 were also studied. Plausible mechanistic schemes for the formation of the thiadiazoles are proposed.

  在室温下在偶氮二羧酸盐（1.2当量）存在下，4,5-二取代-N-芳基氨基咪唑-2-硫酮与异氰酸酯反应，形成咪唑并[2,1- b ] [1,3,4]噻二唑唯一的反应产物收率很高，而通过使用更高的反应温度，连同咪唑并[2,1- b ] [1,3,4]噻二唑，也分离出了三组分反应产物，即噻二唑，形成取决于5-硫酮取代基。噻二唑成为唯一的反应产物，通过使用2当量的偶氮二羧酸盐以非常高的收率形成。氰基硼氢化钠和硼氢化钠还原为噻二唑11和12还进行了研究。提出了形成噻二唑的可行机理方案。