1-[(4-chlorophenyl)amino]-1,3-dihydro-4,5-dimethyl-2H-imidazole-2-thione | 1022903-95-2

• 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-[(4-chlorophenyl)amino]-1,3-dihydro-4,5-dimethyl-2H-imidazole-2-thione
• 英文别名: 3-(4-chloroanilino)-4,5-dimethyl-1H-imidazole-2-thione
• CAS: 1022903-95-2
• 化学式: C₁₁H₁₂ClN₃S
• 分子量: 253.755
• InChiKey: APHCAKYWPVYIFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  异氰环已烷 、 1-[(4-chlorophenyl)amino]-1,3-dihydro-4,5-dimethyl-2H-imidazole-2-thione 在 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以84%的产率得到3-(4-chlorophenyl)-2-cyclohexylimino-2,3-dihydro-5,6-dimethyl-imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  偶氮二羧酸盐：用于新型1,3,4-噻二唑和咪唑并[2,1- b ] [1,3,4]噻二唑的多组分合成的有价值的试剂

  摘要：

  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。

  DOI：

  10.1016/j.tet.2013.03.096
• 作为产物：
  描述：

  sodium thiocyanide 、 3-氯-2-丁酮 、 4-氯苯肼 在 溶剂黄146 作用下， 生成 1-[(4-chlorophenyl)amino]-1,3-dihydro-4,5-dimethyl-2H-imidazole-2-thione
  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

文献信息

• First catalytic hetero-Diels–Alder reaction of imidazole-2-thiones and in silico biological evaluation of the cycloadducts
  作者：Nikolaos Eleftheriadis、Evanthia Samatidou、Constantinos G. Neochoritis

  DOI：10.1016/j.tet.2016.02.034

  日期：2016.4

  reactions of suitably substituted imidazole-2-thiones with dienes were studied. It was found that the electron density of the imidazole core influenced the reaction, since electron withdrawing groups led to the novel spiro-derivatives 2 whereas electron donating groups gave rise to the sulfur substituted imidazole derivatives 6. The reaction conditions were optimized and full assignment of all 1H and 13C

  研究了路易斯酸催化适当取代的咪唑-2-硫酮与二烯的狄尔斯-阿尔德反应。发现咪唑核心的电子密度影响了反应，因为吸电子基团导致了新型螺衍生物2，而供电子基团产生了硫取代的咪唑衍生物6。优化了反应条件，并明确实现了所有1 H和13 C NMR化学位移的完全分配。在计算机上通过三种不同蛋白质的分子建模对环加合物进行了计算机评估，并计算了ADME-Tox特性。
• 1-Arylaminoimidazole-2-thiones as intermediates in the synthesis of imidazo[2,1-b][1,3,4]thiadiazines
  作者：Constantinos Neochoritis、Constantinos A. Tsoleridis、Julia Stephanidou-Stephanatou

  DOI：10.1016/j.tet.2008.01.136

  日期：2008.4

  The synthesis of the hitherto unknown imidazo[2,1-b][1,3,4]thiadiazines 7 in good to very good yields (up to 77%) by using suitable imidazole-2-thione precursors 1 has been described, while S-vinylimidazoles 8 and 9 were isolated as by-products. Moreover, the reactivity of the three possible reaction sites of the starting thiones 1 was initially examined by methylation experiments, whereupon the enhanced

  已经描述了通过使用合适的咪唑-2-硫酮前体1合成迄今未知的咪唑并[2,1- b ] [1,3,4]噻二嗪7的收率非常好（高达77％）。分离出S-乙烯基咪唑8和9作为副产物。此外，最初通过甲基化实验检查了起始硫酮1的三个可能反应位点的反应性，随后通过分离甲基化衍生物3和4证明了硫的反应性增强。通过长时间的甲基化，咪唑啉酮6终于形成了。理论计算支持了烷基化产物的实验结果。
• A thorough study on the reaction of DMAD with 1-arylaminoimidazole-2-thiones. Expeditious synthesis of imidazo[2,1-b][1,3]thiazoles through a novel arylamino rearrangement
  作者：Constantinos Neochoritis、Nicolaos Eleftheriadis、Constantinos A. Tsoleridis、Julia Stephanidou-Stephanatou

  DOI：10.1016/j.tet.2009.11.056

  日期：2010.1

  Upon reaction of 1-arylamino-imidazole-2-thiones 1 with dimethyl acetylenedicarboxylate (DMAD) in the presence of 2.2 equiv of sodium hydride, imidazothiazoles 4 were exclusively formed (71–82% yield). However, from the reaction of 1 with DMAD in the absence of base, only the S-substituted products 5 were formed as an E/Z mixture (53–55%), which could also be converted to 4 with 2.0 equiv of sodium

  在存在2.2当量的氢化钠的情况下，使1-芳基氨基-咪唑-2-硫酮1与乙酰二羧酸二甲酯（DMAD）反应后，仅形成咪唑并噻唑4（产率为71–82％）。但是，从1与DMAD在不存在碱的情况下反应，仅形成S取代的产物5为E / Z混合物（53-55％），也可以用2.0当量的氢化钠将其转化为4（65–68％）。此外，将5a - E / Z转化为芳基氨基取代的衍生物8a与1.1当量的氢化钠反应后，产率为78％。在甲醇中存在甲醇钠的情况下，硫酮1a与DMAD的反应也可能形成8a（75％的收率）。通过用DMAD（91％）加热1a或加热苯中的5a - E / Z混合物（90％收率）观察到硫酮1a的咪唑3-NH取代生成6a - Z。最后，当5a - E与乙酸酐反应时，乙酰化衍生物7a - Z是唯一的分离产物（58％）。全部分配明确实现了1 H和13 C NMR化学位移。
• Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives
  作者：Leyla Yurttaş、Murat Duran、Şeref Demirayak、Hülya Karaca Gençer、Yağmur Tunalı

  DOI：10.1016/j.bmcl.2013.10.024

  日期：2013.12

  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.