1,3-dihydro-4,5-dimethyl-1-(phenylamino)-2H-imidazole-2-thione | 191349-02-7

• 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: 1,3-dihydro-4,5-dimethyl-1-(phenylamino)-2H-imidazole-2-thione
• 英文别名: 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione；3-anilino-4,5-dimethyl-1H-imidazole-2-thione
• CAS: 191349-02-7
• 化学式: C₁₁H₁₃N₃S
• 分子量: 219.31
• InChiKey: UMJYDQRWRNVIGW-UHFFFAOYSA-N

物化性质

• 熔点：
  229-231 °C
• 沸点：
  316.8±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：

  1,3-dihydro-4,5-dimethyl-1-(phenylamino)-2H-imidazole-2-thione 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以75%的产率得到4,5-dimethyl-1-phenylamino-1H-imidazole
  参考文献：
  名称：

  1-Arylamino-1H-imidazoles by "Oxidative Reduction" --- Conversion of 1-Arylamino-2,3-dihydro-1H-imidazole-2-thiones

  摘要：

  DOI：

  10.3987/com-98-8116
• 作为产物：
  描述：

  sodium thiocyanide 、 3-氯-2-丁酮 、 苯肼 在 溶剂黄146 作用下， 生成 1,3-dihydro-4,5-dimethyl-1-(phenylamino)-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

• 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。
• 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。
• Hiv inhibiting n-aminoimidazole derivatives
  申请人：——

  公开号：US20040122024A1

  公开（公告）日：2004-06-24

  An N-aminoimidazole or N-aminoimidazolethione derivative, a pharmaceutically acceptable salt, a tautomer, an isomer, an ester or glycosylation product thereof, said derivative being represented by general formula (I): wherein m=zero or 1, n=zero or 1, R 1 is selected from hydrogen, methyl or ethyl, R 2 is selected from hydrogen, SH or —SR 0 wherein R 0 is methyl, benzyl or glucose residue; Q is selected from 1-naphtyl, 2-naphtyl, biphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, thienyl, or a substituted or unsubstituted phenyl ring, wherein the substitution is understood as being one or two substituents selected from H, F, Cl, Br, I, methyl, ethyl or isopropyl; L is selected from 1-naphtyl, 2-naphtyl, biphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, thienyl, or a substituted or unsubstituted phenyl ring wherein the substitution is understood as being one or two substituents selected from H, F, Cl, Br, I, methyl, ethyl or isopropyl. This invention further relates to the use of compounds of formula (I) as agents having biological activity, especially against viral infections.

  一种N-氨基咪唑或N-氨基咪唑硫醇衍生物，其药学上可接受的盐，互变异构体，异构体，酯或糖基化产物，所述衍生物由通式（I）表示： 其中m=0或1，n=0或1，R1选自氢，甲基或乙基，R2选自氢，SH或-SR0，其中R0为甲基，苄基或葡萄糖残基；Q选自1-萘基，2-萘基，联苯，2-吡啶基，3-吡啶基，4-吡啶基，2-嘧啶基，4-嘧啶基，5-嘧啶基，噻吩基或取代或未取代的苯环，其中取代被理解为是选择H，F，Cl，Br，I，甲基，乙基或异丙基中的一个或两个取代基；L选自1-萘基，2-萘基，联苯，2-吡啶基，3-吡啶基，4-吡啶基，2-嘧啶基，4-嘧啶基，5-嘧啶基，噻吩基或取代或未取代的苯环，其中取代被理解为是选择H，F，Cl，Br，I，甲基，乙基或异丙基中的一个或两个取代基。本发明还涉及将式（I）化合物作为具有生物活性的药物，特别是用于抗病毒感染。