1-(2-phenylethyl)-3-[3-(trifluoromethyl)phenyl]thiourea

• 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-phenylethyl)-3-[3-(trifluoromethyl)phenyl]thiourea
• 英文别名: 1-phenylethyl-3-(3-(trifluoromethyl)phenyl)thiourea；1-Phenethyl-3-[3-(trifluoromethyl)phenyl]thiourea
• 化学式: C₁₆H₁₅F₃N₂S
• 分子量: 324.37
• InChiKey: JRMUKNKNVDZSFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethyl)-3-[3-(trifluoromethyl)phenyl]thiourea 、 水 、 copper dichloride 以 N,N-二甲基甲酰胺 为溶剂， 以54 %的产率得到
  参考文献：
  名称：

  新型 Cu(II) 配合物与 3-(三氟甲基) 苯基硫脲衍生物的合成、结构表征和生物活性评价。

  摘要：

  合成了铜配合物与 1,3-二取代硫脲衍生物，均含有 3-(三氟甲基) 苯基尾和 1-烷基/卤素-苯基取代基。实验光谱研究和理论计算表明，两个配体通过硫代羰基 S 和硫脲部分的去质子化 N 原子以双齿方式与 Cu(II) 配位。此类单体是烷基苯基硫脲络合物的特征，而卤代衍生物则观察到三明治型二聚体的形成。首次展示了使用实验和理论 X 射线吸收近边结构对基于 CuN2S2 的配合物进行结构鉴定。与烷基苯基硫脲复合物相比，二聚卤代衍生物显示出更高的抗菌活性。1-(4-氯-3-硝基苯基)-3-[3-(三氟甲基)苯基]硫脲的 Cu(II) 复合物对 19 株耐甲氧西林葡萄球菌 (MIC = 2 µg/mL) 具有活性。该衍生物作为从金黄色葡萄球菌中分离出的 DNA 促旋酶和拓扑异构酶 IV 的双重抑制剂。此外，卤代苯基硫脲复合物强烈抑制从结核病患者身上分离出的分枝杆菌的生长，甚至比参考异烟肼强四倍。复合物发挥弱至中等抗肿瘤活性（针对

  DOI：

  10.3390/ijms232415694
• 作为产物：
  描述：

  间氨基三氟甲苯 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 1-(2-phenylethyl)-3-[3-(trifluoromethyl)phenyl]thiourea
  参考文献：
  名称：

  Design, synthesis, biological activities, and dynamic simulation study of novel thiourea derivatives with gibberellin activity towards Arabidopsis thaliana

  摘要：

  Computer-aided drug design has advanced by leaps and bounds, and has been widely used in various fields, and especially in the field of drug discovery. Although the crystal structure of the gibberellin (GA) receptor GID1A had been reported in previous studies, there is still a lack of designs of gibberellin functional analogue based GID1A. In the present study, a series of 30 thiourea derivatives were designed, synthesized and biologically assayed. The results suggested that the synthetic compounds had good GA-like activities. Furthermore, the structure-activity relationship of the synthetic compounds was discussed, and the dynamic simulation and docking study revealed the binding properties of the GID1A receptor and compounds Y1, Y11, and Y21.

  DOI：

  10.1016/j.bmc.2019.06.032

文献信息

• Synthesis, cytotoxicity and antimicrobial activity of thiourea derivatives incorporating 3-(trifluoromethyl)phenyl moiety
  作者：Anna Bielenica、Joanna Stefańska、Karolina Stępień、Agnieszka Napiórkowska、Ewa Augustynowicz-Kopeć、Giuseppina Sanna、Silvia Madeddu、Stefano Boi、Gabriele Giliberti、Małgorzata Wrzosek、Marta Struga

  DOI：10.1016/j.ejmech.2015.06.027

  日期：2015.8

  A total of 31 of thiourea derivatives was prepared reacting 3-(trifluoromethyl)aniline and commercial aliphatic and aromatic isothiocyanates. The yields varied from 35% to 82%. All compounds were evaluated in vitro for antimicrobial activity. Derivatives 3, 5, 6, 9, 15, 24 and 27 showed the highest inhibition against Gram-positive cocci (standard and hospital strains). The observed MIC values were

  制备了总共31种使3-（三氟甲基）苯胺与市售脂族和芳族异硫氰酸酯反应的硫脲衍生物。产率从35％到82％不等。在体外评估所有化合物的抗微生物活性。衍生物3，5，6，9，15，24和27显示出对革兰氏阳性球菌（标准和医院的菌株）的最高抑制。观察到的MIC值在0.25–16μg/ ml的范围内。研究了硫脲5和15对从金黄色葡萄球菌分离的拓扑异构酶IV的抑制活性。产品5和15有效抑制了耐甲氧西林和表皮葡萄球菌的标准菌株的生物膜形成。此外，评估了所有获得的硫脲对大量DNA和RNA病毒的细胞毒性和抗病毒活性。化合物5,6，8-12，15导致细胞毒性对MT-4细胞（CC 50  ≤10μM）。
• 5-HT 2 receptor affinity, docking studies and pharmacological evaluation of a series of 1,3-disubstituted thiourea derivatives
  作者：Anna Bielenica、Ewa Kędzierska、Michał Koliński、Sebastian Kmiecik、Andrzej Koliński、Ferdinando Fiorino、Beatrice Severino、Elisa Magli、Angela Corvino、Ilaria Rossi、Paola Massarelli、Anna E. Kozioł、Aleksandra Sawczenko、Marta Struga

  DOI：10.1016/j.ejmech.2016.03.073

  日期：2016.6

  A series of 10 thiourea derivatives have been synthesized by the reaction of aromatic amine with a substituted aryl (compounds 1–3, 6–8) and alkylphenyl (4, 5, 9, 10) isothiocyanates. Their in vitro and in vivo pharmacological properties were studied. Among the evaluated compounds, two displayed very high affinity for the 5-HT2A receptor (1–0.043 nM and 5–0.6 nM), being selective over the 5-HT2C receptor

  一系列10个硫脲衍生物的已被芳族胺与取代的芳基反应，合成（化合物1-3，6-8）和烷基苯（4，5，9，10）异硫氰酸酯。研究了它们的体外和体内药理特性。中所评估的化合物中，两个显示非常高的亲和性对5-HT 2A受体（1 -0.043纳米和5 -0.6 nm）时，具有选择性在5-HT 2C受体。衍生物3，5，9，10减少了70–89％，降低了L-5-HTP引起的头部抽搐发作。作为5-HT 2A受体拮抗剂的化合物1和5在DOI诱导的HTR数量上呈剂量依赖性降低。化合物1-5可以大大降低啮齿类动物中苯丙胺引起的过度活跃。在另一项测试中，1和2引起小鼠体温过高，而9和10导致体温过低。证明了所选衍生物的镇痛和抗惊厥特性。使用5-HT 2A同源模型进行分子对接研究 揭示了硫脲NH基团和Asp155 / Tyr370残基之间氢键的重要作用，以及与Phe339的π-π相互作用。
• Design, synthesis, biological activities, and dynamic simulation study of novel thiourea derivatives with gibberellin activity towards Arabidopsis thaliana
  作者：Zhikun Yang、Jine Wang、Hao Tian、Yan He、Hongxia Duan、Liusheng Duan、Weiming Tan

  DOI：10.1016/j.bmc.2019.06.032

  日期：2019.10

  Computer-aided drug design has advanced by leaps and bounds, and has been widely used in various fields, and especially in the field of drug discovery. Although the crystal structure of the gibberellin (GA) receptor GID1A had been reported in previous studies, there is still a lack of designs of gibberellin functional analogue based GID1A. In the present study, a series of 30 thiourea derivatives were designed, synthesized and biologically assayed. The results suggested that the synthetic compounds had good GA-like activities. Furthermore, the structure-activity relationship of the synthetic compounds was discussed, and the dynamic simulation and docking study revealed the binding properties of the GID1A receptor and compounds Y1, Y11, and Y21.
• Synthesis, Structural Characterization and Biological Activity Evaluation of Novel Cu(II) Complexes with 3-(trifluoromethyl)phenylthiourea Derivatives
  作者：Aleksandra Drzewiecka-Antonik、Marta Struga、Agnieszka Głogowska、Ewa Augustynowicz-Kopec、Katarzyna Dobrzyńska、Alicja Chrzanowska、Anna Wolska、Paweł Rejmak、Marcin T. Klepka、Małgorzata Wrzosek、Anna Bielenica

  DOI：10.3390/ijms232415694

  日期：——

  complexes, whereas the formation of a sandwich-type dimer is observed for halogeno derivatives. For the first time, the structural identifications of CuN2S2-based complexes using experimental and theoretical X-ray absorption near edge structure are demonstrated. The dimeric halogeno derivatives showed higher antimicrobial activity in comparison with alkylphenylthiourea complexes. The Cu(II) complex of 1-(

  合成了铜配合物与 1,3-二取代硫脲衍生物，均含有 3-(三氟甲基) 苯基尾和 1-烷基/卤素-苯基取代基。实验光谱研究和理论计算表明，两个配体通过硫代羰基 S 和硫脲部分的去质子化 N 原子以双齿方式与 Cu(II) 配位。此类单体是烷基苯基硫脲络合物的特征，而卤代衍生物则观察到三明治型二聚体的形成。首次展示了使用实验和理论 X 射线吸收近边结构对基于 CuN2S2 的配合物进行结构鉴定。与烷基苯基硫脲复合物相比，二聚卤代衍生物显示出更高的抗菌活性。1-(4-氯-3-硝基苯基)-3-[3-(三氟甲基)苯基]硫脲的 Cu(II) 复合物对 19 株耐甲氧西林葡萄球菌 (MIC = 2 µg/mL) 具有活性。该衍生物作为从金黄色葡萄球菌中分离出的 DNA 促旋酶和拓扑异构酶 IV 的双重抑制剂。此外，卤代苯基硫脲复合物强烈抑制从结核病患者身上分离出的分枝杆菌的生长，甚至比参考异烟肼强四倍。复合物发挥弱至中等抗肿瘤活性（针对