1-benzoyl-4-(4-fluorophenyl)-3-thiosemicarbazide | 314766-82-0

• 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-benzoyl-4-(4-fluorophenyl)-3-thiosemicarbazide
• 英文别名: 2-Benzoyl-N-(4-fluorophenyl)hydrazinecarbothioamide；1-benzamido-3-(4-fluorophenyl)thiourea
• CAS: 314766-82-0
• 化学式: C₁₄H₁₂FN₃OS
• 分子量: 289.333
• InChiKey: GQOAAUXYSRCRTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzoyl-4-(4-fluorophenyl)-3-thiosemicarbazide 在 N-甲基吡咯烷酮 、 三乙胺 、 对甲苯磺酰氯 作用下， 以44%的产率得到N-(4-fluorophenyl)-5-phenyl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Design and Synthesis of 1,3,4-Thiadiazole Derivatives as Novel Anticancer and Antitubercular Agents

  摘要：

  A series of novel 5-phenyl-substituted 1,3,4-thiadiazole-2-amines were designed, synthesized, and screened for their antitumor and antitubercular activities. The target compounds were synthesized starting from isocyanates and acid hydrazides by conventional and microwave-assisted protocols. The structures of the products were confirmed by H-1 NMR, C-13 NMR, high-resolution mass spectrometry, and IR spectroscopy and elemental analysis. Some of the synthesized compounds showed significant invitro antitumor activities against breast cancer and normal human cell lines. Among them, N-benzyl-5-(4-fluorophenyl)-, N-benzyl-5-(4-nitrophenyl)-, and 5-phenyl-N-(p-tolyl)-1,3,4-thiadiazole-2-amines demonstrated higher inhibitory activities against the MDA-MB-231 cell line than the cisplatin control (IC50 3.3 M). N-Benzyl-5-(4-methoxyphenyl)-, 5-phenyl-N-[4-(trifluoromethyl)phenyl]methyl-, N-benzyl-5-(4-fluorophenyl)-, and N-benzyl-5-(4-nitrophenyl)-1,3,4-thiadiazole-2-amines exhibited high inhibitory activities against the HEK293T cell line (IC50 52.63, 42.67, 34.71, and 33.74 M, respectively), which were higher compared to the cisplatin control. In antitubercular activity testing against mycobacterium smegmatis MC155, 5-phenyl-N-[4-(trifluoromethyl)-phenyl]methyl-1,3,4-thiadiazole-2-amine proved to be a more potent agent (MIC 26.46 g/mL) compared to the Isoniazid control (12 g/mL). Potential bioactivities of the synthesized compounds were computed using Molinspiration and Molsoft software tools.

  DOI：

  10.1134/s1070363219040224
• 作为产物：
  描述：

  苯甲酸苯酯 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.5h， 生成 1-benzoyl-4-(4-fluorophenyl)-3-thiosemicarbazide
  参考文献：
  名称：

  1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

  摘要：

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

  DOI：

  10.1021/jm0495632

文献信息

• 1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting d-alanine-d-alanine ligase in bacterio
  作者：Alice Ameryckx、Léopold Thabault、Lionel Pochet、Serge Leimanis、Jacques H. Poupaert、Johan Wouters、Bernard Joris、Françoise Van Bambeke、Raphaël Frédérick

  DOI：10.1016/j.ejmech.2018.09.067

  日期：2018.11

  decrease in D-Ala-D-Ala. Further structure-activity relationships (SARs) studies provided evidence that the hydroxyl substituent in the 2-position (R1) of the benzoylthiosemicarbazide scaffold is essential for the enzymatic inhibition. This work thus highlights the 1-(2-hydroxybenzoyl)-thiosemicarbazide motif as a very promising tool for the development of novel antibacterial compounds acting through an

  细菌细胞壁和肽聚糖合成中涉及的酶是开发新型抗菌剂的优先目标。在这项工作中，设计和合成了一系列的D-Ala-D-Ala连接酶（Ddl）的1-（2-羟基苯甲酰基）-硫代氨基脲抑制剂，以针对细菌的耐药菌株为目标。其中，4-（3，4-二氯苯基）-1-（2-羟基苯甲酰基）-3-硫代氨基脲29被认为是有效的Ddl抑制剂，其活性在微摩尔范围内。该化合物具有强大的抗微生物活性，包括针对多药耐药菌株的抗微生物活性，已被证明具有杀菌作用，并且对THP-1人单核细胞系具有极低的细胞毒性。确认抑制Ddl活性达29UPLC-MS / MS证明细菌中D-Ala细胞内池的增加，同时D-Ala-D-Ala也相应减少。进一步的结构活性关系（SARs）研究提供了证据，表明苯甲酰硫基氨基脲骨架的2位（R 1）中的羟基取代基对于酶促抑制是必不可少的。因此，这项工作突出了1-（2-羟基苯甲酰基）-硫代氨基脲基序，它是开发新型抗菌化
• A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
  作者：Binyu Long、Binghua Tian、Qiang Tang、Xiangnan Hu、Lei Han、Zifan Wang、Chenyu Wang、Yue Wu、Yu Yu、Zongjie Gan

  DOI：10.1016/j.tet.2021.132382

  日期：2021.9

  A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room temperature and produced corresponding products in moderate to good yields. This protocol also showed good functional group tolerance.

  通过苯甲酰肼和异硫氰酸酯衍生物的环化脱硫，建立了一种新型、高效且温和的 KHSO 4介导的 2-氨基-1,3,4-恶二唑合成方法。反应在室温下顺利进行，并以中等至良好的收率产生相应的产物。该协议还显示出良好的官能团耐受性。
• Regioselective Synthesis of 2-Amino-Substituted 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate
  作者：Seung-Ju Yang、Seok-Hyeong Lee、Hyun-Jung Kwak、Young-Dae Gong

  DOI：10.1021/jo302324r

  日期：2013.1.18

  is shown in select sets of thiosemicarbazide 3 with R1(benzyl) and R2(phenyl). 2-Amino-1,3,4-oxadiazole 4 was also shown in the reaction of p-TsCl mediated cyclization. The resulting 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole core skeleton are functionalized with various electrophiles such as alkyl halide, acid halides, and sulfornyl chloride in high yields.

  描述了一种基于区域选择性的基于试剂的2-氨基-1,3,4-恶二唑与2-氨基-1,3,4-噻二唑核心骨架环化反应的方法。使硫代氨基脲中间体3与DMSO中的EDC·HCl或p- TsCl，N-甲基-2-吡咯烷酮中的三乙胺反应，得到相应的2-氨基-1,3,4-恶二唑4和2-氨基-1,3 ，4-噻二唑5通过区域选择环化过程。区域选择性是受两个R 1和R 2在p -TsCl介导的环化。在具有R 1（苄基）和R 2的硫代氨基脲3的精选集中显示（苯基）。在对-TsCl介导的环化反应中还显示了2-氨基-1,3,4-恶二唑4。所得的2-氨基-1,3,4-恶二唑和2-氨基-1,3,4-噻二唑核心骨架被各种亲电试剂如烷基卤，酰卤和磺酰氯高官能度地官能化。
• Antimicrobial and Physicochemical Characterizations of Thiosemicarbazide and <i>S</i>-Triazole Derivatives
  作者：Edyta Kuśmierz、Agata Siwek、Urszula Kosikowska、Anna Malm、Tomasz Plech、Andrzej Wróbel、Monika Wujec

  DOI：10.1080/10426507.2014.902831

  日期：2014.10.3

  GRAPHICAL ABSTRACT Abstract Two series of thiosemicarbazide derivatives and three series of s-triazole derivatives have been synthesized. All of these compounds were tested for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. Among tested thiosemicarbazide derivatives, the best bioactivity was detected for two 1-formylthiosemicarbazides with 3-/4-tolyl

  图形摘要摘要已合成了两个系列氨基硫脲衍生物和三个系列的s-三唑衍生物。测试了所有这些化合物对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。在测试的氨基硫脲衍生物中，检测到两种具有 3-/4-甲苯基取代（1 l，1 m）的 1-甲酰氨基硫脲的最佳生物活性（MIC 范围在 31.25 和 250 μg/mL 之间）。所有测试的 s-三唑衍生物的抗菌活性都低于它们的无环前体。
• 1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation
  作者：Elçin E. Oruç、Sevim Rollas、Fatma Kandemirli、Nathaly Shvets、Anatholy S. Dimoglo

  DOI：10.1021/jm0495632

  日期：2004.12.1

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.