4-benzyl-1-(4-nitrobenzoyl)thiosemicarbazide | 282104-46-5

• 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-benzyl-1-(4-nitrobenzoyl)thiosemicarbazide
• 英文别名: N-Benzyl-2-(4-nitrobenzoyl)hydrazinecarbothioamide；1-benzyl-3-[(4-nitrobenzoyl)amino]thiourea
• CAS: 282104-46-5
• 化学式: C₁₅H₁₄N₄O₃S
• mdl: MFCD02062986
• 分子量: 330.367
• InChiKey: OGZZLXGLNMXIIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyl-1-(4-nitrobenzoyl)thiosemicarbazide 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 以63%的产率得到N-benzyl-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  硫代氨基脲中间体的基于试剂的环化反应选择性合成2-氨基取代的1,3,4-恶二唑和1,3,4-噻二唑衍生物

  摘要：

  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。

  DOI：

  10.1021/jo302324r
• 作为产物：
  描述：

  异硫氰酸苯甲酯 、 4-硝基苯酰肼 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-benzyl-1-(4-nitrobenzoyl)thiosemicarbazide
  参考文献：
  名称：

  硫代氨基脲中间体的基于试剂的环化反应选择性合成2-氨基取代的1,3,4-恶二唑和1,3,4-噻二唑衍生物

  摘要：

  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。

  DOI：

  10.1021/jo302324r

文献信息

• 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。
• Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity
  作者：Maciej Wos、Małgorzata Miazga-Karska、Agnieszka A. Kaczor、Katarzyna Klimek、Zbigniew Karczmarzyk、Dorota Kowalczuk、Waldemar Wysocki、Grazyna Ginalska、Zofia Urbanczyk-Lipkowska、Maja Morawiak、Monika Pitucha

  DOI：10.1016/j.biopha.2017.07.049

  日期：2017.9

  A series of thiosemicarbazides with 4-nitrophenyl group was obtained in the reaction of carboxylic acid hydrazides with isothiocyanates. All compounds were checked for their antibacterial and antiproliferative activity. Our results have shown that derivatives possessed antibacterial activity against , , and , moderate cytotoxicity and good therapeutic safety . Additionally, compounds and significantly

  羧酸酰肼与异硫氰酸酯反应得到一系列带有4-硝基苯基的氨基硫脲。检查所有化合物的抗菌和抗增殖活性。我们的结果表明，衍生物具有抗菌活性，具有中等的细胞毒性和良好的治疗安全性。此外，化合物还显着抑制 A549、HepG2 和 MCF-7 细胞分裂。此外，PASS软件表明新获得的化合物是潜在的α-葡萄糖苷酶抑制剂。这已被研究证实。为了研究与分子目标化合物的相互作用模式，将化合物对接至酶的葡萄糖结合位点，并表现出与葡萄糖相似的结合模式。
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• Design and Synthesis of 1,3,4-Thiadiazole Derivatives as Novel Anticancer and Antitubercular Agents
  作者：D. Chandra Sekhar、D. V. Venkata Rao、A. Tejeswara Rao、U. Lav Kumar、Anjali Jha

  DOI：10.1134/s1070363219040224

  日期：2019.4

  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.