N-phenyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide | 64612-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-phenyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide
• 英文别名: 4-(phenyl)-1-(thiophene-2-carbonyl)thiosemicarbazide；N-phenyl-2-(thiophene-2-carbonyl)hydrazine-1-carbothioamide；N-phenyl-2-(2-thienylcarbonyl)hydrazinecarbothioamide；1-phenyl-3-(thiophene-2-carbonylamino)thiourea
• CAS: 64612-84-6
• 化学式: C₁₂H₁₁N₃OS₂
• mdl: MFCD00245615
• 分子量: 277.371
• InChiKey: HNOZXLPXQCPGFX-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C(Solv: ethanol (64-17-5))
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  114
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide 在 乙醇 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-[(4-methylpiperidin-1-yl)methyl]-4-phenyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

  摘要：

  A novel series of compounds were synthesized by cyclic condensation reaction of substituted isothiocyanate (2a-c) with 2-thiophenecarboxylic acid hydrazide (1) in the presence of ethyl alcohol, to obtain intermediate thiosemicarbazides (3a-c), which were further treated with sodium hydroxide in the presence of ethanol to obtain triazole derivatives (4a-c). The latter were refluxed with substituted secondary amines and formaldehyde for 6-10 h to afford Mannich bases (5a-k). The synthesized compounds were characterized on the basis of their spectral (IR, C-13 and H-1 NMR) data and evaluated for biological activities. Some of the compounds were found to exhibit significant antimicrobial and antioxidant activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.025
• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 hydrazine hydrate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.25h， 生成 N-phenyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Design, synthesis and characterization of some novel 4-aminoantipyrine derivatives and evaluation of their activity as analgesic agents

  摘要：

  DOI：

  10.32383/appdr/144130

文献信息

• 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。
• 1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation
  作者：Katarzyna Dzitko、Agata Paneth、Tomasz Plech、Jakub Pawełczyk、Paweł Stączek、Joanna Stefańska、Piotr Paneth

  DOI：10.3390/molecules19079926

  日期：——

  A series of 4-arylthiosemicarbazides substituted at the N1 position with a 5-membered heteroaryl ring was synthesized and evaluated in vitro for T. gondii inhibition proliferation and host cell cytotoxicity. At non-toxic concentrations for the host cells all studied compounds displayed excellent anti-parasitic effects when compared to sulfadiazine, indicating a high selectivity of their anti-T. gondii activity. The differences in bioactivity investigated by DFT calculations suggest that the inhibitory activity of 4-aryl-thiosemicarbazides towards T. gondii proliferation is connected with the electronic structure of the molecule. Further, these compounds were tested as potential antibacterial agents. No growth-inhibiting effect on any of the test microorganisms was observed for all the compounds, even at high concentrations.

  研究人员合成了一系列 N1 位被 5 元杂芳基环取代的 4-芳基硫代氨基甲酸盐，并在体外评估了它们对淋球菌增殖的抑制作用和对宿主细胞的细胞毒性。在对宿主细胞无毒的浓度下，与磺胺嘧啶相比，所有研究化合物都显示出了极佳的抗寄生虫效果，这表明它们的抗淋球菌活性具有很高的选择性。通过 DFT 计算研究的生物活性差异表明，4-芳基-硫代氨基甲酸盐对淋球菌增殖的抑制活性与分子的电子结构有关。此外，这些化合物还被测试为潜在的抗菌剂。即使在高浓度下，也没有观察到所有化合物对任何受试微生物有抑制生长的作用。
• A new and efficient synthesis of 1,3,4-oxadiazole derivatives using TBTU
  作者：Shokoofeh Maghari、Sorour Ramezanpour、Fatemeh Darvish、Saeed Balalaie、Frank Rominger、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tet.2012.11.071

  日期：2013.2

  An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from isothiocyanates and hydrazides through cyclodesulfurization in the presence of (O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate) TBTU as an uronium coupling reagent has been developed. The present methodology offers several advantages, such as simple and easy work-up procedures, mild reaction conditions

  用于从异硫氰酸酯和酰肼2,5-二取代的1,3,4-恶二唑，通过环化脱硫中的（存在下合成的有效方法Ô（苯并三唑-1-基） - - ñ，Ñ，N' ，N' -已经开发出四甲基脲鎓四氟硼酸酯（TBTU）作为铀偶联剂。本方法具有几个优点，例如简单和容易的后处理程序，温和的反应条件，并且对环境无害。
• Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1,3,4-oxadiazoles from 1-acylthiosemicarbazides
  作者：Jaime Crispim-Neto、Marcio C.S. de Mattos

  DOI：10.1016/j.tetlet.2023.154494

  日期：2023.5

  conversion of 1-acylthiosemicarbazides into 2-amino-1,3,4-oxadiazoles by the reaction with tribromoisocyanuric acid. 1-Acylthiosemicarbazides with diverse substituents such as alkyl, benzyl, and (hetero)aryl were prepared from acylhydrazides and isothiocyanates in up to 97% yield and converted into respective 2-amino-1,3,4-oxadiazoles in 19–93% yield This protocol presents simple reaction conditions,

  已开发出一种简单、有效且环境友好的方法，通过与三溴异氰尿酸反应将 1-酰基氨基硫脲转化为 2-氨基-1,3,4-恶二唑。由酰肼和异硫氰酸酯制备具有不同取代基（如烷基、苄基和（杂）芳基）的 1-酰基氨基硫脲，收率高达 97%，并以 19–93% 的收率转化为相应的 2-氨基-1,3,4-恶二唑该协议提供了简单的反应条件、易于获取的试剂，无需任何特殊设备。
• Synthesis, computational chemical study, antiproliferative activity screening, and molecular docking of some thiophene-based oxadiazole, triazole, and thiazolidinone derivatives
  作者：Amna S. Elgubbi、Eman A. E. El-Helw、Abdullah Y. A. Alzahrani、Sayed K. Ramadan

  DOI：10.1039/d3ra07048d

  日期：——

  (CA IX) protein. The binding energies of these ligands were near to that of the co-crystallized ligand (9FK). Compound 11b exhibits a binding energy of −5.5817 kcal mol−1, indicating tight binding to some key nucleobases and amino acids of CA IX protein, while compound 11a displays a higher binding energy compared to the reference ligand (9FK). This suggests that compounds 11b and 11a display a notably

  本研究中使用噻吩-2-碳酰肼通过与各种碳中心亲电子试剂反应生成一些含噻吩的恶二唑、三唑和噻唑烷酮衍生物。此外，所得腙与巯基乙酸和乙酸酐反应，构建噻唑烷酮和恶二唑衍生物。计算化学研究的结果和实验结果非常吻合。使用阿霉素作为参考抗癌剂，检查了所产生的化合物针对两种人类细胞系，即乳腺癌（MCF7）和结肠癌（HCT116）细胞系的体外抗增殖活性。产生的腙和螺二氢吲哚恶二唑衍生物对两种癌细胞系最有效。进行分子对接是为了证明所产生的物质与人碳酸酐酶 IX (CA IX) 蛋白的结合能。这些配体的结合能接近共结晶配体（9FK）的结合能。化合物11b表现出-5.5817 kcal mol -1的结合能，表明与CA IX蛋白的一些关键核碱基和氨基酸紧密结合，而化合物11a与参考配体(9FK)相比表现出更高的结合能。这表明化合物11b和11a对人碳酸酐酶 IX (CA IX) 蛋白表现出显着强的结合亲和力。预测了有效化合物的