1-(p-nitrobenzoyl)-4-phenyl-3-thiosemicarbazide | 17050-22-5

• 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: 1-(p-nitrobenzoyl)-4-phenyl-3-thiosemicarbazide
• 英文别名: N-(p-nitrobenzamido)-N'-phenylthiourea；C6H5NHCSNHNHCOC6H4-p-NO2；1-(4-nitro-benzoyl)-4-phenyl thiosemicarbazide；1-(4-Nitro-benzoyl)-4-phenyl-thiosemicarbazid；2-(4-nitrobenzoyl)-N-phenylhydrazinecarbothioamide；1-[(4-nitrobenzoyl)amino]-3-phenylthiourea
• CAS: 17050-22-5
• 化学式: C₁₄H₁₂N₄O₃S
• 分子量: 316.34
• InChiKey: BHPFDKFQSBZJIL-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 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：
  131
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(p-nitrobenzoyl)-4-phenyl-3-thiosemicarbazide 在 sodium hydroxide 、 碘 、 potassium iodide 作用下， 以 甲醇 为溶剂， 生成 N-phenyl-5-(4-nitrophenyl)-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  质谱研究了2-芳基氨基-5-芳基-1,3,4-恶二唑及其与钴阳离子和环糊精的非共价配合物的断裂和骨架重排。

  摘要：

  通过电子电离（EI）和电喷雾电离（ESI）作为离子产生方法，研究了标题化合物的质谱裂解途径。为了解释观察到的复杂骨架重排，使用了串联质谱，准确的质量测量和同位素标记（恶二唑环中含有一个13 C原子的化合物）。在EI条件下损失CO，N2和H原子导致形成9,10-二氢ac啶型离子，在ESI条件下损失NH3产生4-苯基酞嗪酮型离子，在ESI条件下损失HNCO产生N-芳基氨基苯甲腈离子; 然而，该过程会受到在苯环上取代的基团的电子给体/吸电子性质的影响。ESI用于研究化合物与钴以及环糊精的配合物。

  DOI：

  10.1002/jms.990
• 作为产物：
  描述：

  对硝基苯甲酸乙酯 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 1-(p-nitrobenzoyl)-4-phenyl-3-thiosemicarbazide
  参考文献：
  名称：

  发展ñ -Benzamidothioureas硫脲为基础的受体新一代的阴离子识别和传感

  摘要：

  一系列的中性ñ - （取代的苯甲酰氨基） - ñ ' -phenylthioureas（取代基= p -OC 2 ħ 5，p -CH 3，米-CH 3，H，p -Cl，p -Br，米-Cl，和p -NO 2）被设计为阴离子受体，其中硫脲结合位点通过N-N键与苯甲酰胺基连接。这些N-苯甲酰胺硫脲在乙腈中的吸收光谱在约60nm处达到峰值。270 nm被发现显示出空前的红移了7373至14325 cm - 1在阴离子如ACO的存在-，F - ，和H 2 PO 4 - 。在相同条件下，经典的中性硫脲受体N-（取代的苯基）-N'-苯基硫脲在大多数情况下均表现出小于800 cm - 1的吸收光谱位移，其中6501 cm - 1除外。对照实验，质子溶剂的作用和1 H NMR滴定证实了新的N-苯甲酰胺基硫脲受体和阴离子之间氢键络合物的形成。与ACO的结合常数- ，例如，处于10 5-10 7 mol - 1

  DOI：

  10.1021/jo049088f

文献信息

• Fragmentation and skeletal rearrangements of 2-arylylamino-5-aryl-1,3,4-oxadiazoles and their noncovalent complexes with cobalt cation and cyclodextrin studied by mass spectrometry
  作者：Rafał Frański、Błażej Gierczyk、Grzegorz Schroeder

  DOI：10.1002/jms.990

  日期：2006.3

  studied by electron ionization (EI) and electrospray ionization (ESI) as methods of ion generation. To explain the observed complex skeletal rearrangements, tandem mass spectrometry, accurate mass measurement and isotope labeling (compounds containing one 13C atom in oxadiazole ring) were used. Loss of CO, N2 and H atoms under EI conditions led to the formation of 9,10-dihydroacridine-type ions, loss of

  通过电子电离（EI）和电喷雾电离（ESI）作为离子产生方法，研究了标题化合物的质谱裂解途径。为了解释观察到的复杂骨架重排，使用了串联质谱，准确的质量测量和同位素标记（恶二唑环中含有一个13 C原子的化合物）。在EI条件下损失CO，N2和H原子导致形成9,10-二氢ac啶型离子，在ESI条件下损失NH3产生4-苯基酞嗪酮型离子，在ESI条件下损失HNCO产生N-芳基氨基苯甲腈离子; 然而，该过程会受到在苯环上取代的基团的电子给体/吸电子性质的影响。ESI用于研究化合物与钴以及环糊精的配合物。
• A One-Pot Synthesis of 4,5-Disubstituted-1,2,4-triazole-3-thiones on Solid Support under Microwave Irradiation
  作者：Shahnaz Rostamizadeh、Kambiz Mollahoseini、Samar Moghadasi

  DOI：10.1080/10426500500542992

  日期：2006.8.1

  from the reaction of acid hydrazide 1 with alkyl or aryl isothiocyanate 2 in the presence of a KOH (10%) solution on the surface of silica gel as well as on the surface of montmorillonite K10 under microwave irradiation. These triazoles have also been prepared from the reaction of 4-substituted-1-aroyl thiosemicarbazides 3a–e, with a KOH (10%) solution on the surface of silica gel under microwave irradiation

  4,5-二-取代-1,2,4-三唑-3-硫酮（4a-f）在一个阶段由酰肼 1 与烷基或芳基异硫氰酸酯 2 在 KOH 存在下反应制备（ 10%) 溶液在硅胶表面和蒙脱石 K10 表面在微波照射下。这些三唑也可以通过 4-取代-1-芳酰基氨基硫脲 3a-e 与硅胶表面上的 KOH (10%) 溶液在微波辐射下反应制备。
• Design, synthesis, in vitro and in silico evaluation of novel substituted 1,2,4-triazole analogues as dual human VEGFR-2 and TB-InhA inhibitors
  作者：Amira G. Zawal、Marwa M. Abdel-Aziz、Mahmoud H. Elbatreek、Abdalla A. El-Shanawani、Lobna M. Abdel-Aziz、Samar S. Elbaramawi

  DOI：10.1016/j.bioorg.2023.106883

  日期：2023.12

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• The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating
  作者：Ian R. Baxendale、Steven V. Ley、Marisa Martinelli

  DOI：10.1016/j.tet.2005.03.062

  日期：2005.5

  Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of some 1,3,4-thiadiazole derivatives as inhibitors of Entamoeba histolytica
  作者：Shadab Miyan Siddiqui、Attar Salahuddin、Amir Azam

  DOI：10.1007/s00044-012-0107-x

  日期：2013.3

  In the quest for potent anti-amoebic agents, some 1,3,4-thiadiazole derivatives were synthesized and characterized by spectral data. The purity of the compounds was confirmed by elemental analysis. All the compounds were screened in vitro against HM1:IMSS strain of Entamoeba histolytica by microdilution method. The results revealed that compounds 1 (IC50 = 0.670 mu M), 3 (IC50 = 1.60 mu M) and 8 (IC50 = 0.522 mu M) had much better anti-amoebic activity than the reference drug metronidazole (IC50 = 1.80 mu M). Further, cytotoxicity of the compounds having IC50 value less than metronidazole was assessed by MTT assay on human breast cancer MCF-7 cell line and all the compounds were found low cytotoxic in the concentration range of 2.5-250 mu M. Preliminary results indicate that these three compounds (1, 3 and 8) may be subjected to further investigations and it may be hoped that the present study will stimulate efforts towards the development of novel effective anti-amoebic agents.