N-(4-nitrophenyl)-2-phenylhydrazinecarbothioamide | 927407-21-4

• 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: N-(4-nitrophenyl)-2-phenylhydrazinecarbothioamide
• 英文别名: 1-Phenyl-4-(4-nitrophenyl)thiosemicarbazide；1-anilino-3-(4-nitrophenyl)thiourea
• CAS: 927407-21-4
• 化学式: C₁₃H₁₂N₄O₂S
• 分子量: 288.33
• InChiKey: JNCVRLVXCULTFX-UHFFFAOYSA-N

物化性质

• 熔点：
  234-236 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.0±47.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)-2-phenylhydrazinecarbothioamide 、 2,4-二氯苯甲酰氯 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以80%的产率得到5-(2,4-dichlorophenyl)-N-(4-nitrophenyl)-4-phenyl-1,3,4-thiadiazol-4-ium-2-amine;chloride
  参考文献：
  名称：

  通过酰化氨基脲直接环化合成介离子 4-(对位取代苯基-5-2,4-二氯苯基)-1,3-4-噻二唑鎓-2-胺化物

  摘要：

  摘要 十种新型介离子 4-[对位取代 (H, CH3, OCH3, NO2, Cl, Br, OH, t-C4H9, C6H5, C4H9) 苯基-5-2,4-二氯苯基]-1,3 的合成描述了作为盐酸盐的 4-噻二唑鎓-2-胺化物。合成策略利用相应的对位取代异硫氰酸酯作为起始原料，通过与苯肼（61-98%）反应获得氨基硫脲，然后将其与 2,4-二氯苯甲酰氯酰化并直接环化以生成所需的取代基。高产率的介离子化合物（约 80%）。

  DOI：

  10.1080/00397910600941398
• 作为产物：
  描述：

  4-硝基苯胺 以 甲苯 为溶剂， 反应 0.5h， 生成 N-(4-nitrophenyl)-2-phenylhydrazinecarbothioamide
  参考文献：
  名称：

  通过酰化氨基脲直接环化合成介离子 4-(对位取代苯基-5-2,4-二氯苯基)-1,3-4-噻二唑鎓-2-胺化物

  摘要：

  摘要 十种新型介离子 4-[对位取代 (H, CH3, OCH3, NO2, Cl, Br, OH, t-C4H9, C6H5, C4H9) 苯基-5-2,4-二氯苯基]-1,3 的合成描述了作为盐酸盐的 4-噻二唑鎓-2-胺化物。合成策略利用相应的对位取代异硫氰酸酯作为起始原料，通过与苯肼（61-98%）反应获得氨基硫脲，然后将其与 2,4-二氯苯甲酰氯酰化并直接环化以生成所需的取代基。高产率的介离子化合物（约 80%）。

  DOI：

  10.1080/00397910600941398

文献信息

• Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives
  作者：Khalid Mohammed Khan、Saira Qurban、Uzma Salar、Muhammad Taha、Shafqat Hussain、Shahnaz Perveen、Abdul Hameed、Nor Hadiani Ismail、Muhammad Riaz、Abdul Wadood

  DOI：10.1016/j.bioorg.2016.08.010

  日期：2016.10

  Current study based on the synthesis of new thiazole derivatives via "one pot" multicomponent reaction, evaluation of their in vitro α-glucosidase inhibitory activities, and in silico studies. All synthetic compounds were fully characterized by (1)H NMR, (13)C NMR and EIMS. CHN analysis was also performed. These newly synthesized compounds showed activities in the range of IC50=9.06±0.10-82.50±1.70μM

  当前的研究基于通过“一锅”多组分反应合成新的噻唑衍生物，评估其体外α-葡萄糖苷酶抑制活性以及计算机模拟研究。所有合成化合物均通过（1）H NMR，（13）C NMR和EIMS进行了全面表征。还进行了CHN分析。与标准阿卡波糖（IC50 = 38.25±0.12μM）相比，这些新合成的化合物显示的活性在IC50 = 9.06±0.10-82.50±1.70μM范围内。值得一提的是大多数化合物，例如1（IC50 = 23.60±0.39μM），2（IC50 = 22.70±0.60μM），3（IC50 = 22.40±0.32μM），4（IC50 = 26.5±0.40μM） ，6（IC50 = 34.60±0.60μM），7（IC50 = 26.20±0.43μM），8（IC50 = 14.06±0.18μM），9（IC50 = 17.60±0.28μM），10（IC50 = 27.16±0
• UV-visible and ¹H–¹⁵N NMR spectroscopic studies of colorimetric thiosemicarbazide anion sensors
  作者：Kristina N. Farrugia、Damjan Makuc、Agnieszka Podborska、Konrad Szaciłowski、Janez Plavec、David C. Magri

  DOI：10.1039/c4ob02091j

  日期：——

  spectra with all anions, except for chloride, accompanied by dramatic colour changes visible to the naked eye. These changes were determined to be due to the deprotonation of the central N–H proton and not due to hydrogen bonding based on 1H/15N NMR titration studies with acetate in DMSO-d6–0.5% water. Direct evidence for deprotonation was confirmed by the disappearance of the central thiourea proton and

  合成了四个含有三个NH键的硫代半氨基阴离子化学传感器，分别被苯基和/或4-硝基苯基取代，并研究了它们与氢氧根，氟离子，乙酸根，磷酸二氢根和氯离子的阴离子结合能力。阴离子结合特性在DMSO和9：1 DMSO–H 2 O中通过紫外可见吸收和1 H / 13 C / 15 N NMR光谱技术进行了研究，并得到了DFT研究的证实。除氯离子外，所有阴离子在紫外可见吸收光谱中均观察到显着变化，并伴有肉眼可见的显着颜色变化。确定这些变化是由于中央N–H质子的去质子化，而不是由于基于氢的氢键在DMSO- d 6 –0.5％水中用乙酸盐进行的1 H / 15 N NMR滴定研究。中央硫脲质子的消失和乙酸的形成证实了去质子化的直接证据。DFT和电荷分布计算表明，对于所有四种化合物，中心N–H质子的酸性最高。因此，阴离子化学传感器是通过中央N–H质子的去质子化机理而不是通过氢键结合来工作的。
• Novel piperonal 1,3,4-thiadiazolium-2-phenylamines mesoionic derivatives: Synthesis, tyrosinase inhibition evaluation and HSA binding study
  作者：Natália Drumond Lopes、Otávio Augusto Chaves、Márcia C.C. de Oliveira、Carlos Mauricio R. Sant'Anna、Danilo Sousa-Pereira、José Carlos Netto-Ferreira、Aurea Echevarria

  DOI：10.1016/j.ijbiomac.2018.02.050

  日期：2018.6

  A novel series of piperonal mesoionic derivatives (PMI 1–6) was synthesized. Tyrosinase inhibition in the presence of PMI-1, −2, −3, −4, −5 and −6 as well as human serum albumin (HSA) binding studies with PMI-5 and PMI-6 were done by spectroscopic and theoretical methods. The mesoionic compound PMI-5 is the most promising tyrosinase inhibitor with a noncompetitive inhibitory mechanism and an IC50 = 124 μmol L−1

  合成了一系列新的胡椒基中离子衍生物（PMI 1-6）。在PMI-1，-2，-3，-4，-5和-6存在下酪氨酸酶抑制作用以及人血清白蛋白（HSA）与PMI-5和PMI-6的结合研究是通过光谱和理论方法完成的。中离子化合物PMI-5是最有前途的酪氨酸酶抑制剂，具有非竞争性抑制机制，IC 50  = 124μmolL -1。根据动力学曲线，分子对接结果表明PMI-5能够与包含底物分子L-DOPA的酪氨酸酶活性位点良好相互作用，并与Val-247，Phe-263和Val-282残基相互作用。HSA：PMI-5和HSA：PMI-6相互作用的光谱结果表明，这些中离子化合物可以在基态下与HSA缔合，并且能量转移的可能性很高。结合是中等的，自发的，并且可以显着干扰白蛋白的二级结构。分子对接结果表明，PMI-5和PMI-6能够被容纳在HSA的Sudlow位点I内，与疏水和亲水氨基酸残基相互作用。
• Synthesis and biological evaluation of N-aryl-2-phenyl-hydrazinecarbothioamides: Experimental and theoretical analysis on tyrosinase inhibition and interaction with HSA
  作者：Danilo Sousa-Pereira、Otávio Augusto Chaves、Camilla Moretto dos Reis、Márcia C.C. de Oliveira、Carlos Maurício R. Sant'Anna、José Carlos Netto-Ferreira、Aurea Echevarria

  DOI：10.1016/j.bioorg.2018.07.035

  日期：2018.12

  A series of N-aryl-2-phenyl-hydrazinecarbothioamides have been investigated as possible inhibitors of tyrosinase, an enzyme involved in the development of melanomas. The hydrazinecarbothioamides 1-6 were synthesized from the reaction between phenylhydrazine and isothiocyanates, for which three different methods have been employed, namely stirring at room temperature, by microwave irradiation or by mechanochemical grinding. Quantitative yields were obtained for the later technique. Compound 4 showed the best value for tyrosinase inhibition (IC50 = 22.6 mu M), which occurs through an uncompetitive mechanism. Molecular docking results suggested that 4 can interact via T-stacking with the substrate L-DOPA and via hydrogen bonding and hydrophobic forces with the amino acid residues Ala-79, His-243, Val-247, Phe-263, Val-282, and Glu-321. The interaction between human serum albumin (HSA) and compound 4 occurs through a ground state association and does not perturb the secondary structure of the albumin as well as the microenvironment around Tyr and Trp residues. The binding is spontaneous, moderate and occurs mainly in the Sudlow's site I. Molecular docking results suggested hydrogen bonding, hydrophobic and electrostatic interactions as the main binding forces between the compound 4 and the amino acid residues Lys-198, Trp-214, Glu-449, Leu-452, and Leu-480.
• Synthesis of Mesoionic 4‐(<i>para</i>‐substituted Phenyl‐5‐2,4‐dichlorophenyl)‐1,3‐4‐thiadiazolium‐2‐aminides by Direct Cyclization via Acylation of Thiosemicarbazides
  作者：Marcelo Moreira Britto、Tânia Mara Grigolli Almeida、Andrei Leitão、Claudio Luis Donnici、Míriam Tereza Paz Lopes、Carlos Alberto Montanari

  DOI：10.1080/00397910600941398

  日期：2006.11.1

  Abstract The synthesis of ten novel mesoionic 4‐[para‐substituted (H, CH3, OCH3, NO2, Cl, Br, OH, t‐C4H9, C6H5, C4H9) phenyl‐5‐2,4‐dichlorophenyl]‐1,3‐4‐thiadiazolium‐2‐aminides, as hydrochlorides, are described. The synthesis strategy utilized the corresponding para‐substituted isothiocyanates as starting materials to obtain the thiosemicarbazides through reaction with phenylhydrazine (61–98%), which

  摘要 十种新型介离子 4-[对位取代 (H, CH3, OCH3, NO2, Cl, Br, OH, t-C4H9, C6H5, C4H9) 苯基-5-2,4-二氯苯基]-1,3 的合成描述了作为盐酸盐的 4-噻二唑鎓-2-胺化物。合成策略利用相应的对位取代异硫氰酸酯作为起始原料，通过与苯肼（61-98%）反应获得氨基硫脲，然后将其与 2,4-二氯苯甲酰氯酰化并直接环化以生成所需的取代基。高产率的介离子化合物（约 80%）。