N-phenyl-2-tosylhydrazinecarbothioamide | 28744-12-9

• 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-phenyl-2-tosylhydrazinecarbothioamide
• 英文别名: 4-phenyl-1-(toluene-4-sulfonyl)-thiosemicarbazide；4-Phenyl-1-(toluol-4-sulfonyl)-thiosemicarbazid；1-p-Toluenesulfonyl-4-phenyl-3-thiosemicarbazide；1-p-Toluolsulfonyl-4-phenyl-thiosemicarbazid；p-Toluolsulfonyl-4-phenyl-3-thiosemicarbazid；2-[(4-methylphenyl)sulfonyl]-N-phenylhydrazinecarbothioamide；1-[(4-methylphenyl)sulfonylamino]-3-phenylthiourea
• CAS: 28744-12-9
• 化学式: C₁₄H₁₅N₃O₂S₂
• 分子量: 321.424
• InChiKey: YCZRVDXTUMRYJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C (decomp)
• 沸点：
  469.6±38.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯化三(三苯基膦)铜(I) 、 N-phenyl-2-tosylhydrazinecarbothioamide 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到chlorido(N-phenyl-2-tosylhydrazinecarbothioamide)bis-triphenylphosphane copper(I)
  参考文献：
  名称：

  Cu(I) complexes with thiosemicarbazides derived from p-toluenesulfohydrazide: Structural, luminescence and biological studies

  摘要：

  Reactions of thiosemicarbazide ligands (L-R: R = cyclohexyl (Cy) or phenyl (Ph)) with [CuCl(PPh3)(3)] led to the formation of colorless Cu(I) complexes of composition [CuCl(PPh3)(2)(L-R)]. Both complexes were characterized by spectroscopic methods and further studied by single crystal X-ray diffractometry. The crystal structures confirmed the tetrahedral geometry for the Cu(I) metal center, which is coordinated by a chlorido, two triphenylphosphane and by the thiosemicarbazide as a neutral S-donor monodentate ligand. Photophysical studies revealed that the complexes exhibit emission at room temperature with maxima around 480 nm. At 77 K, the emission is shifted to higher energy, a characteristic behavior of MLCT emitters. The main low lying molecular orbitals were calculated by TD-DFT and confirmed that the S-0 -> S-1 transitions have mainly MLCT character as well as that the peripheral groups in the thiosemicarbazide ligand play an important role on this transition. Moreover, the emission bands are considerably suppressed in the presence of O-2, indicating the triplet character of the emitter excited states. The intersystem crossing process is also suggested by the energy diagrams built through TD-DFT calculations. Overall, both experimental and theoretical analysis suggest (MLCT)-M-3 radiative decays occurrence for the complexes. Furthermore, biological assays showed that the complexes are active on the intracellular amastigote form of Trypanosoma cruzi (Tulahuen Lac-Z strain), and present a significant cytotoxic effect against metastatic melanoma cells. Finally, no significant toxicity to LLC-MK2 cells was observed, resulting in a therapeutic index of about 30 for one of the complexes, in the same order of magnitude as that of the standard drug benznidazole. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.08.013
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 对甲苯磺酰肼 以 四氢呋喃 为溶剂， 以80%的产率得到N-phenyl-2-tosylhydrazinecarbothioamide
  参考文献：
  名称：

  3-芳基磺酰基-5-芳基氨基-1,3,4-噻二唑-2（3H）ones作为抗炎和止痛药。

  摘要：

  制备并测试了具有潜在抗炎和镇痛活性的两个系列的3-芳基磺酰基-5-芳基氨基-1,3,4-噻二唑-2（3H）ones 2。药理结果表明，所有标题化合物均具有芳基磺酰基侧链，具有良好的止痛活性和良好的抗炎特性。通过乙酸扭体试验评估的这两个系列的镇痛曲线表明，化合物2c，2f和2h特别是活性最高。简要讨论了结构活动关系。

  DOI：

  10.1016/s0968-0896(01)00121-3

文献信息

• A Facile Method for the Synthesis of Hydrazine-4-oxothiazolidine and Imino-5-oxothiadiazine Derivatives from 1,4-Disubstituted Thiosemicarbazides
  作者：Alaa A. Hassan、Ashraf A. Aly、Tarek I. M. Bedair、Alan B. Brown、Talaat I. El-Emary

  DOI：10.1002/jhet.1655

  日期：2014.1

  1,4‐Disubstituted thiosemicarbazides reacted with dimethyl acetylenedicarboxylate with formation of (2‐hydrazono‐4‐oxothiazolidin‐5‐ylidene)acetates and, in one case, a (2‐imino‐1,3,4‐thiadiazin‐5‐on‐6‐ylidene)acetate. Several mechanistic options involving nucleophilic interaction are presented. The structures of all newly synthesized compounds were identified by 1H NMR, 13C NMR, COSY, HMQC and HMBC

  1,4-二取代的硫代氨基脲与乙炔二甲酸二甲酯反应生成（2-肼基-4-氧杂噻唑啉-5-吡咯）乙酸酯，在一种情况下还生成（2-亚氨基-1,3,4-噻二嗪-5-酮） -6-亚丙基）乙酸酯。介绍了涉及亲核相互作用的几种机理选择。通过1 H NMR，13 C NMR，COSY，HMQC和HMBC光谱数据鉴定所有新合成的化合物的结构。
• Synthesis and Structure Determination of Substituted Thiazole Derivatives as EGFR/BRAFV600E Dual Inhibitors Endowed with Antiproliferative Activity
  作者：Lamya H. Al-Wahaibi、Essmat M. El-Sheref、Alaa A. Hassan、S. Bräse、M. Nieger、Bahaa G. M. Youssif、Mahmoud A. A. Ibrahim、Hendawy N. Tawfeek

  DOI：10.3390/ph16071014

  日期：——

  a GI50 value of 33 nM. The most potent derivatives were found to be compounds 3a, 3c, 3d, and 3f, with GI50 values ranging from 37 nM to 54 nM. The EGFR-TK and BRAFV600E inhibitory assays’ results matched the antiproliferative assay’s results, with the most potent derivatives, as antiproliferative agents, also being the most potent EGFR and BRAFV600E inhibitors. The docking computations were employed

  2,3,4-三取代噻唑3a-i，在四位有一个甲基，是通过1,4-二取代氨基硫脲与氯丙酮在乙酸乙酯/Et3N中或在回流乙醇中反应合成的。使用核磁共振波谱、质谱和元素分析确定了新化合物的结构。此外，通过X射线分析明确证实了化合物3a的结构。 50 µM 3a-i 的细胞活力测定大于 87%，且所有测试物质均不具有细胞毒性。化合物 3a-i 对四种测试的人类癌细胞系表现出良好的抗增殖活性，GI50 值范围为 37 至 86 nM，而参考厄洛替尼的 GI50 值为 33 nM。发现最有效的衍生物是化合物 3a、3c、3d 和 3f，GI50 值范围为 37 nM 至 54 nM。 EGFR-TK和BRAFV600E抑制测定的结果与抗增殖测定的结果相匹配，作为抗增殖剂的最有效的衍生物也是最有效的EGFR和BRAFV600E抑制剂。对接计算用于研究化合物 3a、3c、3d 和 3f 与 BRAFV600E
• Gold(I) and Silver(I) Complexes Containing Hybrid Sulfonamide/Thiourea Ligands as Potential Leishmanicidal Agents
  作者：Alice P. Borges、Malu M. S. Obata、Silvia H. Libardi、Rafael O. Trevisan、Victor M. Deflon、Ulrich Abram、Francis B. Ferreira、Luiz Antônio S. Costa、Antonio O. T. Patrocínio、Marcos V. da Silva、Júlio C. Borges、Pedro I. S. Maia

  DOI：10.3390/pharmaceutics16040452

  日期：——

  Leishmaniasis is a group of parasitic diseases with the potential to infect more than 1 billion people; however, its treatment is still old and inadequate. In order to contribute to changing this view, this work consisted of the development of complexes derived from MI metal ions with thioureas, aiming to obtain potential leishmanicidal agents. The thiourea ligands (HLR) were obtained by reactions of

  利什曼病是一组寄生虫病，有可能感染超过 10 亿人；然而，其治疗方法仍然陈旧且不充分。为了改变这种观点，这项工作包括开发 MI 金属离子与硫脲的络合物，旨在获得潜在的杀利什曼病剂。硫脲配体 (HLR) 通过对甲苯磺酰肼与 R-异硫氰酸酯反应获得，并用于与 AgI 和 AuI 的络合反应，导致形成 [M(HLR)2]X 组成的络合物（M = Ag 或Au; X = NO3− 或 Cl−)。所有化合物均通过 FTIR、1H NMR、UV-vis、发射光谱和元素分析进行​​表征。一些代表还通过 ESI-MS 和单晶 XRD 进行了研究。通过 DFT 计算进一步分析了它们的性质。评估了它们对 Vero 细胞的细胞毒性以及对婴儿利什曼原虫和巴西利什曼原虫细胞的细胞外杀利什曼原虫活性。此外，还检查了复合物与巴西乳杆菌 (LbOYE) 的老黄酶的相互作用。生物学测试表明，部分化合物具有显着的杀利什曼原虫
• Silberg; Proinov, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1959, vol. 10, p. 329,332
  作者：Silberg、Proinov

  DOI：——

  日期：——
• SHARMA, M. P.;UPADHYAYA, J. S.;SRIVASTAVA, S. P.;SWAMI, R. K., INDIAN J. PHARM. SCI., 1981, 43, N 5, 177-179
  作者：SHARMA, M. P.、UPADHYAYA, J. S.、SRIVASTAVA, S. P.、SWAMI, R. K.

  DOI：——

  日期：——