1-p-Toluenesulfonyl-4-cyclohexyl-3-thiosemicarbazide | 97319-65-8

• 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-Toluenesulfonyl-4-cyclohexyl-3-thiosemicarbazide
• 英文别名: p-Toluolsulfonyl-4-cyclohexyl-3-thiosemicarbazid；N-cyclohexyl-2-[(4-methylphenyl)sulfonyl]hydrazinecarbothioamide；1-cyclohexyl-3-[(4-methylphenyl)sulfonylamino]thiourea
• CAS: 97319-65-8
• 化学式: C₁₄H₂₁N₃O₂S₂
• 分子量: 327.472
• InChiKey: VSEXCOQVCMUTTI-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  464.6±38.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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) 、 1-p-Toluenesulfonyl-4-cyclohexyl-3-thiosemicarbazide 以 乙醇 为溶剂， 反应 2.0h， 以87.2%的产率得到chlorido(N-cyclohexyl-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

文献信息

• Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbo­thioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives
  作者：Alaa Hassan、Nasr Mohamed、Kamal El-Shaieb、Hendawy Tawfeek、Stefan Bräse、Martin Nieger

  DOI：10.1055/s-0036-1588179

  日期：2017.8

  othioamides react with 2,3-dichloro-1,4-naphthoquinone to give a series of unprecedented 3-amino- and 3-(alkylamino)-1-phenyl-1H-benzo[f]indazole-4,9-diones in good yields. On the other hand, the reaction of N-substituted 2-tosylhydrazinecarbothioamides with 2,3-dichloro-1,4-naphthoquinone afforded (Z)-N-[3-(tosylamino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-2(3H)-ylidene]-substituted aminium chlorides

  摘要 N-未取代和N-取代的2-苯基肼甲硫基酰胺与2,3-二氯-1,4-萘醌反应生成一系列前所未有的3-氨基-和3-（烷基氨基）-1-苯基-1 H-苯并[ f] ]吲唑-4，9-二酮，收率高。另一方面，N-取代的2-甲苯磺酰氨基甲硫酰胺与2，3-二氯-1，4-萘醌的反应得到（Z）-N- [3-（甲苯磺酰氨基）-4，9-二氧代-4，9-二氢萘并[2,3 - d ]噻唑-2（3 H）-亚烷基]-取代的氯化铵和（Z）-N -[（2-取代的亚氨基）-4,9-dioxo-4,9-二氢萘并[2] ，3- d ]噻唑-3（2 H）-基] -4-甲苯磺酰胺水合物。 N-未取代和N-取代的2-苯基肼甲硫基酰胺与2,3-二氯-1,4-萘醌反应生成一系列前所未有的3-氨基-和3-（烷基氨基）-1-苯基-1 H-苯并[ f] ]吲唑-4，9-二酮，收率高。另一方面，N-取代的2-甲苯磺酰氨基甲硫酰胺与2，3-二氯-1，4-萘醌的反应得到（Z）-N-
• 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
• Cu(I) complexes with thiosemicarbazides derived from p-toluenesulfohydrazide: Structural, luminescence and biological studies
  作者：Alice P. Borges、Zumira A. Carneiro、Fernando S. Prado、Jhonathan R. Souza、Leonardo H. Furlan e Silva、Carolina G. Oliveira、Victor M. Deflon、Sérgio de Albuquerque、Natália Bueno Leite、Antonio E.H. Machado、Antonio O.T. Patrocinio、Pedro I.S. Maia

  DOI：10.1016/j.poly.2018.08.013

  日期：2018.11

  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.