2-benzoylpyridine 4-ethyl-3-thiosemicarbazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-benzoylpyridine 4-ethyl-3-thiosemicarbazone
• 英文别名: N-ethyl-2-(phenyl(pyridin-2-yl)methylene)hydrazinecarbothioamide；1-ethyl-3-[(E)-[phenyl(2-pyridyl)methylene]amino]thiourea；1-ethyl-3-[(E)-[phenyl(pyridin-2-yl)methylidene]amino]thiourea
• 化学式: C₁₅H₁₆N₄S
• 分子量: 284.385
• InChiKey: ZKCWDEAIMIMCAK-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylpyridine 4-ethyl-3-thiosemicarbazone 、 copper(I) bromide 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到
  参考文献：
  名称：

  使用 2-苯甲酰基吡啶硫缩氨基脲稳定 CuII-I 键 - 合成、结构、光谱、荧光和循环伏安法

  摘要：

  碘化铜 (I) 与 N1-取代的 2-苯甲酰基吡啶缩氨基硫脲 [(C6H5)(C5H4N)C2=N3–N2H–C(=S)–N1HR (R = Me, HLMe; Et, HLEt; Ph, HLPh )] 在乙腈/二氯甲烷混合物中形成了复合物 [Cu2III2(μ4-N,N,S-LMe)2] (1), [CuIII(κ3-N,N,S-LEt)] (4) 和 [ CuIII(κ3-N,N,S-LPh)] (7) 通过质子耦合电子转移 (PCET)，这些配合物具有罕见的 CuII-I 键。上述硫代配体与溴化铜 (I) 和氯化铜 (I) 也形成了类似的 CuII-Br 和 CuII-Cl 键的化学计量复合物 [CuIIX(κ3-N,N,SL)] (L = LMe, LEt, LPh, X = Br 2, 5, 8; X = Cl 3, 6, 9) 通过 PCET。所有配合物均已通过元素分析、红外光谱、电子吸收光谱、ESR

  DOI：

  10.1002/ejic.201500618
• 作为产物：
  描述：

  2-苯甲酰吡啶 、 4-乙基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以70%的产率得到2-benzoylpyridine 4-ethyl-3-thiosemicarbazone
  参考文献：
  名称：

  使用 2-苯甲酰基吡啶硫缩氨基脲稳定 CuII-I 键 - 合成、结构、光谱、荧光和循环伏安法

  摘要：

  碘化铜 (I) 与 N1-取代的 2-苯甲酰基吡啶缩氨基硫脲 [(C6H5)(C5H4N)C2=N3–N2H–C(=S)–N1HR (R = Me, HLMe; Et, HLEt; Ph, HLPh )] 在乙腈/二氯甲烷混合物中形成了复合物 [Cu2III2(μ4-N,N,S-LMe)2] (1), [CuIII(κ3-N,N,S-LEt)] (4) 和 [ CuIII(κ3-N,N,S-LPh)] (7) 通过质子耦合电子转移 (PCET)，这些配合物具有罕见的 CuII-I 键。上述硫代配体与溴化铜 (I) 和氯化铜 (I) 也形成了类似的 CuII-Br 和 CuII-Cl 键的化学计量复合物 [CuIIX(κ3-N,N,SL)] (L = LMe, LEt, LPh, X = Br 2, 5, 8; X = Cl 3, 6, 9) 通过 PCET。所有配合物均已通过元素分析、红外光谱、电子吸收光谱、ESR

  DOI：

  10.1002/ejic.201500618

文献信息

• [EN] THIOSEMICARBAZONE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS THIOSEMICARBAZONES ET LEUR UTILISATION
  申请人：RICHARDSON DESI RAYMOND

  公开号：WO2010000008A1

  公开（公告）日：2010-01-07

  A method of treating a proliferative disease in a vertebrate, the method comprising administering to the vertebrate a therapeutically effective amount of at least one compound of formula (I) (I) wherein R1 is selected from H, C1-6 alkyl, C2-6 alkenyl and phenyl; R2 is selected from H, C1-6 alkyl, C2-6 alkenyl and phenyl; wherein R1 and R2 are the same or different, or a salt, hydrate, or iron complex thereof, or a pharmaceutical composition comprising said compound, salt, hydrate or iron complex and a pharmaceutically acceptable carrier, diluent or excipient.

  在脊椎动物中治疗增生性疾病的方法，该方法包括向脊椎动物施用至少一种式(I)的化合物的治疗有效量(I)其中R1从H，C1-6烷基，C2-6烯基和苯基中选择；R2从H，C1-6烷基，C2-6烯基和苯基中选择；其中R1和R2相同或不同，或其盐，水合物或铁络合物，或包括所述化合物，盐，水合物或铁络合物以及药学上可接受的载体，稀释剂或赋形剂的药物组合物。
• Novel biotin-functionalized lipidic nanocarriers for encapsulating BpT and Bp4eT iron chelators: evaluation of potential anti-tumour efficacy by in vitro, in vivo and pharmacokinetic studies in A549 mice models
  作者：Shweta Dumoga、Namit Dey、Anivind Kaur、Surendra Singh、Anil K. Mishra、Dipti Kakkar

  DOI：10.1039/c6ra03079c

  日期：——

  This work proposes a novel strategy for delivery of iron chelators to the tumour cells which is exemplified in A549 mice models by using lipidic nanocarriers and introducing biotin based targeting.

  这项工作提出了一种新颖的策略，用于将铁螯合剂传递到肿瘤细胞中，该策略在A549小鼠模型中得到了示范，使用了脂质纳米载体并引入了基于生物素的靶向。
• Synthesis, X-ray crystal structure, DNA/protein binding, DNA cleavage and cytotoxicity studies of N(4) substituted thiosemicarbazone based copper(II)/nickel(II) complexes
  作者：Mathiyan Muralisankar、Jebiti Haribabu、Nattamai S.P. Bhuvanesh、Ramasamy Karvembu、Anandaram Sreekanth

  DOI：10.1016/j.ica.2016.04.043

  日期：2016.8

  (BSA). A DNA cleavage study showed that the complexes cleaved DNA without any external agent. The alterations in the secondary structure of the protein by the ligand and complexes were confirmed by synchronous fluorescence spectroscopic studies. Spectral evidences also showed good binding property of the complexes with the protein. An in vitro cytotoxicity study of the complexes found significant activity

  摘要从4-乙基-3-硫代氨基脲和2-苯甲酰基吡啶制得N-乙基-2-（苯基（吡啶-2-基）亚甲基）肼基碳硫代酰胺（HBpyeTsc）。由HBpyeTsc和[CuCl2·2H2O] / [NiCl2·6H2O]合成了CuBpyeTscCl和Ni [BpyeTsc] 2Cl2。合成的配体和配合物通过分析和各种光谱技术进行表征。配体和配合物的分子结构通过单晶X射线衍射法测定。单晶X射线衍射表明，CuBpyeTscCl和Ni [BpyeTsc] 2Cl2分别表现出方形平面和扭曲的八面体几何形状。研究了所有合成的化合物HBpyeTsc，CuBpyeTscCl和Ni [BpyeTsc] 2Cl2与小牛胸腺DNA（CT DNA）和牛血清白蛋白（BSA）的相互作用。DNA切割研究表明，该复合物在没有任何外部试剂的情况下切割了DNA。同步荧光光谱研究证实了配体和复合物对蛋白质二级结构的改变。光谱证据还表明复合
• Improved cytotoxicity of pyridyl-substituted thiosemicarbazones against MCF-7 when used as metal ionophores
  作者：Fady N. Akladios、Scott D. Andrew、Christopher J. Parkinson

  DOI：10.1007/s10534-015-9905-1

  日期：2016.2

  Zinc is the second most abundant transition metal in the human body, between 3 and 10 % of human genes encoding for zinc binding proteins. We have investigated the interplay of reactive oxygen species and zinc homeostasis on the cytotoxicity of the thiosemicarbazone chelators against the MCF-7 cell line. The cytotoxicity of thiosemicarbazone chelators against MCF-7 can be improved through supplementation of ionic zinc provided the zinc ion is at a level exceeding the thiosemicarbazone concentration. Elimination of the entire cell population can be accomplished with this regime, unlike the plateau of cytotoxicity observed on thiosemicarbazone monotherapy. The cytotoxic effects of copper complexes of the thiosemicarbazone are not enhanced by zinc supplementation, displacement of copper from the complex being disfavoured. Treatment of MCF-7 with uncomplexed thiosemicarbazone initiates post G1 blockade alongside the induction of apoptosis, cell death being abrogated through subsequent supplementation with zinc ion after drug removal. This would implicate a metal depletion mechanism in the cytotoxic effect of the un-coordinated thiosemicarbazone. The metal complexes of the species, however, fail to initiate similar G1 blockade and apparently exert their cytotoxic effect through generation of reactive oxygen species, suggesting that multiple mechanisms of cytotoxicity can be associated with the thiosemicarbazones dependant on the level of metal ion association.
• Copper(II) complexes of 2-benzoylpyridine 4N-substituted thiosemicarbazones
  作者：Douglas X. West、Janeice S. Ives、Jacqueline Krejci、Michelle M. Salberg、Terri L. Zumbahlen、Gordon A. Bain、Anthony E. Liberta、Jesus Valdes-Martinez、Simon Hernandez-Ortiz、Ruben A. Toscano

  DOI：10.1016/0277-5387(95)00010-p

  日期：1995.8

  2-Benzoylpyridine N-4-substituted thiosemicarbazones commonly coordinate as neutral tridentate ligands to give five coordinate [Cu(HL)Cl-2] complexes when prepared in boiling isopropanol. However, when prepared in boiling ethanol, the anion (loss of the N-3-hydrogen) coordinates as a tridentate ligand to give [CuLCl] complexes. Representative crystal structures of both stoichiometries have been determined. Spectral characterization of both the 2-benzoylpyridine N-4-substituted thiosemicarbazones and their copper(II) complexes includes IR, UV-vis, EPR and NMR studies. Growth inhibition studies of the thiosemicarbazones and their complexes were performed against two human pathogenic fungi.