8-quinoline aldehyde thiosemicarbazone | 3652-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-quinoline aldehyde thiosemicarbazone
• 英文别名: 2-(quinolin-8-ylmethylene)hydrazine-1-carbothioamide；8-quinolinecarboxaldehyde thiosemicarbazone；8-Quinolinaldehyde thiosemicarbazone；(quinolin-8-ylmethylideneamino)thiourea
• CAS: 3652-39-9
• 化学式: C₁₁H₁₀N₄S
• mdl: MFCD01582792
• 分子量: 230.293
• InChiKey: BLGCVICZLQXPMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 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：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(ll) sulfate pentahydrate 、 8-quinoline aldehyde thiosemicarbazone 以 硫酸 为溶剂， 生成 [Cu(8-quinolinecarboxaldehyde thiosemicarbazone)(SO4)]2
  参考文献：
  名称：

  Synthesis and structure of copper(II) coordination compounds with 8-quinolinecarboxaldehyde thio- and 4-phenylthiosemicarbazones

  摘要：

  8-Quinolinecarboxaldehyde thiosemicarbazone (HL) and copper form compounds with a metal : ligand ratio of 1 : 1 in which the ligand is either the neutral molecule or the monohydric acid anion. Its acidic properties are enhanced not only as a result of coordination but also due to the electronic effect of substituents in the thiosemicarbazide moiety. 8-Quinolinecarboxaldehyde 4-phenylthiosemicarbazone (HL1) is coordinated only as the anion. The structures of [Cu(HL)SO4](2), [Cu(L)NO3](2), and [Cu(L-1)NO3](2) center dot 0.25H(2)O, and free HL1 were studied. The tendency of the complexes to dimerization and association with acid anions or sulfur atoms of the organic ligands as bridges was established. In binuclear compounds with closely spaced magnetic centers, no exchange interaction between them was found. The copper coordination compounds with HL are able to suppress the growth of cancer cells 41M and SK-BR-3 and are promising objects for investigation as anticancer drugs.

  DOI：

  10.1134/s0036023610090093
• 作为产物：
  描述：

  喹啉-8-甲醛 、 氨基硫脲 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到8-quinoline aldehyde thiosemicarbazone
  参考文献：
  名称：

  喹啉衍生物作为潜在的抗结核药物：合成、分子对接和作用机制

  摘要：

  需要开发具有新作用机制的新药来对抗耐药结核分枝杆菌的问题。本研究旨在结合两种药效团（喹啉或异喹啉和氨基硫脲）合成一系列化合物。本研究基于组合原理合成了七种化合物。化合物 1-7 对M. tuberculosis H 37 Rv 菌株具有活性，MIC 值为 2 至 8 μg/ml。化合物5表现出显着的抗分枝杆菌活性（MIC = 2 μg/ml），因此被选择用于作用机​​制的研究。分子对接最初表明化合物5可能占据结核分枝杆菌KatG的活性位点。此外，化合物5对KatG的活性表现出有效的抑制作用。RT-PCR最终显示化合物5可以上调结核分枝杆菌katG的转录。总之，这些研究表明化合物5可能是结核分枝杆菌KatG 的抑制剂。这项研究中出现的一个更重要的发现是结核分枝杆菌的 KatG可以用作新的抗结核药物设计的推定新靶点。

  DOI：

  10.1016/j.micpath.2022.105507

文献信息

• (Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines
  作者：Tamara R. Todorović、Jelena Vukašinović、Gustavo Portalone、Sherif Suleiman、Nevenka Gligorijević、Snezana Bjelogrlić、Katarina Jovanović、Siniša Radulović、Katarina Anđelković、Analisse Cassar、Nenad R. Filipović、Pierre Schembri-Wismayer

  DOI：10.1039/c6md00501b

  日期：——

  A comparative study of (chalcogen)semicarbazones and their cobalt complexes was performed.

  进行了(硫族)半胱氨酮和它们的钴配合物的比较研究。
• Synthesis and structure of new copper(II) coordination compounds with 8-quinoline aldehyde semicarbazones and thiosemicarbazones
  作者：P. N. Bourosh、M. D. Revenko、E. F. Stratulat、B. Wicher、M. Gdaniec、I. D. Korzha

  DOI：10.1134/s0036023614060059

  日期：2014.6

  Copper(II) salts were reacted with various quinoline aldehyde chalcogensemicarbazones to yield compounds formulated as Cu(HL)X-2 center dot nH(2)O (I: HL = quinoline aldehyde thiosemicarbazone (HL1), X = ClO4, n = 2; II: HL = quinoline aldehyde 4-C2H5-thiosemicarbazone (HL1a), X = NO3, n = 0; III: HL = quinoline aldehyde semicarbazone (HL2), X = ClO4, n = 3 and IV: HL = quinoline aldehyde 4-Ph-semicarbazone (HL2a), X = NO3, n = 1). Regardless of the reagent ratio, the products were compounds having the metal: ligand ratio of 1: 1, where the organic ligand was coordinated tridentate in a molecular form. Single-crystal X-ray diffraction showed that, depending on the chalcogen atom in the organic ligand (S or O), the substituent in the 4th position (at the terminal nitrogen atom), and the specifics of the acido ligand, complexes I-IV had appreciably differing molecular structure organizations. The structures of I and III are formed by a 1D charged coordination polymer, ClO (4) (-) anions, and water molecules and may be described by the formula [Cu(HL)(H2O)(ClO4)] (n) (ClO4) (n) center dot nH(2)O. Copper(II) coordination polyhedra in I and II are (4 + 2) and (4 + 1 + 1) tetragonal bipyramids, respectively. In II and IV, the structures are monomeric and can be described as [Cu(HL1a)(NO3)(2)] with the metal coordination polyhedron shaped as a (4 + 1) tetragonal pyramid in II and as [Cu(HL2a)(H2O)(NO3)](NO3) with the metal coordination polyhedron shaped as a (3 + 2) trigonal bipyramid in IV. The structure of II is built of molecular complexes, each comprising, apart from ligand HL1a, two monodentate coordinated NO (3) (-) groups. The oxygen atom of one anion together with the NNS donor atom set of ligand HL1a form the base, and the oxygen atom of the other anion is in the apex of the coordination polyhedron. In IV, the structure is ionic and built of NO (3) (-) anions and [Cu(HL2a)(H2O)(NO3)](+) complex cations, where a cationic coordination polyhedron has a trigonal-bipyramidal configuration with organic ligand HL2a positioned along the long edge. The bipyramidal base is made up by the oxygen atoms of the coordinated water molecule and monodentate nitrato group and the nitrogen atom N2 of the azomethyne group.