N'-(1-(6-(N-(1-Piperidinylcarbothioyl)ethanehydrazonoyl)-2-pyridinyl)ethylidene)-1-piperidinecarbothiohydrazide

• 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: N'-(1-(6-(N-(1-Piperidinylcarbothioyl)ethanehydrazonoyl)-2-pyridinyl)ethylidene)-1-piperidinecarbothiohydrazide
• 英文别名: N-[(E)-1-[6-[(Z)-C-methyl-N-(piperidine-1-carbothioylamino)carbonimidoyl]pyridin-2-yl]ethylideneamino]piperidine-1-carbothioamide
• 化学式: C₂₁H₃₁N₇S₂
• 分子量: 445.656
• InChiKey: LWTRMNOCLPQUEK-JVBWRSBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-(1-(6-(N-(1-Piperidinylcarbothioyl)ethanehydrazonoyl)-2-pyridinyl)ethylidene)-1-piperidinecarbothiohydrazide 在 O₂ 作用下， 以 二氯甲烷 、 硝基苯 为溶剂， 生成
  参考文献：
  名称：

  Stoichiometry, products and kinetics of oxidation of neutral 2,6-diacetylpyridine-bis(N4-azacyclic thiosemicarbazone)cobalt(II) complexes by dioxygen in aprotic solvents

  摘要：

  Low-spin, square planar cobalt(II) complexes are obtained by reaction of equimolar cobalt(II) acetate with potentially five-coordinate 2,6-diacetylpyridine-bis(N4-azacyclic thiosemicarbazone) ligands. When the N4-azacyclic moiety is piperidyl, morpholyl and N-methylpiperazyl, the cobalt(II) complexes are abbreviated as [Co(DAPP)], [Co(DAPM)] and [Co(DAPN)], respectively. The complexes are freely soluble in methylene chloride and nitrobenzene. They rapidly react with dioxygen in these solvents to form the corresponding diamagnetic mu-peroxodicobalt(III) complexes with stoichiometry 2Co(II) + O2 --> (Co(III))2O2, as indicated by manometric oxygen uptake, cryoscopic measurements in nitrobenzene and the appearance of a v(O-O) band at 860 cm-1. Comparison of the infrared spectra of the cobalt(II) and cobalt(III) complexes and the H-1 NMR spectra of cobalt(III) complexes with corresponding data for the structurally known nickel(II) complex [Ni(DAPM)] indicates that the bis-thiosemicarbazone ligands act as dibasic tetradentate molecules. However, cobalt is unsymmetrically bonded to the thiohydrazone portions of the ligand. Reduction of dioxygen to bound peroxide by large excesses of these cobalt(II) complexes in nitrobenzene and methylene chloride is governed by the third-order rate law d[(Co(III))2O2]/dt = k2[co(II)]2[O2]. Very negative DELTA-S2#, small DELTA-H2# and minimal solvent effects suggest that assembly of the activated complex is rate-determining. Rate constants k2 at 25-degrees-C decrease in order [Co(DAPN)] > [Co(DAPM] > [Co(DAPP)].

  DOI：

  10.1016/s0020-1693(00)83070-4
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 在 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 2.0h， 生成 N'-(1-(6-(N-(1-Piperidinylcarbothioyl)ethanehydrazonoyl)-2-pyridinyl)ethylidene)-1-piperidinecarbothiohydrazide
  参考文献：
  名称：

  Cytotoxic activity of expanded coordination bis-thiosemicarbazones and copper complexes thereof

  摘要：

  A series of bis-thiosemicarbazone agents with coordinating groups capable of multiple metal coordination modes has been generated and evaluated for potential cytotoxic effects against melanoma (MelRm) and breast adenocarcinoma (MCF-7) cell lines. The bis-thiosemicarbazones in this study generally demonstrated superior cytotoxic activity against MelRm than MCF-7 in the absence of metal ion supplementation, but in most cases could not be considered superior to the reference thiosemicarbazone Dp44mT. The key structural features for the cytotoxic activity were the central metal binding atom on the aromatic core, the thiocarbonyl residue and the nature of substitution on the N4-terminus in terms of size and lipophilicity. The cytotoxicity of bis-thiosemicarbazone ligands improved significantly with Cu(II) supplementation, particularly against MCF-7 cells. The mechanism of cytotoxicity of bis-thiosemicarbazones was proposed to be dependent on the combined effect of metal mobilisation and ROS generation which is so called a "double-punch effect".

  DOI：

  10.1007/s00775-016-1390-7

文献信息

• 以2，6-二乙酰基吡啶缩氨基硫脲为配体的锌化合物及其合成方法和应用
  申请人：广西师范大学

  公开号：CN107698495A

  公开（公告）日：2018-02-16

  本发明公开了一种以2，6‑二乙酰基吡啶缩氨基硫脲为配体的锌化合物及其合成方法和应用，该锌化合物是合成了六个以2，6‑二乙酰基吡啶缩氨基硫脲为配体的Zn配合物，并对该锌化合物进行了的抗肿瘤活性实验，证明其具有抗肿瘤的作用。本发明合理利用金属活性中心和具有抗肿瘤活性化合物的双重作用机理，创新地发展高效、多靶点抗肿瘤金属药物，与常用的抗肿瘤药物顺铂相比，锌配合物的活性更高效，并且锌配合物对人胚肺成纤维细胞WI38活性低，锌还可以调节许多细胞过程，作为辅酶因子和蛋白的活性中心，对于超过300种酶类和许多大分子物质来说是必不可少。
• Cytotoxic activity of expanded coordination bis-thiosemicarbazones and copper complexes thereof
  作者：Fady N. Akladios、Scott D. Andrew、Christopher J. Parkinson

  DOI：10.1007/s00775-016-1390-7

  日期：2016.12

  A series of bis-thiosemicarbazone agents with coordinating groups capable of multiple metal coordination modes has been generated and evaluated for potential cytotoxic effects against melanoma (MelRm) and breast adenocarcinoma (MCF-7) cell lines. The bis-thiosemicarbazones in this study generally demonstrated superior cytotoxic activity against MelRm than MCF-7 in the absence of metal ion supplementation, but in most cases could not be considered superior to the reference thiosemicarbazone Dp44mT. The key structural features for the cytotoxic activity were the central metal binding atom on the aromatic core, the thiocarbonyl residue and the nature of substitution on the N4-terminus in terms of size and lipophilicity. The cytotoxicity of bis-thiosemicarbazone ligands improved significantly with Cu(II) supplementation, particularly against MCF-7 cells. The mechanism of cytotoxicity of bis-thiosemicarbazones was proposed to be dependent on the combined effect of metal mobilisation and ROS generation which is so called a "double-punch effect".
• Stoichiometry, products and kinetics of oxidation of neutral 2,6-diacetylpyridine-bis(N4-azacyclic thiosemicarbazone)cobalt(II) complexes by dioxygen in aprotic solvents
  作者：Ahmed El-Toukhy

  DOI：10.1016/s0020-1693(00)83070-4

  日期：1991.2

  Low-spin, square planar cobalt(II) complexes are obtained by reaction of equimolar cobalt(II) acetate with potentially five-coordinate 2,6-diacetylpyridine-bis(N4-azacyclic thiosemicarbazone) ligands. When the N4-azacyclic moiety is piperidyl, morpholyl and N-methylpiperazyl, the cobalt(II) complexes are abbreviated as [Co(DAPP)], [Co(DAPM)] and [Co(DAPN)], respectively. The complexes are freely soluble in methylene chloride and nitrobenzene. They rapidly react with dioxygen in these solvents to form the corresponding diamagnetic mu-peroxodicobalt(III) complexes with stoichiometry 2Co(II) + O2 --> (Co(III))2O2, as indicated by manometric oxygen uptake, cryoscopic measurements in nitrobenzene and the appearance of a v(O-O) band at 860 cm-1. Comparison of the infrared spectra of the cobalt(II) and cobalt(III) complexes and the H-1 NMR spectra of cobalt(III) complexes with corresponding data for the structurally known nickel(II) complex [Ni(DAPM)] indicates that the bis-thiosemicarbazone ligands act as dibasic tetradentate molecules. However, cobalt is unsymmetrically bonded to the thiohydrazone portions of the ligand. Reduction of dioxygen to bound peroxide by large excesses of these cobalt(II) complexes in nitrobenzene and methylene chloride is governed by the third-order rate law d[(Co(III))2O2]/dt = k2[co(II)]2[O2]. Very negative DELTA-S2#, small DELTA-H2# and minimal solvent effects suggest that assembly of the activated complex is rate-determining. Rate constants k2 at 25-degrees-C decrease in order [Co(DAPN)] > [Co(DAPM] > [Co(DAPP)].