2-thioxo-5-((Z)-2-pyridylmethylidene)imidazol-4-one | 69580-25-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-thioxo-5-((Z)-2-pyridylmethylidene)imidazol-4-one
• 英文别名: 5-pyridine-2-ylmethylene-2-thiooxo-4-imidazolidinone；5-(2-pyridylmethylene)-2-thioxoimidazolidin-4-one；5-(2-pyridylmethylene)-2-thiohydantoin；5-[(Z)-2-pyridylmethylidene]-2-thioxoimidazolidin-4-one；(5Z)-5-(pyridin-2-ylmethylene)-2-thioxoimidazolidin-4-one；(Z)-5-(pyridin-2-ylmethylene)-2-thioxoimidazolidin-4-one；5-(2-Pyridylmethylidene)-2-thio-3,5-dihydro-4h-imidazol-4-one；(5Z)-5-(pyridin-2-ylmethylidene)-2-sulfanylideneimidazolidin-4-one
• CAS: 69580-25-2
• 化学式: C₉H₇N₃OS
• 分子量: 205.24
• InChiKey: DRMFCOHNVXPTHL-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thioxo-5-((Z)-2-pyridylmethylidene)imidazol-4-one 以 氘代二甲亚砜 为溶剂， 生成 5-(pyridin-2-ylmethylene)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  硫酸和氧代咪唑啉衍生物：合成，抗氧化活性和光介导的抗菌活性。

  摘要：

  具有不同环外取代基的咪唑啉衍生物可以简单地从常见的起始原料制备。该程序以环保的方式进行。这些衍生物的抗氧化活性通过不同的实验测定方法进行了探索，例如ABTS。+和DPPH。清除测定以及降低功率测定。根据结果​​讨论结构差异。含硫类似物显示出比其含氧同类物更高的抗氧化活性。在微生物学研究中观察到了相同的趋势，其中分析了相同的咪唑啉化合物对金黄色葡萄球菌和大肠杆菌菌株的光介导活性。暴露于UV-A（400-320 nm）光后，几乎所有硫酸化的咪唑啉均观察到光增强活性。

  DOI：

  10.1002/cmdc.202000048
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-硫代乙内酰脲 在 碳酸氢钠 作用下， 反应 1.33h， 以59%的产率得到2-thioxo-5-((Z)-2-pyridylmethylidene)imidazol-4-one
  参考文献：
  名称：

  硫酸和氧代咪唑啉衍生物：合成，抗氧化活性和光介导的抗菌活性。

  摘要：

  具有不同环外取代基的咪唑啉衍生物可以简单地从常见的起始原料制备。该程序以环保的方式进行。这些衍生物的抗氧化活性通过不同的实验测定方法进行了探索，例如ABTS。+和DPPH。清除测定以及降低功率测定。根据结果​​讨论结构差异。含硫类似物显示出比其含氧同类物更高的抗氧化活性。在微生物学研究中观察到了相同的趋势，其中分析了相同的咪唑啉化合物对金黄色葡萄球菌和大肠杆菌菌株的光介导活性。暴露于UV-A（400-320 nm）光后，几乎所有硫酸化的咪唑啉均观察到光增强活性。

  DOI：

  10.1002/cmdc.202000048

文献信息

• Privileged Scaffolds or Promiscuous Binders: A Comparative Study on Rhodanines and Related Heterocycles in Medicinal Chemistry
  作者：Thomas Mendgen、Christian Steuer、Christian D. Klein

  DOI：10.1021/jm201243p

  日期：2012.1.26

  campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed

  罗丹宁和具有多个杂原子的相关五元杂环最近因在筛选活动中表现为“频繁的杀手”而成为非选择性化合物，因此在药物发现中几乎没有价值。但是，这种判断似乎主要是基于轶事证据。在筛选活动中鉴定出多种罗丹宁和相关化合物后，我们决定对它们的滥交进行系统的研究。合成了163种罗丹宁，乙内酰脲，硫代乙内酰脲和噻唑烷二酮，并针对几个目标进行了测试。还针对聚集和亲电反应性对化合物进行了表征，并分析了罗丹宁与相关化合物在已发表的X射线共晶结构中的结合模式。结果表明，环外，若丹宁和硫代乙内酰脲中的双键硫原子除具有其他结构特征外，还为极性相互作用和氢键提供了特别高的相互作用位点密度。这会导致“筛选范围”内浓度的混杂行为，但不应视为将此类筛选命中排除在进一步开发之外的一般剔除标准。建议将针对靶标亲和力和选择性的特殊标准应用于这些类型的化合物，并因此以有用的方式利用其特殊和潜在有价值的生物分子结合特性。这会导致“筛选范围”
• 5-(Pyridylmethylidene)-substituted 2-thiohydantoins and their complexes with CuII, NiII, and CoII: Synthesis, electrochemical study, and adsorption on the cystamine-modified gold surface
  作者：E. K. Beloglazkina、A. G. Majouga、I. V. Yudin、N. A. Frolova、N. V. Zyk、V. D. Dolzhikova、A. A. Moiseeva、R. D. Rakhimov、K. P. Butin

  DOI：10.1007/s11172-006-0371-3

  日期：2006.6

  A series of CuII, NiII, and CoII complexes with 5-(pyridylmethylidene)-substituted 2-thiohydantoins (L) were synthesized by the reactions of the corresponding organic ligands with MCl2·nH2O. The resulting complexes have the composition LMCl2 (M = Cu or Ni) or L2MCl2 (M = Co). The reactions with N(3)-unsubstituted thiohydantoins afford complexes containing four-membered metallacycles, in which the metal ion is coordinated by the S and N(3) atoms of the thiohydantoin ligand. The reactions of N(3)-substituted thiohydantoins give complexes in which the S and N(1) atoms are involved in coordination. Study by IR spectroscopy demonstrated that the pyridine nitrogen atom is not involved in coordination. Based on the results of electrochemical study of the ligands and complexes by cyclic voltammetry and calculation of their frontier orbitals by the PM3(tm) method, the mechanism of oxidation and reduction of these compounds was proposed. In the first reduction and oxidation steps, the metal atom in the copper and nickel complexes remains, apparently, intact, and these processes occur with the involvement of the ligand fragments, viz., the coordinated thiohydantoin ligand and chloride anion, respectively. In the cobalt complexes, the first reduction step occurs at the ligand; the first oxidation state, at the metal atom. Measurements of the contact angle of aqueous wetting and electrochemical study demonstrated that carboxy-containing 2-thiohydantoins and their complexes can be adsorbed on the cystamine-modified gold surface. The structures of the complexes on the surface differ from the structures of these complexes in solution.

  通过相应的有机配体与 MCl2-nH2O 的反应，合成了一系列具有 5-（吡啶亚甲基）取代的 2-硫代海因（L）的 CuII、NiII 和 CoII 配合物。所得复合物的成分为 LMCl2（M = Cu 或 Ni）或 L2MCl2（M = Co）。与 N(3)-未取代的硫代海因的反应可得到含有四元金属环的配合物，其中金属离子由硫代海因配体的 S 原子和 N(3) 原子配位。N(3) 取代的硫代海因反应生成的配合物中，S 原子和 N(1) 原子参与配位。红外光谱研究表明，吡啶氮原子不参与配位。根据配体和配合物的循环伏安电化学研究结果以及 PM3(tm) 方法对其前沿轨道的计算，提出了这些化合物的氧化和还原机理。在第一个还原和氧化步骤中，铜和镍配合物中的金属原子显然保持完好无损，这些过程分别是在配体片段（即配位的硫代海因配体和氯阴离子）的参与下发生的。在钴配合物中，第一个还原步骤发生在配体上；第一个氧化态发生在金属原子上。水润湿接触角的测量和电化学研究表明，含羧基的 2-硫代海因及其配合物可以吸附在胱胺素修饰的金表面。表面络合物的结构与这些络合物在溶液中的结构不同。
• Syntheses and characterization of 5-substituted hydantoins and thiazolines—implications for crystal engineering of hydrogen bonded assemblies. Crystal structures † of 5-(2-pyridylmethylene)hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin †
  作者：Mubarik M. Chowdhry、D. Michael P. Mingos、Andrew J. P. White、David J. Williams

  DOI：10.1039/b004312p

  日期：——

  bidentate ligands to metal centres whilst retaining on their periphery a range of groups capable of forming triple hydrogen bonds. Their metal complexes have the potential to display interesting magnetic, optical and electrochemical properties when the hydrogen bonds are used for the crystal engineering of solid state materials. Here we report the synthesis and characterization of the six closely related

  一系列六个潜在的双齿 配体描述了由具有亚甲基吡啶基取代基的5元杂环组成的环。这些分子可能是双功能的，充当双齿配体金属中心，同时在其外围保留了能够形成三氢键的一系列基团。当氢键用于固态材料的晶体工程时，它们的金属络合物具有显示出令人感兴趣的磁性，光学和电化学性质的潜力。在这里，我们报告了六个密切相关的分子的合成和表征，5-（2-吡啶基亚甲基）乙内酰脲 我，5-（2-吡啶基亚甲基）-2-硫代乙内酰脲 二，5-（2-吡啶基亚甲基）噻唑烷-2,4-二酮 三，5-（2-吡啶基亚甲基）若丹宁 IV，5-（2-吡啶基亚甲基）假硫代乙内酰脲V和5-（2-吡啶基亚甲基）-2-亚氨基-4-氨基-2,5-二氢噻唑 六。I–VI的固态结构已使用自然丰度固态进行了研究15 N NMR光谱并讨论了I – V的单晶结构。
• Synthesis and electrochemical study of complexes of 2-methylthio-5-(pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-ones with transition metals (Co, Ni, and Cu). Molecular structures of CuIIL1Cl2 (L1 is (5Z)-2-methylthio-3-phenyl-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one) and CoIIL2Cl2 (L2 is (5Z )-3-methyl-2-methylthio-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one)
  作者：E. K. Beloglazkina、S. Z. Vatsadze、A. G. Majouga、N. A. Frolova、R. B. Romashkina、N. V. Zyk、A. A. Moiseeva、K. P. Butin

  DOI：10.1007/s11172-006-0190-6

  日期：2005.12

  New transition metal (NiII, CoII, and CuII) complexes with 2-methylthio-5-(pyridyl-methylidene)-3,5-dihydro-4H-imidazol-4-ones were synthesized by the reaction of 5-(α-, β-, or γ-)pyridyl-substituted 2-methylthio-3,5-dihydro-4H-imidazol-4-ones with MCl2· nH2O. In the complexes with α-Py-substituted ligands, the metal atom has a tetrahedral coordination environment and is coordinated by the nitrogen atoms of the pyridine and thiohydantoin rings and two chloride anions. The results of electronic spectroscopy and magnetic susceptibility measurements suggest that the complexes with the β-and γ-Py-substituted ligands have polymeric structures, and the metal atoms in these complexes are in an octahedral environment. The molecular and crystal structures of CuIIL1Cl2 (L1 is (5Z)-2-methylthio-3-phenyl-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one) and CoIIL2Cl2 (L2 is (5Z)-3-methyl-2-methylthio-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one) were established by X-ray diffraction. Semiempirical quantum-chemical calculations were performed for 2-methylthio-5-(pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-ones. The complexes, starting ligands, and metal chlorides were studied electrochemically. The mechanism of electro-oxidation and electroreduction of 2-methylthio-5-(pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-ones and their cobalt, nickel, and copper complexes was proposed.

  通过 5-(α-、β- 或 γ-)吡啶基取代的 2-甲硫基-3,5-二氢-4H-咪唑-4-酮与 MCl2- nH2O 的反应，合成了新的过渡金属（NiII、CoII 和 CuII）与 2-甲硫基-5-(吡啶基-亚甲基)-3,5-二氢-4H-咪唑-4-酮的配合物。在 α-Py 取代配体的配合物中，金属原子具有四面体配位环境，并由吡啶和硫代海因环的氮原子以及两个氯阴离子配位。电子能谱和磁感应强度测量结果表明，β 和 γ-Py 取代配体的配合物具有聚合结构，这些配合物中的金属原子处于八面体环境中。通过 X 射线衍射建立了 CuIIL1Cl2（L1 为 (5Z)-2-甲硫基-3-苯基-5-(α-吡啶基亚甲基)-3,5-二氢-4H-咪唑-4-酮）和 CoIIL2Cl2（L2 为 (5Z)-3-甲基-2-甲硫基-5-(α-吡啶基亚甲基)-3,5-二氢-4H-咪唑-4-酮）的分子和晶体结构。对 2-甲硫基-5-(吡啶基亚甲基)-3,5-二氢-4H-咪唑-4-酮进行了半经验量子化学计算。对配合物、起始配体和金属氯化物进行了电化学研究。提出了 2-甲硫基-5-（吡啶亚甲基）-3,5-二氢-4H-咪唑-4-酮及其钴、镍和铜配合物的电氧化和电还原机制。
• A multicomponent reaction efficiently producing arylmethylene 2-thiohydantoins
  作者：Sharad Porwal、Rishi Kumar、Prakas R. Maulik、Prem M.S. Chauhan

  DOI：10.1016/j.tetlet.2006.06.076

  日期：2006.8

  We describe here a multicomponent reaction that converts aryl/heteroaryl aldehydes efficiently into arylmethylene 2-thiohydantoins. 3-Formylindole behaves exceptionally giving a gem-diacetylthio derivative. A mechanistic study of the behaviour of 3-formylindole, which provides a new class of indole derivative, is described. (c) 2006 Elsevier Ltd. All rights reserved.