2-thioxo-3-methyl-5-((Z)-pyridine-2-ylmethylene)-tetrahydro-4H-imidazole-4-one | 916747-71-2

• 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-3-methyl-5-((Z)-pyridine-2-ylmethylene)-tetrahydro-4H-imidazole-4-one
• 英文别名: 3-methyl-5-[(Z)-2-pyridylmethylidene]-2-thioxoimidazolidin-4-one；3-methyl-2-thioxo-5-((Z)-2-pyridylmethylene)imidazolidin-4-one；3-methyl-5-(2-pyridylmethylene-2-thiohydantoin；(5Z)-3-methyl-5-(pyridin-2-ylmethylidene)-2-sulfanylideneimidazolidin-4-one
• CAS: 916747-71-2
• 化学式: C₁₀H₉N₃OS
• 分子量: 219.267
• InChiKey: DDZJGQSVQONJTH-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  77.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thioxo-3-methyl-5-((Z)-pyridine-2-ylmethylene)-tetrahydro-4H-imidazole-4-one 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成 (Z)-3-methyl-5-(2-pyridylmethylene)hydantoin
  参考文献：
  名称：

  A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS

  摘要：

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.

  DOI：

  10.1080/10426509708043491
• 作为产物：
  描述：

  吡啶-2-甲醛 、 Mth-甘氨酸 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以73%的产率得到2-thioxo-3-methyl-5-((Z)-pyridine-2-ylmethylene)-tetrahydro-4H-imidazole-4-one
  参考文献：
  名称：

  5-(Pyridylmethylidene)-substituted 2-thiohydantoins and their complexes with CuII, NiII, and CoII: Synthesis, electrochemical study, and adsorption on the cystamine-modified gold surface

  摘要：

  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。

  DOI：

  10.1007/s11172-006-0371-3

文献信息

• TELOMERASE INHIBITORS AND A METHOD FOR THE PREPARATION THEREOF
  申请人：UCHREZHDENIE KHIMICHESKIJJ FAKUL'TET GOSUDARSTVENNOE UCHEBNO-NAUCHNOE

  公开号：US20130109861A1

  公开（公告）日：2013-05-02

  The invention relates to the field of organic and medicinal chemistry, and molecular biology, and concerns a method for the preparation of a new class of telomerase-inhibiting compounds, which can be utilized for studying telomerases and catalytic sub-units of telomerases, and reverse transcriptases, and foe studying and treating neoplastic and viral diseases. Telomerase-inhibiting coordination compounds of derivatives of imidazol-4-one are characterized by general formula

  本发明涉及有机化学、药物化学和分子生物学领域，涉及一种制备新型端粒酶抑制剂化合物的方法，可用于研究端粒酶和催化亚单位，以及反转录酶，用于研究和治疗肿瘤和病毒性疾病。咪唑-4-酮衍生物的端粒酶抑制配位化合物的一般式如下：
• Synthesis and electrochemistry of (5Z,5′Z)-2,2′-(alkane-α,ω-diyldisulfanyldiyl)-bis(5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-one) complexes with cobalt(II) chloride
  作者：E. K. Beloglazkina、A. G. Majouga、I. V. Yudin、N. V. Zyk、A. A. Moiseeva、K. P. Butin

  DOI：10.1007/s11172-006-0092-7

  日期：2005.9

  presence of potassium carbonate. Complexes of these compounds (L) with CoCl2 were synthesized. In all cases, the complexes L(CoCl2)2 were formed regardless of the ratio of L and inorganic salt introduced into the reaction. According to electronic spectroscopic data, the cobalt atom in the complexes has a tetrahedral coordination environment. The synthesized ligands and complexes were electrochemically studied

  一系列含有两个 5-(2-pyridylmethylene)-2-sulfanyl-3,5-dihydro-4H-imidazol-4-one 部分的 S-烷基化 2-thiohydantoin 衍生物是通过具有不同碳原子数的多亚甲基桥连接的第一次合成。这些化合物是通过 3-苯基-5-(2-吡啶基亚甲基)-2-硫代乙内酰脲或 3-甲基-5-(2-吡啶基亚甲基)-2-硫代乙内酰脲与不同的 α,ω-二溴烷在丙酮或 DMF 中烷基化得到的在碳酸钾的存在下。合成了这些化合物(L)与CoCl 2 的配合物。在所有情况下，无论引入到反应中的 L 和无机盐的比例如何，都会形成配合物 L(CoCl2)2。根据电子光谱数据，配合物中的钴原子具有四面体配位环境。
• A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS
  作者：Ahmed I. Khodair

  DOI：10.1080/10426509708043491

  日期：1997.3.1

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.
• 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。