4-phenyl-3-(4-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thion | 26028-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-3-(4-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thion
• 英文别名: 5-(4-hydroxyphenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione；3-(4-hydroxyphenyl)-4-phenyl-1H-1,2,4-triazole-5(4H)-thion；2,4-dihydro-5-(4-hydroxyphenyl)-4-phenyl-3H-1,2,4-triazole-3-thione；5-(4-hydroxyphenyl)-2,4-dihydro-4-phenyl-3H-1,2,4-triazol-3-thione；5-(4-hydroxyphenyl)-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione；4-(5-Mercapto-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol；3-(4-hydroxyphenyl)-4-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 26028-88-6
• 化学式: C₁₄H₁₁N₃OS
• 分子量: 269.327
• InChiKey: JGQHFMIKRTUVNL-UHFFFAOYSA-N

物化性质

• 沸点：
  421.3±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-3-(4-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thion 、 四溴甲苯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 0.5h， 以55%的产率得到1,2,4,5-tetrakis[5-(4-hydroxyphenyl)-4-phenyl-1,2,4-triazol-3-ylthiomethyl]benzene
  参考文献：
  名称：

  Synthesis of 1,2,4,5-Tetrakis(1,2,4-Triazolyl) Benzene and 1,2,4,5-Tetrakis(1,3,4-Oxadiazolyl) Benzene Derivatives

  摘要：

  A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to 1,2,4,5-tetrakis(bromomethyl) benzene. The structure of the newly synthesized compounds was confirmed by elemental analysis, IR and H-1 and C-13 NMR spectra.

  DOI：

  10.1080/10426507.2011.597801
• 作为产物：
  描述：

  4-羟基苯甲酰肼 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 4-phenyl-3-(4-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thion
  参考文献：
  名称：

  Synthesis and Tuberculostatic Activity of Some 2-Piperazinmethylene Derivatives 1,2,4-Triazole-3-Thiones

  摘要：

  The Mannich. reaction's products of 1,2,4-triazole-3-thiones, substituted in position 4 (with ethyl, allyl, phenyl, Ph-4-Br) or 5 (with phenyl, Ph-4-OH, Ph-3,4,5-(OMe)(3), 2-phenyl) were obtained. Their amino-components were 1-phenylpiperazine, 1-(4-fluorophenyl)-piperazine, 1-benzylpiperazine, 1-(2-pyridyl)-piperazine and 1-piperonyl-piperazine. Tuberculostatic activity of the compounds obtained was tested in vitro and their MIC values within 25-100 mcg/mL.

  DOI：

  10.1080/104265090517280

文献信息

• [EN] USE OF DERIVATIVES OF 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONE AS INHIBITORS O FTEH ENZYME MYELOPEROXIDASE (MPO)<br/>[FR] UTILISATION DE DERIVES DE 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONES COMME INHIBITEURS DE L'ENZYME MYELOPEROXYDASE (MPO)
  申请人：ASTRAZENECA AB

  公开号：WO2004096781A1

  公开（公告）日：2004-11-11

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  揭示了使用公式(I)中X、Y、W和Q如规范中定义的化合物及其药用盐，在制造药物中用于治疗或预防对髓过氧化物酶（MPO）抑制有益的疾病或症状。公开了某些公式(I)的新化合物及其药用盐，以及它们的制备方法。公式(I)的化合物是MPO抑制剂，因此在治疗或预防神经炎症性疾病中特别有用。
• Solid-Phase Synthesis of 4,5-Disubstituted-1,2,4-triazole-3-thione Derivatives Based on the Resin-Bound Acylhydrazines
  作者：Zhanxiang Liu、Yunrui Yi、Jinlong Zhao、Mingxue Tang

  DOI：10.1080/00397911.2010.521609

  日期：2012.1.1

  Abstract Highly efficient solid-phase synthesis of 4,5-disubstituted-1,2,4-triazole-3-thiones under mild conditions has been developed. 4,5-Disubstituted-1,2,4-triazole-3-thione derivatives were synthesized from resin-bound acylhydrazines in several steps, providing 76–89% overall yields and excellent purity. GRAPHICAL ABSTRACT

  摘要 已开发出在温和条件下高效固相合成 4,5-二取代-1,2,4-三唑-3-硫酮。4,5-二取代-1,2,4-三唑-3-硫酮衍生物是由树脂结合的酰基肼分几个步骤合成的，总产率为76-89%，纯度极佳。图形概要
• Use of derivatives of 2, 4-dihydro-[1,2,4] triazole-3-thione as inhibitors of the enzyme myeloperoxidase (mpo)
  申请人：Svensson Mats

  公开号：US20070093483A1

  公开（公告）日：2007-04-26

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  本发明揭示了使用化合物(I)的使用，其中X、Y、W和Q如规范中所定义，以及其药学上可接受的盐，在制造药物方面，用于治疗或预防抑制髓过氧化物酶（MPO）酶有益的疾病或状况。揭示了某些新型化合物(I)及其药学上可接受的盐，以及其制备方法。化合物(I)的MPO抑制剂，因此特别适用于治疗或预防神经炎症性疾病。
• Certain triazole-based compounds, compositions, and uses thereof
  申请人：Hodge Nicholas Carl

  公开号：US20050288347A1

  公开（公告）日：2005-12-29

  Thiotriazole-based chemical entities exhibiting ATP-utilizing enzyme inhibitory activity, methods of using such chemical entities, and compositions comprising such chemical entities, are described.

  描述了具有 ATP 利用酶抑制活性的硫代三唑类化学实体、使用此类化学实体的方法以及包含此类化学实体的组合物。
• Synthesis of a Series of Novel Tetra-tert-butylcalix[4]arene Linked to 1,2,4-Triazole and 1,3,4-Oxadiazole Derivatives
  作者：Karim Akbari Dilmaghani、Zahra Dono Ghezelbash

  DOI：10.17344/acsi.2016.2637

  日期：2016.12.15

  A series of tetra-tert-butylcalix[4] arene linked to 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones derivatives at lower rim were synthesized by the reaction of 1,2,4-triazole-5-thione and 1,3,4-oxadiazole-5-thione with 5,11,17,23-tetra-tert-butyl-25,27-bis(3-bromopropoxy)-26,28-dihydroxycalix[4] arene (2). The synthesized compounds were characterized by FT-IR, H-1 NMR, C-13 NMR spectral data, elemental analysis and ESI-MS.