4-苯基-5-(2-噻吩基)-4H-1,2,4-三唑-3-硫氢化合物 | 57600-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-苯基-5-(2-噻吩基)-4H-1,2,4-三唑-3-硫氢化合物
• 英文名称: 4-phenyl-5-(thien-2-yl)-4H-3-mercapto-1,2,4-triazole
• 英文别名: 4-phenyl-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione；3-Mercapto-4-phenyl-5-(2'-thienyl)-1,2,4-thiazol；4-phenyl-3-thiophen-2-yl-1H-1,2,4-triazole-5-thione
• CAS: 57600-04-1
• 化学式: C₁₂H₉N₃S₂
• mdl: MFCD02854429
• 分子量: 259.356
• InChiKey: SCZDETZAWGOQLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  88
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-苯基-5-(2-噻吩基)-4H-1,2,4-三唑-3-硫氢化合物 在 氯 作用下， 以 氯仿 为溶剂， 生成 3-<2'-(5'-Chlorothienyl)>-4-phenyl-5-chloro-1,2,4-triazol
  参考文献：
  名称：

  Nath,T.G. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15, p. 341 - 346

  摘要：

  DOI：
• 作为产物：
  描述：

  N-phenyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-苯基-5-(2-噻吩基)-4H-1,2,4-三唑-3-硫氢化合物
  参考文献：
  名称：

  Chemical and Pharmacological Properties of 3-(Thiophen-2-yl)-4-substituted-Δ²-1,2,4-triazoline-5-thiones

  摘要：

  Three 3-(thiophen-2-yl)-4-substituted-Delta(2)-1,2,4-triazoline-5-thiones were synthesized by intramolecular cyclization of 1-(thiophen-2-ylcarbonyl)-4-substituted thiosemicarbazides in alkaline medium. Their effects on the central nervous system (CNS) of mice in some behavioral tests were investigated. All investigated compounds displayed antinociceptive activity. The correlation between the structural features and bioactivity has been discussed.

  DOI：

  10.1080/10426500801968136

文献信息

• Design, Synthesis, and Structure−Activity Relationship of Substrate Competitive, Selective, and in Vivo Active Triazole and Thiadiazole Inhibitors of the c-Jun N-Terminal Kinase
  作者：Surya K. De、John L. Stebbins、Li-Hsing Chen、Megan Riel-Mehan、Thomas Machleidt、Russell Dahl、Hongbin Yuan、Aras Emdadi、Elisa Barile、Vida Chen、Ria Murphy、Maurizio Pellecchia

  DOI：10.1021/jm801503n

  日期：2009.4.9

  We report comprehensive structure−activity relationship studies on a novel series of c-Jun N-terminal kinase (JNK) inhibitors. The compounds are substrate competitive inhibitors that bind to the docking site of the kinase. The reported medicinal chemistry and structure-based optimizations studies resulted in the discovery of selective and potent thiadiazole JNK inhibitors that display promising in

  我们报告了一系列新型 c-Jun N 末端激酶 (JNK) 抑制剂的综合构效关系研究。这些化合物是与激酶对接位点结合的底物竞争性抑制剂。报道的药物化学和基于结构的优化研究导致发现了选择性和有效的噻二唑 JNK 抑制剂，这些抑制剂在胰岛素不敏感的小鼠模型中显示出有希望的体内活性。
• [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。
• 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。
• Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain
  作者：Ashot S. Saghyan、Hayarpi M. Simonyan、Satenik G. Petrosyan、Anna F. Mkrtchyan、Lilit V. Khachatryan、Arpine V. Geolchanyan、Melanya A. Samvelyan、Tariel V. Ghochikyan、Nazken Kelzhanova、Amanzhan T. Saginayev、Peter Langer

  DOI：10.5560/znb.2014-3221

  日期：2014.4.1

  An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

  报告了一种高效的方法，用于不对称合成侧链中含有呋喃基和噻吩基取代的三唑的 a-氨基酸。该策略依赖于 3,4,5-取代的 1,2,4-三唑与含有由脱氢氨基酸（脱氢丙氨酸和 (E + Z)- 脱氢氨基丁酸）和手性助剂（即 (S)-2-N- N,N,N-三唑）形成的希夫碱的手性 NiII 复合物的 C=C 键的迈克尔加成。即(S)-2-N-(N0-苄基)氨基二苯甲酮和(S)-2-N-(N0-2-氯苄基)氨基二苯甲酮。这些反应的非对映选择性良好。水解非对映异构体混合物金属络合物可得到对映异构体纯度高（ee> 98%）的 a-氨基酸。
• Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones
  作者：Qing-Hu Teng、Feng-Lai Lu、Kai Wang、Li-Ya Zhou、Dian-Peng Li

  DOI：10.1021/acs.joc.3c00320

  日期：2023.6.2

  A photocatalytic chemodivergent reaction for the selectivity formation of C–S and C–N bonds in a controlled manner was proposed. The reaction medium, either neutral or acidic, is critical to dictate the formation of 2-amino-1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones from isothiocyanates and hydrazones. This is a practical protocol to achieve the chemoselectivity under mild and metal-free conditions

  提出了一种以受控方式选择性形成 C-S 和 C-N 键的光催化化学发散反应。中性或酸性反应介质对于决定从异硫氰酸酯和腙形成 2-氨基-1,3,4-噻二唑和 1,2,4-三唑-3-硫酮至关重要。这是在温和和无金属条件下实现化学选择性的实用方案。