4-乙基-4H-1,2,4-噻唑-3-硫醇 | 27105-98-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇/硫酚
• 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-乙基-4H-1,2,4-噻唑-3-硫醇
• 英文名称: 4-ethyl-2,3-dihydro-4H-1,2,4-triazole-3-thione
• 英文别名: 4-ethyl-2,4-dihydro-[1,2,4]triazole-3-thione；4-Aethyl-2,4-dihydro-[1,2,4]triazol-3-thion；4-Ethyl-1,2,4-triazolin-5-thion；4-ethyl-4H-1,2,4-triazole-3-thiol；4-ethyl-1H-1,2,4-triazole-5-thione
• CAS: 27105-98-2
• 化学式: C₄H₇N₃S
• mdl: MFCD00185955
• 分子量: 129.186
• InChiKey: VYCYFQLHLFRVKW-UHFFFAOYSA-N

物化性质

• 沸点：
  158.0±23.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• WGK Germany：
  3
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4-乙基-4H-1,2,4-噻唑-3-硫醇 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以83%的产率得到methyl 2-((4-ethyl-4H-1,2,4-triazol-3-yl)thio)acetate
  参考文献：
  名称：

  二芳基甲烷骨架的系统构效关系 (SAR) 探索和高效新型尿酸转运蛋白 1 (URAT1) 抑制剂的发现

  摘要：

  为了系统地探索和更好地理解二芳基甲烷骨架在设计强效尿酸转运蛋白 1 (URAT1) 抑制剂时的构效关系 (SAR)，设计并合成了 33 种化合物（1a-1x 和 1ha-1hi），并测定了它们的体外 URAT1 抑制活性 (IC50)。三轮系统的 SAR 探索导致发现了一种高效的新型 URAT1 抑制剂，1h，其效力分别比母体 lesinurad 和苯溴马隆强 200 倍和 8 倍（IC50 = 0.035 μM 对人 URAT1 1 小时 vs lesinurad 和苯溴马隆分别为 7.18 μM 和 0.28 μM）。化合物 1h 是迄今为止我们实验室发现的最有效的 URAT1 抑制剂，也可与目前正在临床试验中开发的最有效的抑制剂相媲美。

  DOI：

  10.3390/molecules23020252
• 作为产物：
  描述：

  异硫氰酸乙酯 在 肼 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 16.25h， 生成 4-乙基-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  Narrow SAR in odorant sensing Orco receptor agonists

  摘要：

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.081

文献信息

• Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X
  作者：Urša Pečar Fonović、Damijan Knez、Martina Hrast、Nace Zidar、Matic Proj、Stanislav Gobec、Janko Kos

  DOI：10.1016/j.ejmech.2020.112218

  日期：2020.5

  Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo [b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 mu M-13.6 mu M. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X. (c) 2020 Published by Elsevier Masson SAS.
• Dobosz, Maria; Pitucha, Monika; Wujec, Monika, Acta poloniae pharmaceutica, 1996, vol. 53, # 1, p. 31 - 38
  作者：Dobosz, Maria、Pitucha, Monika、Wujec, Monika

  DOI：——

  日期：——
• Freund, Chemische Berichte, 1896, vol. 29, p. 2487
  作者：Freund

  DOI：——

  日期：——
• Systematic Structure-Activity Relationship (SAR) Exploration of Diarylmethane Backbone and Discovery of A Highly Potent Novel Uric Acid Transporter 1 (URAT1) Inhibitor
  作者：Wenqing Cai、Jingwei Wu、Wei Liu、Yafei Xie、Yuqiang Liu、Shuo Zhang、Weiren Xu、Lida Tang、Jianwu Wang、Guilong Zhao

  DOI：10.3390/molecules23020252

  日期：——

  In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a–1x and 1ha–1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly

  为了系统地探索和更好地理解二芳基甲烷骨架在设计强效尿酸转运蛋白 1 (URAT1) 抑制剂时的构效关系 (SAR)，设计并合成了 33 种化合物（1a-1x 和 1ha-1hi），并测定了它们的体外 URAT1 抑制活性 (IC50)。三轮系统的 SAR 探索导致发现了一种高效的新型 URAT1 抑制剂，1h，其效力分别比母体 lesinurad 和苯溴马隆强 200 倍和 8 倍（IC50 = 0.035 μM 对人 URAT1 1 小时 vs lesinurad 和苯溴马隆分别为 7.18 μM 和 0.28 μM）。化合物 1h 是迄今为止我们实验室发现的最有效的 URAT1 抑制剂，也可与目前正在临床试验中开发的最有效的抑制剂相媲美。
• Narrow SAR in odorant sensing Orco receptor agonists
  作者：Ian M. Romaine、Robert W. Taylor、Samsudeen P. Saidu、Kwangho Kim、Gary A. Sulikowski、Laurence J. Zwiebel、Alex G. Waterson

  DOI：10.1016/j.bmcl.2014.04.081

  日期：2014.6

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.