4-furan-2-ylmethyl-5-methyl-4H-[1,2,4]triazole-3-thiol

• 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-furan-2-ylmethyl-5-methyl-4H-[1,2,4]triazole-3-thiol
• 英文别名: 4-(furan-2-ylmethyl)-3-methyl-1H-1,2,4-triazole-5-thione
• 化学式: C₈H₉N₃OS
• 分子量: 195.245
• InChiKey: QBTCDHQRVRTWIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-furan-2-ylmethyl-5-methyl-4H-[1,2,4]triazole-3-thiol 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.34h， 生成 N-(4-chlorophenyl)-2-{[4-(2-furylmethyl)-5-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}acetamide
  参考文献：
  名称：

  Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace

  摘要：

  Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).

  DOI：

  10.1016/j.bmc.2019.115142
• 作为产物：
  描述：

  异硫氢酸糠酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-furan-2-ylmethyl-5-methyl-4H-[1,2,4]triazole-3-thiol
  参考文献：
  名称：

  Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace

  摘要：

  Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).

  DOI：

  10.1016/j.bmc.2019.115142

文献信息

• VERWENDUNG VON SUBSTITUIERTEN THIO-1,2,4-TRIAZOLEN ZUR STEIGERUNG DER STRESSTOLERANZ IN PFLANZEN
  申请人：Bayer CropScience AG

  公开号：EP3210469A1

  公开（公告）日：2017-08-30

  Die Erfindung betrifft die Verwendung substituierter Thio-1,2,4-triazole oder deren Salze wobei die Reste und Indizes in der allgemeinen Formel (I) den in der Beschreibung gegebenen Definitionen entsprechen, zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress und/oder zur Erhöhung des Pflanzenertrags.

  本发明涉及取代的硫代-1,2,4-三唑或其盐类的用途 其中通式（I）中的基团和指数与描述中给出的定义相对应、 用于提高植物对非生物胁迫的耐受性和/或增加植物产量。
• Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2–S100A10 protein interaction
  作者：Tummala R.K. Reddy、Chan Li、Xiaoxia Guo、Peter M. Fischer、Lodewijk V. Dekker

  DOI：10.1016/j.bmc.2014.07.043

  日期：2014.10

  Recent target validation studies have shown that inhibition of the protein interaction between annexin A2 and the S100A10 protein may have potential therapeutic benefits in cancer. Virtual screening identified certain 3,4,5-trisubstituted 4H-1,2,4-triazoles as moderately potent inhibitors of this interaction. A series of analogues were synthesized based on the 1,2,4-triazole scaffold and were evaluated for inhibition of the annexin A2-S100A10 protein interaction in competitive binding assays. 2-[(5-[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]methyl}-4-(furan-2-ylmethyl)-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[4-(propan-2-yl)phenyl]acetamide (36) showed improved potency and was shown to disrupt the native complex between annexin A2 and S100A10.