ethyl 2-(5-amino-1H-1,2,4-triazol-3-ylthio)acetate | 352349-53-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(5-amino-1H-1,2,4-triazol-3-ylthio)acetate
• 英文别名: 2-((5-amino-1H-1,2,4-triazol-3-yl)thio)ethyl acetate；ethyl 2-[(3-amino-1H-1,2,4-triazol-5-yl)sulfanyl]acetate；ethyl 2-[(5-amino-1H-1,2,4-triazol-3-yl)sulfanyl]acetate
• CAS: 352349-53-2
• 化学式: C₆H₁₀N₄O₂S
• mdl: MFCD08273691
• 分子量: 202.237
• InChiKey: HJEVFKIDKNFIQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(5-amino-1H-1,2,4-triazol-3-ylthio)acetate 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  [1,2,4]三唑并[1,5-a]嘧啶衍生物：结构-活性关系研究导致高选择性ENPP1抑制剂

  摘要：

  STING（干扰素基因刺激剂）途径是调节先天免疫的途径之一，细胞外水解酶外核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）已被确定为其显性负调节因子。由于激活先天免疫系统是治疗各种传染病和癌症的一种有前景的策略，ENPP1抑制剂作为候选药物引起了极大的关注。我们之前通过使用荧光探针TG-mAMP进行化学筛选，鉴定了具有[1,2,4]三唑并[1,5-]嘧啶支架的小分子ENPP1抑制剂。在这项研究中，我们详细评估了命中化合物和先导化合物的构效关系，并成功开发了不仅能强烈、选择性地抑制 ENPP1 的化合物，而且还能在细胞系统中抑制 ENPP1。

  DOI：

  10.1016/j.bmcl.2024.129820
• 作为产物：
  描述：

  溴乙酸乙酯 、 3-amino-1H-1,2,4-triazole-5-thiol 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 ethyl 2-(5-amino-1H-1,2,4-triazol-3-ylthio)acetate
  参考文献：
  名称：

  [1,2,4]三唑并[1,5-a]嘧啶衍生物：结构-活性关系研究导致高选择性ENPP1抑制剂

  摘要：

  STING（干扰素基因刺激剂）途径是调节先天免疫的途径之一，细胞外水解酶外核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）已被确定为其显性负调节因子。由于激活先天免疫系统是治疗各种传染病和癌症的一种有前景的策略，ENPP1抑制剂作为候选药物引起了极大的关注。我们之前通过使用荧光探针TG-mAMP进行化学筛选，鉴定了具有[1,2,4]三唑并[1,5-]嘧啶支架的小分子ENPP1抑制剂。在这项研究中，我们详细评估了命中化合物和先导化合物的构效关系，并成功开发了不仅能强烈、选择性地抑制 ENPP1 的化合物，而且还能在细胞系统中抑制 ENPP1。

  DOI：

  10.1016/j.bmcl.2024.129820

文献信息

• [EN] 2,3-DIHYDROBENZOFURAN-5-YL COMPOUNDS AS DYRK KINASE INHIBITORS<br/>[FR] COMPOSÉS 2,3-DIHYDROBENZOFURAN-5-YL UTILISÉS COMME INHIBITEURS DE KINASES DYRK
  申请人：4SC DISCOVERY GMBH

  公开号：WO2014202638A9

  公开（公告）日：2016-03-03
• Synthesis and Evaluation of 1,2,4-Triazolo[1,5-<i>a</i>]pyrimidines as Antibacterial Agents Against <i>Enterococcus faecium</i>
  作者：Huan Wang、Mijoon Lee、Zhihong Peng、Blas Blázquez、Elena Lastochkin、Malika Kumarasiri、Renee Bouley、Mayland Chang、Shahriar Mobashery

  DOI：10.1021/jm501831g

  日期：2015.5.28

  Rapid emergence of antibiotic resistance is one of the, most Challenging global public health concerns. In particular; vancomycin-resistant Enterococcus faecium infections have been increasing in frequency, representing 25% of enterococci infections in intensive care units. A novel class of 1,2,4-triazolo[1,5-a]pyrimidines active against E. faecium is reported herein We used a three component Biginelli-like heterocyclization reaction for the synthesis of a series of these derivatives based on reactions of aldehydes, beta-dicarbonyl compounds, and 3-alkylthio-5-amino-1,2,4-triazoles. The resulting compounds were assayed for,antimicrobial activity against the ESKAPE panel of bacteria, followed by investigation of their in vitro activities. These analyses identified :a subset of 1,2,4-triazolo[1,5-a]pyrimidines that had good narrow spectrum antibacterial activity against E faecium and exhibited metabolic stability with low intrinsic clearance. Macromolecular synthesis assays revealed cell-wall biosynthesis as the target of these antibiotics.
• Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives
  作者：Qiong Chen、Xiao-Lei Zhu、Li-Li Jiang、Zu-Ming Liu、Guang-Fu Yang

  DOI：10.1016/j.ejmech.2007.04.021

  日期：2008.3

  In order to search novel agrochemicals with higher antifungal activity, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives bearing 1,3,4-oxadiazole moieties were designed and synthesized. Their antifungal activities against Rhizoctonia solani were evaluated in vitro. By determining the EC50 values of all the newly synthesized compounds and 10 formerly synthesized compounds, compound 8r, 2-((5-(sec-butylthio)1,3,4-oxadiazol-2-yl)-methylthio)-5-dimethyl-1,2,4-triazolo-[1,5-a]pyrimidine, was found to display the highest antifungal activity (EC50 = 6.57 mu g mL(-1)). Based on the quantitative structure-activity relationships analyses, 2-(1-(5-(sec-butylthio)- 1,3,4-oxadiazol-2-yl)ethylthio)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (9j) was designed and synthesized, which was found to display much higher activity (EC50 = 3.34 mu g mL(-1)) than compound 8r and the control. To further explore the comprehensive structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed and a statistically reliable model with good predictive power (r(2) = 0.929, q(2) = 0.588) was achieved on the basis of the common substructure-based alignment. According to the CoMFA model, the structure-antifungal activity relationship was explained reasonably. (c) 2007 Elsevier Masson SAS. All rights reserved.