3-(prop-2-en-1-ylsulfanyl)-1,2,4-thiadiazol-5-amine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(prop-2-en-1-ylsulfanyl)-1,2,4-thiadiazol-5-amine
• 英文别名: 3-allylthio-5-amino-1,2,4-thiadiazole；3-Allylsulfanyl-[1,2,4]thiadiazol-5-ylamine；3-prop-2-enylsulfanyl-1,2,4-thiadiazol-5-amine
• 化学式: C₅H₇N₃S₂
• 分子量: 173.263
• InChiKey: GMVKUQPLPVHBOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘异硫氰酸苯酯 、 3-(prop-2-en-1-ylsulfanyl)-1,2,4-thiadiazol-5-amine 在 N-甲基吗啉 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 1-(4-Iodophenyl)-3-(3-prop-2-enylsulfanyl-1,2,4-thiadiazol-5-yl)thiourea
  参考文献：
  名称：

  Optimization of 1,3-disubstituted urea-based inhibitors of Zika virus infection

  摘要：

  Zika virus (ZIKV) has become a public health concern worldwide due to its association with congenital abnormalities and neurological diseases. To date, no effective vaccines or antiviral drugs have been approved for the treatment of ZIKV infection, and new inexpensive therapeutic options are urgently needed. In this study, we have used an in vitro plaque assay to assess an antiviral activity of the second generation of anti-ZIKV compounds, based on 1,3-disubstituted (thio)urea scaffold. Several compounds in the library were found to possess excellent activity against Zika virus with IC50 values < 200 pM. The most active analog, A5 exhibited an exceptional IC50 = 85.1 +/- 1.7 pM. Further analysis delineated structural requirements necessary for potent antiviral effects of this class of compounds. Collectively, our findings suggest that 1,3-disubstituted (thio)urea derivatives are excellent preclinical candidates for the development of anti-ZIKV therapeutics.

  DOI：

  10.1016/j.bmcl.2019.126626

文献信息

• [EN] COMPOUNDS FOR TREATING OR PREVENTING FLAVIVIRUS INFECTIONS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT OU LA PRÉVENTION D'INFECTIONS À FLAVIVIRUS
  申请人：UNIV CALIFORNIA

  公开号：WO2019070709A8

  公开（公告）日：2019-09-06
• Optimization of 1,3-disubstituted urea-based inhibitors of Zika virus infection
  作者：Ronik Khachatoorian、Ewa D. Micewicz、Alina Micewicz、Samuel W. French、Piotr Ruchala

  DOI：10.1016/j.bmcl.2019.126626

  日期：2019.10

  Zika virus (ZIKV) has become a public health concern worldwide due to its association with congenital abnormalities and neurological diseases. To date, no effective vaccines or antiviral drugs have been approved for the treatment of ZIKV infection, and new inexpensive therapeutic options are urgently needed. In this study, we have used an in vitro plaque assay to assess an antiviral activity of the second generation of anti-ZIKV compounds, based on 1,3-disubstituted (thio)urea scaffold. Several compounds in the library were found to possess excellent activity against Zika virus with IC50 values < 200 pM. The most active analog, A5 exhibited an exceptional IC50 = 85.1 +/- 1.7 pM. Further analysis delineated structural requirements necessary for potent antiviral effects of this class of compounds. Collectively, our findings suggest that 1,3-disubstituted (thio)urea derivatives are excellent preclinical candidates for the development of anti-ZIKV therapeutics.