N5-2-丙烯-1-基-1,2,4-噻二唑-3,5-二胺 | 60093-16-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N5-2-丙烯-1-基-1,2,4-噻二唑-3,5-二胺
• 英文名称: 3-amino-5-allylamino-1,2,4-thiadiazole
• 英文别名: N⁵-allyl-[1,2,4]thiadiazole-3,5-diamine；5-N-prop-2-enyl-1,2,4-thiadiazole-3,5-diamine
• CAS: 60093-16-5
• 化学式: C₅H₈N₄S
• 分子量: 156.211
• InChiKey: MYISXCAAYLVJSC-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N5-2-丙烯-1-基-1,2,4-噻二唑-3,5-二胺 、 4-碘异硫氰酸苯酯 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
  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
• 作为产物：
  描述：

  1-烯丙基-3-氰基硫脲钠盐 在 sodium hydroxide 、 氨 、 氯 作用下， 生成 N5-2-丙烯-1-基-1,2,4-噻二唑-3,5-二胺
  参考文献：
  名称：

  离子交换联苯胺-I：环烷基磺酸联胺钾-烷基-氰基亚氨基二硫代碳酸酯

  摘要：

  烷基烷基氰基氨基二硫代碳酸钾1与α-CH-酸卤代化合物反应成4-氨基噻唑3，一氯胺反应生成3-氨基-1,2,4-噻二唑5，与α-卤代羧酸酐反应成4-噻唑烷酮描述了导数12。讨论了合成化合物的质谱和红外光谱特征。

  DOI：

  10.1016/s0040-4020(01)93783-4

文献信息

• WALEK W.; PALLAS M.; AUGUSTIN M., TETRAHEDRON <TETR-AB>, 1976, 32, NO 5, 623-627
  作者：WALEK W.、 PALLAS M.、 AUGUSTIN M.

  DOI：——

  日期：——
• Beiträge zum reaktionsverhalten von derivaten der imidodithiokohlensäure—I
  作者：W. Walek、M. Pallas、M. Augustin

  DOI：10.1016/s0040-4020(01)93783-4

  日期：1976.1

  The reaction of potassium-alkyl-cyanoimidodithiocarbonate 1 with α-CH-acid halo compounds to 4-aminothiazoles 3, with monochloramine to 3-amino-1,2,4-thiadiazoles 5, and with α-halocarboxylic acid anilides to 4-thiazolidinones derivatives 12 is described. Characteristics of mass- and IR-spectra of the synthesized compounds are discussed.

  烷基烷基氰基氨基二硫代碳酸钾1与α-CH-酸卤代化合物反应成4-氨基噻唑3，一氯胺反应生成3-氨基-1,2,4-噻二唑5，与α-卤代羧酸酐反应成4-噻唑烷酮描述了导数12。讨论了合成化合物的质谱和红外光谱特征。
• 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.