N-1,3-benzothiazol-2-yl-5-cyano-4-(2-furyl)-6-({2-[(4-isopropylphenyl)-amino]-2-oxoethyl}thio)-2-methyl-1,4-dihydropyridine-3-carboxamide | 896094-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-1,3-benzothiazol-2-yl-5-cyano-4-(2-furyl)-6-({2-[(4-isopropylphenyl)-amino]-2-oxoethyl}thio)-2-methyl-1,4-dihydropyridine-3-carboxamide
• 英文别名: N-(1,3-benzothiazol-2-yl)-5-cyano-4-(furan-2-yl)-2-methyl-6-[(2-oxo-2-{[4-(propan-2-yl)phenyl]amino}ethyl)sulfanyl]-1,4-dihydropyridine-3-carboxamide；N-(1,3-benzothiazol-2-yl)-5-cyano-4-(furan-2-yl)-2-methyl-6-[2-oxo-2-(4-propan-2-ylanilino)ethyl]sulfanyl-1,4-dihydropyridine-3-carboxamide
• CAS: 896094-42-1
• 化学式: C₃₀H₂₇N₅O₃S₂
• 分子量: 569.708
• InChiKey: SKHWGUSXPKRQEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  174
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-furfurylidenecyanothioacetamide 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 N-1,3-benzothiazol-2-yl-5-cyano-4-(2-furyl)-6-({2-[(4-isopropylphenyl)-amino]-2-oxoethyl}thio)-2-methyl-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  Inhibitors of Tick-Borne Flavivirus Reproduction from Structure-Based Virtual Screening

  摘要：

  Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]-thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK. cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.

  DOI：

  10.1021/ml400226s

文献信息

• Inhibitors of Tick-Borne Flavivirus Reproduction from Structure-Based Virtual Screening
  作者：Dmitry I. Osolodkin、Liubov I. Kozlovskaya、Evgenia V. Dueva、Victor V. Dotsenko、Yulia V. Rogova、Konstantin A. Frolov、Sergey G. Krivokolysko、Ekaterina G. Romanova、Alexey S. Morozov、Galina G. Karganova、Vladimir A. Palyulin、Vladimir M. Pentkovski、Nikolay S. Zefirov

  DOI：10.1021/ml400226s

  日期：2013.9.12

  Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]-thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK. cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.