2-cyano-3-(5-methylfur-2-yl)prop-2-enethioamide | 68029-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-cyano-3-(5-methylfur-2-yl)prop-2-enethioamide
• 英文别名: 5-Methyl-2-furfurylidenecyanothioacetamide；2-cyano-3-(5-methylfuran-2-yl)prop-2-enethioamide
• CAS: 68029-50-5
• 化学式: C₉H₈N₂OS
• mdl: MFCD01049133
• 分子量: 192.241
• InChiKey: OKWGPYJKVYQHAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(5-methylfur-2-yl)prop-2-enethioamide 以 乙醇 为溶剂， 反应 74.0h， 生成 5-acetyl-6-methyl-4-(5-methylfuran-2-yl)-2-(prop-2-yn-1-ylthio)nicotinonitrile
  参考文献：
  名称：

  官能化腈和6-烷基硫烷基-1,4-二氢烟酸酯的新多组分合成

  摘要：

  摘要丙二腈，硫化氢，芳基或杂芳基醛，1,3-二羰基化合物和烷基化试剂的多组分缩合可提供官能化的腈和6-烷基硫烷基-1,4-二氢烟酸的酯，它们的芳香族类似物和1,4-二氢噻吩并[ 2,3- b ]吡啶。

  DOI：

  10.1134/s1070363220030068
• 作为产物：
  描述：

  5-甲基呋喃醛 、 2-氰基硫代乙酰胺 以 乙醇 为溶剂， 反应 0.5h， 生成 2-cyano-3-(5-methylfur-2-yl)prop-2-enethioamide
  参考文献：
  名称：

  官能化腈和6-烷基硫烷基-1,4-二氢烟酸酯的新多组分合成

  摘要：

  摘要丙二腈，硫化氢，芳基或杂芳基醛，1,3-二羰基化合物和烷基化试剂的多组分缩合可提供官能化的腈和6-烷基硫烷基-1,4-二氢烟酸的酯，它们的芳香族类似物和1,4-二氢噻吩并[ 2,3- b ]吡啶。

  DOI：

  10.1134/s1070363220030068

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.
• Design and Synthesis of Pyrido[2,1-<i>b</i>][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction
  作者：Victor V. Dotsenko、Konstantin A. Frolov、Tatyana M. Pekhtereva、Olena S. Papaianina、Sergey Yu. Suykov、Sergey G. Krivokolysko

  DOI：10.1021/co5000807

  日期：2014.10.13

  This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.
• Multicomponent Syntheses of Cycloalka[b]pyridines and Chromenes
  作者：I. V. Dyachenko、V. D. Dyachenko、P. V. Dorovatovskii、V. N. Khrustalev、V. G. Nenajdenko

  DOI：10.1134/s1070428023070060

  日期：2023.7
• (2E,2′E)-2,2′-(1,2,4-Thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]: Synthesis and Antidote Activity Towards 2,4-D Herbicide
  作者：P. G. Dakhno、V. V. Dotsenko、V. D. Strelkov、V. K. Vasilin、N. A. Aksenov、I. V. Aksenova

  DOI：10.1134/s1070363222120337

  日期：2022.12
• New Multicomponent Synthesis of Functionalized Nitriles and Esters of 6-Alkylsulfanyl-1,4-dihydronicotinic Acids
  作者：I. N. Kalashnik、V. D. Dyachenko

  DOI：10.1134/s1070363220030068

  日期：2020.3

  AbstractThe multicomponent condensation of malononitrile, hydrogen sulfide, aryl or hetaryl aldehydes, 1,3-dicarbonyl compounds and alkylating reagents afforded functionalized nitriles and esters of 6-alkylsulfanyl-1,4-dihydronicotinic acids, their aromatic analogues and 1,4-dihydrothieno[2,3-b]pyridines.

  摘要丙二腈，硫化氢，芳基或杂芳基醛，1,3-二羰基化合物和烷基化试剂的多组分缩合可提供官能化的腈和6-烷基硫烷基-1,4-二氢烟酸的酯，它们的芳香族类似物和1,4-二氢噻吩并[ 2,3- b ]吡啶。