2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide | 95877-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide
• 英文别名: 2-Propenethioamide, 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-
• CAS: 95877-09-1
• 化学式: C₁₁H₁₀N₂O₂S
• 分子量: 234.279
• InChiKey: QUNKDXWFLCLTPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide 在 哌啶 、 氢氧化钾 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-acetyl-3-cyano-4-(4-hydroxy-3-methoxy-phenyl)-6-phenyl-pyridin-2-ylsulfanyl]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of thiopyridines and their hydrogenated thioglycosides via piperidinium salts

  摘要：

  The synthesis of several new thiopyridines and their hydrogenated thioglycosides via the reaction of piperidinium salts of dihydropyridinethiones with alpha-halogeno sugars is described. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01242-x
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 香草醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide
  参考文献：
  名称：

  新型杂环氰硫基乙酰胺衍生物的合成及镇痛活性

  摘要：

  摘要 氰基硫代乙酰胺与芳族醛和1,3-二羰基化合物反应，然后进行氨甲基化或S-烷基化反应，得到一系列带有1,2,3,4-四氢吡啶或1,4,5,6,7,8的杂环衍生物-六氢喹啉片段。测试了所得化合物在体内的镇痛作用。在动力学上，一些制备的化合物显示出比酮咯酸更好的抗伤害感受作用。

  DOI：

  10.1134/s107036322102002x

文献信息

• Multicomponent Synthesis and Molecular and Crystal Structure of New Derivatives of Partially Hydrogenated Quinolines
  作者：I. V. Dyachenko、V. D. Dyachenko、P. V. Dorovatovskii、V. N. Khrustalev、V. G. Nenaidenko

  DOI：10.1134/s1070428021110038

  日期：2021.11

  condensation of aromatic aldehydes, cyanothioacetamide, 1-(cyclohex-1-en-1-yl)azepine, and α-halocarbonyl compounds was studied. As a result, new derivatives of partially hydrogenated quinolines were synthesized. The molecular and crystal structures of a number of the synthesized heterocycles were studied X-ray analysis.

  摘要 研究了芳香醛、氰硫代乙酰胺、1-(环己-1-烯-1-基)氮杂和α-卤代羰基化合物的多组分缩合。结果，合成了部分氢化喹啉的新衍生物。通过X射线分析研究了许多合成杂环的分子和晶体结构。
• 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.