[5-cyano-2-methyl-4-(5-methylfuran-2-yl)-6-thioxo-1,6-dihydropyridine-3]-[N-(2-methoxyphenyl)]carboxamide | 406723-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [5-cyano-2-methyl-4-(5-methylfuran-2-yl)-6-thioxo-1,6-dihydropyridine-3]-[N-(2-methoxyphenyl)]carboxamide
• 英文别名: 5-cyano-N-(2-methoxyphenyl)-2-methyl-4-(5-methylfuran-2-yl)-6-sulfanylidene-1H-pyridine-3-carboxamide
• CAS: 406723-43-1
• 化学式: C₂₀H₁₇N₃O₃S
• 分子量: 379.439
• InChiKey: WZRAWISBZYLDSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [5-cyano-2-methyl-4-(5-methylfuran-2-yl)-6-thioxo-1,6-dihydropyridine-3]-[N-(2-methoxyphenyl)]carboxamide 、 氯乙酸苄酯 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以67%的产率得到[3-Cyano-5-(2-methoxy-phenylcarbamoyl)-6-methyl-4-(5-methyl-furan-2-yl)-pyridin-2-ylsulfanyl]-acetic acid benzyl ester
  参考文献：
  名称：

  New approach to the synthesis of substituted 5-arylcarbamoyl-3-cyano-6-methylpyridine-2(1h)-thiones. Molecular and crystal structure of 2-allylthio-3-cyano-5-(2-methoxyphenylcarbamoyl)-6-methyl-4-(5-methyl-2-furyl)-1,4-dihydropyridine

  摘要：

  DOI：

  10.1007/s10593-006-0045-y
• 作为产物：
  描述：

  5-Cyano-6-mercapto-2-methyl-4-(5-methyl-furan-2-yl)-1,4-dihydro-pyridine-3-carboxylic acid (2-methoxy-phenyl)-amide; compound with morpholine 在 溶剂黄146 作用下， 以68%的产率得到[5-cyano-2-methyl-4-(5-methylfuran-2-yl)-6-thioxo-1,6-dihydropyridine-3]-[N-(2-methoxyphenyl)]carboxamide
  参考文献：
  名称：

  New approach to the synthesis of substituted 5-arylcarbamoyl-3-cyano-6-methylpyridine-2(1h)-thiones. Molecular and crystal structure of 2-allylthio-3-cyano-5-(2-methoxyphenylcarbamoyl)-6-methyl-4-(5-methyl-2-furyl)-1,4-dihydropyridine

  摘要：

  DOI：

  10.1007/s10593-006-0045-y

文献信息

• Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates
  作者：V. V. Dotsenko、I. A. Lebedeva、S. G. Krivokolysko、M. V. Povstyanoi、V. M. Povstyanoi、E. O. Kostyrko

  DOI：10.1007/s10593-012-1016-0

  日期：2012.6

  Alkylation of N-methylmorpholinium 4-Ar-1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar-1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar-1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.
• New approach to the synthesis of substituted 5-arylcarbamoyl-3-cyano-6-methylpyridine-2(1h)-thiones. Molecular and crystal structure of 2-allylthio-3-cyano-5-(2-methoxyphenylcarbamoyl)-6-methyl-4-(5-methyl-2-furyl)-1,4-dihydropyridine
  作者：V. D. Dyachenko、A. N. Chernega

  DOI：10.1007/s10593-006-0045-y

  日期：2006.1