6-(2-Furyl)-1,3,5-thiadiazine-2,4-dione | 80784-85-6

• 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: 6-(2-Furyl)-1,3,5-thiadiazine-2,4-dione
• 英文别名: 6-(furan-2-yl)-1,3,5-thiadiazine-2,4-dione
• CAS: 80784-85-6
• 化学式: C₇H₄N₂O₃S
• 分子量: 196.186
• InChiKey: QBLTVSLHHZFXGR-UHFFFAOYSA-N

物化性质

• 熔点：
  212-215 °C (decomp)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呋喃-2-硫代甲酰胺 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 6-(2-Furyl)-1,3,5-thiadiazine-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activity of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones

  摘要：

  A series of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones (1a-m) was prepared by treatment of alkyl, aryl, and heterocyclic primary thioamides with phenoxycarbonyl isocyanate to give N-(phenoxycarbonyl)-N'-thioacylureas, which gave 1 upon heating in refluxing xylene solution or upon treatment with aqueous sodium carbonate solution followed by acidification. 1H NMR and infrared spectral evidence indicates that the 6-alkyl derivatives 1a,b,l,m exist predominately in the exocyclic alkylidene tautomeric form. The major product obtained from alkaline and acid hydrolysis of the 6-phenyl derivative 1c was found to be benzoic acid and benzoylurea, respectively. The majority of compounds 1a-m exhibited in vitro antifungal activity against Candida albicans and Trichophyton mentagrophytes. Several derivatives, 1b-d,h,j, displayed minimum inhibitory concentration values below 2 micrograms/mL against Trichophyton mentagrophytes. Four derivatives, 1c,e,g,h, inhibited the growth of Seratia marcesens, Staphylococcus aureus, and Staphylococcus epidermis in an in vitro sensitivity disk assay. 2-Furyl derivative 1h displayed antileukemic activity against P-388 lymphocytic leukemia.

  DOI：

  10.1021/jm00346a028

文献信息

• COBURN, R. A.;HO, CHEUN-HUEI;BRONSTEIN, M. L., J. MED. CHEM., 1982, 25, N 4, 481-483
  作者：COBURN, R. A.、HO, CHEUN-HUEI、BRONSTEIN, M. L.

  DOI：——

  日期：——
• Synthesis and in vitro antimicrobial activity of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones
  作者：Robert A. Coburn、Chuen Huei Ho、Martha L. Bronstein

  DOI：10.1021/jm00346a028

  日期：1982.4

  A series of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones (1a-m) was prepared by treatment of alkyl, aryl, and heterocyclic primary thioamides with phenoxycarbonyl isocyanate to give N-(phenoxycarbonyl)-N'-thioacylureas, which gave 1 upon heating in refluxing xylene solution or upon treatment with aqueous sodium carbonate solution followed by acidification. 1H NMR and infrared spectral evidence indicates that the 6-alkyl derivatives 1a,b,l,m exist predominately in the exocyclic alkylidene tautomeric form. The major product obtained from alkaline and acid hydrolysis of the 6-phenyl derivative 1c was found to be benzoic acid and benzoylurea, respectively. The majority of compounds 1a-m exhibited in vitro antifungal activity against Candida albicans and Trichophyton mentagrophytes. Several derivatives, 1b-d,h,j, displayed minimum inhibitory concentration values below 2 micrograms/mL against Trichophyton mentagrophytes. Four derivatives, 1c,e,g,h, inhibited the growth of Seratia marcesens, Staphylococcus aureus, and Staphylococcus epidermis in an in vitro sensitivity disk assay. 2-Furyl derivative 1h displayed antileukemic activity against P-388 lymphocytic leukemia.