6-acetyl-3-amino-5-methyl-2-sulfanylidene-1H-thieno[2,3-d]pyrimidin-4-one | 1224375-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 6-acetyl-3-amino-5-methyl-2-sulfanylidene-1H-thieno[2,3-d]pyrimidin-4-one
• CAS: 1224375-08-9
• 化学式: C₉H₉N₃O₂S₂
• 分子量: 255.321
• InChiKey: ZRNAONCDUKEEKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetyl-3-amino-5-methyl-2-sulfanylidene-1H-thieno[2,3-d]pyrimidin-4-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以78%的产率得到3-amino-6-acetyl-5-methyl-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-thio)-thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

  摘要：

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.056
• 作为产物：
  描述：

  Ethyl 5-acetyl-4-methyl-2-(methylsulfanylcarbothioylamino)thiophene-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以85%的产率得到6-acetyl-3-amino-5-methyl-2-sulfanylidene-1H-thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

  摘要：

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.056