6-benzylidenamino-2-benzylthio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-one | 1337990-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-benzylidenamino-2-benzylthio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-one
• CAS: 1337990-67-6
• 化学式: C₄₄H₃₅N₃O₈S
• 分子量: 765.843
• InChiKey: HZEIZEIFHAYOAF-YLGJETLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  135.38
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  6-benzylidenamino-2-benzylthio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-one 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以53%的产率得到6-benzylidenamino-2-benzylthio-1-(β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-one
  参考文献：
  名称：

  Nucleosides 7⁹: Synthesis, Structure, and Biological Activity of New 6-Arylidenamino-2-Thio- and 2-BenzylthiopyrimidineN-Nucleosides

  摘要：

  The condensation of 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidine-4-one [compound (1)] with aromatic aldehydes (2) afforded azomethine derivatives (3). The formed azomethines underwent glycosidation with alpha-acetobromoglucose (4) to form the corresponding pyrimidine N-glycosides (6) and not S-glycosides (5). The interaction of (3) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-beta-D-ribofuranose (8) afforded the corresponding pyrimidine N-riboside (10) and not S-riboside (9). Deacetylation and debenzoylation of each of (6) and (10) by using Methanolic sodium methoxide afforded the corresponding free N-nucleosides (7) and (11), respectively. Next, the reaction of 2-benzylthio-6-benzylidenaminouracil (13) with (4) and (8) did not yield the corresponding protected N-nucleosides (14) and (17), whereas it afforded (15) and (18), respectively. The latter compounds (15) and (18) were stirred in methanolic sodium methoxide to yield the corresponding free N-nucleosides (16) and (19), respectively. The structures of products have been elucidated and reported and also some of the products were screened for their antimicrobial activity.

  DOI：

  10.1080/15257770.2011.597628
• 作为产物：
  描述：

  苯甲醛 在 硫酸氢铵 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 6-benzylidenamino-2-benzylthio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-one
  参考文献：
  名称：

  Nucleosides 7⁹: Synthesis, Structure, and Biological Activity of New 6-Arylidenamino-2-Thio- and 2-BenzylthiopyrimidineN-Nucleosides

  摘要：

  The condensation of 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidine-4-one [compound (1)] with aromatic aldehydes (2) afforded azomethine derivatives (3). The formed azomethines underwent glycosidation with alpha-acetobromoglucose (4) to form the corresponding pyrimidine N-glycosides (6) and not S-glycosides (5). The interaction of (3) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-beta-D-ribofuranose (8) afforded the corresponding pyrimidine N-riboside (10) and not S-riboside (9). Deacetylation and debenzoylation of each of (6) and (10) by using Methanolic sodium methoxide afforded the corresponding free N-nucleosides (7) and (11), respectively. Next, the reaction of 2-benzylthio-6-benzylidenaminouracil (13) with (4) and (8) did not yield the corresponding protected N-nucleosides (14) and (17), whereas it afforded (15) and (18), respectively. The latter compounds (15) and (18) were stirred in methanolic sodium methoxide to yield the corresponding free N-nucleosides (16) and (19), respectively. The structures of products have been elucidated and reported and also some of the products were screened for their antimicrobial activity.

  DOI：

  10.1080/15257770.2011.597628