6-benzylidenamino-1(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one | 1337990-66-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 6-benzylidenamino-1(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• CAS: 1337990-66-5
• 化学式: C₃₇H₂₉N₃O₈S
• 分子量: 675.719
• InChiKey: FHXWXNUKZLPRRR-LXSYHGDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138.28
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-benzylidenamino-1(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以40%的产率得到6-benzylidenamino-1-(β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-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：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 以70%的产率得到6-benzylidenamino-1(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-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