Mosselhi Mosselhi A N, Break Laila M
Department of Chemistry, Faculty of Science, Taif University, Taif, Saudi Arabia.
Nucleosides Nucleotides Nucleic Acids. 2011 Sep;30(9):681-95. doi: 10.1080/15257770.2011.597628.
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 α-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-β-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. Graphical Abstract:
6-氨基-2-硫代-2,3-二氢-1H-嘧啶-4-酮[化合物(1)]与芳香醛(2)缩合得到偶氮甲碱衍生物(3)。生成的偶氮甲碱与α-乙酰溴葡萄糖(4)进行糖苷化反应，形成相应的嘧啶N-糖苷(6)，而非S-糖苷(5)。(3)与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖(8)相互作用，得到相应的嘧啶N-核糖苷(10)，而非S-核糖苷(9)。分别用甲醇钠对(6)和(10)进行脱乙酰化和脱苯甲酰化反应，分别得到相应的游离N-核苷(7)和(11)。接下来，2-苄硫基-6-苄叉氨基尿嘧啶(13)与(4)和(8)反应，未得到相应的保护N-核苷(14)和(17)，而是分别得到了(15)和(18)。将后两种化合物(15)和(18)在甲醇钠中搅拌，分别得到相应的游离N-核苷(16)和(19)。已对产物的结构进行了阐明和报道，并且还对部分产物的抗菌活性进行了筛选。图形摘要：
