156569-16-3Relevant articles and documents
Synthesis of 1-hydroxy-10-methyl-pyrimido [1,6-C][1,3]oxazine and the oxazepine derivative, structural mimicry of anti-constrained acyclic thymidine
Hsu, Ling-Yih,Wise, Dean S.,Drach, John C.,Townsend, Leroy B.
, p. 1481 - 1493 (1996)
A number of pyrimido[1,6-c][1,3]oxazine and -oxazepine derivatives, mimicry analogs of anti-constrained acyclic thymidine, have been prepared via treatment of lithiated 5,6-dimethyl-2,4-dimethoxypyrimidine with benzylchloromethyl ether or oxiran to furnish 2,4-dimethoxy-6-(1- benzyloxyethyl)-5-methylpyrimidine (2) and 2,4-dimethoxy-6-(1-hydroxypropyl)- 5-methylpyrimidine (8), respectively. Debenzylation of 2 afforded 2,4- dimethoxy-6-(1-hydroxyethyl)-5-methylpyrimidine (3). Chloromethylation of 3 and 8 with paraformaldehyde and gaseous hydrogen chloride produced reactive chloromethyl ether intermediates which were converted to the cyclized products 9-methyl-(1H, 2H, 4H, 7H)-pyrimido[1,6-c][1,3]-oxazine (5) and - oxazepine (9)-6,8-dione, respectively. By using selenium dioxide, allylic oxidation of 5 and 9 afforded the target compounds, a racemic mixture of (±)1-hydroxy-9-methyl-(1H, 2H, 4H, 7H)-pyrimido[1, 6-c][1,3]-oxazine (6) and -oxazepine (10)-6, 8-dione, respectively. Compounds 5, 6, 7, 9, and 10 were evaluated for activity against human immunodeficiency virus (HIV), herpes simplex virus type 1 (HSV-1) and human cytomegalovirus (HCMV). All of these compounds were inactive.
Synthesis of C-6 pyrimidine acyclic nucleoside analogs as potential antiviral agents
Hsu,Wise,Shannon,Drach,Townsend
, p. 563 - 584 (2007/10/02)
A number of pyrimidine acyclic nucleosides in which the acyclic moiety is attached to the C-6 position rather than N-1 of the pyrimidine ring have been prepared. This was accomplished via treatment of lithiated 2,4-dimethoxy- 5,6-dimethylpyrimidine, or, 2
