Author/Authors :
Me??i?، نويسنده , , Andrijana and Glava?، نويسنده , , Danijel and Osmanovi?، نويسنده , , Amar and Zavr?nik، نويسنده , , Davorka and Cetina، نويسنده , , Mario and Makuc، نويسنده , , Damjan and Plavec، نويسنده , , Janez and Ametamey، نويسنده , , Simon M. and Rai?-Mali?، نويسنده , , Silvana، نويسنده ,
Abstract :
Synthesis of novel 5-(2-hydroxyethyl) and 5-(3-hydroxypropyl) acyclic pyrimidine nucleosides is described. Introduction of penciclovir-like side chain in C-5 substituted pyrimidines occurred both at N-1 and O-2 position of pyrimidine moiety that was corroborated by correlation of signals in 2D HMBC spectra. Therefore, alkylation of 5-(acetoxyethyl)-4-methoxypyrimidin-2-one (2a) and 5-(acetoxypropyl)-4-methoxypyrimidin-2-one (2b) afforded mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 49: 45 (4a: 5a) and 41: 21 (4b: 5b). Structures of 5-(acetoxyalkyl)-4-methoxypyrimidin-2-ones, as the first examples of 4-methoxypyrimidin-2-ones, were unambiguously confirmed by single crystal X-ray diffraction analysis.
Keywords :
N-acyclic and O-acyclic pyrimidine nucleoside analogs , Regioisomers , X-ray diffraction , NMR , Self-assembling
