N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines: Synthesis and structural study (CROSBI ID 193283)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Meščić, Andrijana ; Glavač, Danijel ; Osmanović, Amar ; Završnik, Davorka ; Cetina, Mario ; Makuc, Damjan ; Plavec, Janez ; Ametamey, Simon M. ; Raić-Malić, Silvana
engleski
N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines: Synthesis and structural study
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.
N-acyclic and O-acyclic pyrimidine nucleoside analogs ; NMR ; regioisomers ; self-assembling ; X-ray diffraction
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Podaci o izdanju
1039
2013.
160-166
objavljeno
0022-2860
1872-8014
10.1016/j.molstruc.2013.02.010