Synthesis and conformational analysis of pyrimidine nucleoside analogues with a rigid sugar moiety.
In order to obtain rigidity within the sugar moiety of nucleosides, some bicyclic pyrimidine nucleoside analogues were synthesized starting from cyclopentanone. The C-3' is fused to C-4' via a propylene linker in order to obtain a [3.3.0]-bicyclic ring system wherein the sugar moiety should be restricted to mainly the C-1'-exo conformation.
Björsne
M
M
Department of Organic Chemistry, Stockholm University, Sweden.
Szabó
T
T
Samuelsson
B
B
Classon
B
B
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002845:Chromatography; D003517:Cyclopentanes / Q000737:chemistry*; D003562:Cytidine / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects / Q000201:enzymology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011743:Pyrimidines / Q000737:chemistry*; D018894:Reverse Transcriptase Inhibitors / Q000494:pharmacology; D012984:Software; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D003517:Cyclopentanes; D011743:Pyrimidines; D018894:Reverse Transcriptase Inhibitors; D003562:Cytidine; C030986:pyrimidine