Synthesis of 2'- or 3'-O-heteroaryl substituted nucleic acid derivatives and their biological properties.
The successful preparation of 3'-O-heteroaryl substituted thymidine derivatives were developed by the reaction of 5'-O-(tert-butyldimethylsilyl)thymidine with heteroaromatic halides in the presence of sodium hydride. In a similar manner, 2' or 3'-O-heteroaryl substituted uridine derivatives were obtained by the use of 5'-O-(tert-butyldimethylsilyl)uridine. All the arylations proceeded selectively at the site of the hydroxyl group and reactions of heteroaromatic halides with the nucleobase residues were not observed. Desilylation of the nucleic acid derivatives synthesized afforded 2'- or 3'-O-heteroaryl substituted thymidine or uridine derivatives in good yields. The anti-BVDV assay of the synthesized 2'- or 3'-O-heteroarylsubstituted thymidine and uridine derivatives were studied.
Taguchi
Haruhiko
H
Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Narita
Takeshi
T
Seio
Kohji
K
Sekine
Mitsuo
M
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis; D013936:Thymidine / Q000737:chemistry*; D014529:Uridine / Q000737:chemistry*
D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides; D013936:Thymidine; D014529:Uridine