SYNTHESIS OF 2-O-ETHYL ANALOGS OF 3'-AZIDO-2',3'-DIDEOXYURIDINE AND 3'-FLUORO-2',3'-DIDEOXYURIDINES AND EVALUATION OF THEIR BIOLOGICAL-ACTIVITY AGAINST HIV

被引：5
作者：
ABDELBARY, HM
ABDELRAHMAN, AAH
PEDERSEN, EB
NIELSEN, C
机构：
[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE M,DENMARK
[2] STATENS SERUM INST,DEPT VIROL,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK
来源：
MONATSHEFTE FUR CHEMIE | 1995年 / 126卷 / 6-7期
关键词：
NUCLEOSIDES; CONVERGENT SYNTHESIS OF; URIDINES; 2-O-ETHYL; 2'; 3'-DIDEOXY-3'-FLUORO; AZT ANALOGS; HUMAN IMMUNODEFICIENCY VIRUS; HERPES SIMPLEX VIRUS;
D O I：
10.1007/BF00807175
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
2-O-Ethyluracil and 2-O-ethylthymine were silylated with 1,1,1,3,3,3-hexamethyldisilazane and condensed in the presence of TMS triflate with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside, 3-azido-2,3-dideoxy-D-erythro-pentofuranoside and 2,3-dideoxy-3-phthalimido-beta-D-erythro-pentofuranose furanose derivatives to give the corresponding 2-O-ethyl nucleosides. Deprotection with saturated methanolic ammonia afforded the 2',3'-dideoxy-3'-fluoro-2-O-ethyluridines whereas 3'-azido-2',3'-dideoxy-3-O-ethyluridine was obtained by deprotection with tetrabutylammonium fluoride in tetrahydrofuran. 3'-Amino-2',3'-dideoxy-3-O-ethyluridine could be obtained only by treatment of the corresponding 3'-azido nucleoside with triphenylphosphine in pyridine. 3'-Deoxy-2-O-ethyl-3'-fluorothymidine (6b) showed moderate activity against HIV-1.
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收藏
页码：811 / 817
页数：7
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