SYNTHESIS OF 3'-ALKYLTHIO-2',3'-DIDEOXY NUCLEOSIDES WITH POTENTIAL ANTI-HIV ACTIVITY FROM 2-DEOXY-D-RIBOSE, USING A PHOSPHORUS PENTOXIDE REAGENT

被引：4
|
作者：
DUEHOLM, KL
MOTAWIA, MS
PEDERSEN, EB
NIELSEN, C
LUNDT, I
机构：
[1] STATENS SERUM INST,DEPT VIROL,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK
[2] TECH UNIV DENMARK,DEPT ORGAN CHEM,DK-2800 LYNGBY,DENMARK
来源：
ARCHIV DER PHARMAZIE | 1992年 / 325卷 / 09期
关键词：
D O I：
10.1002/ardp.19923250914
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Direct condensation of 2-deoxy-D-ribose (1) with mercaptans using the P4O10/H2O/Bu3N reagent in chloroform resulted in coupling at C-3 to give the anomeric mixtures of the corresponding pentopyranoses 2 and pentofuranoses 3. After acetylation with acetic anhydride in dry pyridine of these 3-alkylthio pentofuranoses, coupling with the nucleobases uracil, thymine, and cytosine in accordance with the Friedel-Crafts catalyzed silyl Hilbert-Johnson method yielded the acetylated D-erythro nucleosides 7 as anomeric mixtures, separable only by means of chromatography either before or after deprotection with ammonia. The nucleosides 8a-e were devoid of any activity against HSV-1 and HIV-1.
引用
收藏
页码：597 / 601
页数：5
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