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

页码：597 / 601

页数：5

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