HOMOLOGS OF ANTI-HIV ACTIVE ISODIDEOXYNUCLEOSIDES

被引:12
作者
BOLON, P [1 ]
JAHNKE, TS [1 ]
NAIR, V [1 ]
机构
[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
基金
美国国家卫生研究院;
关键词
ISODIDEOXYNUCLEOSIDES; HOMOLOGS; CONVERGENT SYNTHESIS; ANTI-HIV;
D O I
10.1016/0040-4020(95)00626-J
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a homologous series of compounds related to the anti-HN active class of compounds known as (S,S)-isodideoxynucleosides has been completed by a convergent route using a modified carbohydrate intermediate. This precursor, synthesized from D-glucose, was coupled with a variety of natural purine and pyrimidine bases to regiospecifically and stereospecifically afford the desired new class of compounds.
引用
收藏
页码:10443 / 10452
页数:10
相关论文
共 28 条
[1]   SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
AGROFOGLIO, L ;
SUHAS, E ;
FARESE, A ;
CONDOM, R ;
CHALLAND, SR ;
EARL, RA ;
GUEDJ, R .
TETRAHEDRON, 1994, 50 (36) :10611-10670
[2]   SYNTHESIS OF (+/-)-2'-OXA-CARBOCYCLIC-2',3'-DIDEOXYNUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS [J].
BAMFORD, MJ ;
HUMBER, DC ;
STORER, R .
TETRAHEDRON LETTERS, 1991, 32 (02) :271-274
[3]   REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .7. CONVERSION OF THIOCARBONATES INTO DEOXY-SUGARS [J].
BARTON, DHR ;
SUBRAMANIAN, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (15) :1718-1723
[5]   AN EFFICIENT SYNTHESIS OF ANHYDROALDITOLS AND ALLYL C-GLYCOSIDES [J].
BENNEK, JA ;
GRAY, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :892-897
[6]   NOVEL ISOMERIC DIDEOXYNUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS [J].
BOLON, PJ ;
SELLS, TB ;
NUESCA, ZM ;
PURDY, DF ;
NAIR, V .
TETRAHEDRON, 1994, 50 (26) :7747-7764
[7]  
CHU C K, 1991, Journal of Organic Chemistry, V56, P6503, DOI 10.1021/jo00023a010
[8]   THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO [J].
COATES, JAV ;
CAMMACK, N ;
JENKINSON, HJ ;
MUTTON, IM ;
PEARSON, BA ;
STORER, R ;
CAMERON, JM ;
PENN, CR .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) :202-205
[9]   HIV RESISTANCE TO REVERSE-TRANSCRIPTASE INHIBITORS [J].
DECLERCQ, E .
BIOCHEMICAL PHARMACOLOGY, 1994, 47 (02) :155-169
[10]   ANTIVIRAL ACTIVITY SPECTRUM AND TARGET OF ACTION OF DIFFERENT CLASSES OF NUCLEOSIDE ANALOGS [J].
DECLERCQ, E .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1994, 13 (6-7) :1271-1295