ANTIVIRAL OPTICALLY PURE DIOXOLANE PURINE NUCLEOSIDES ANALOGS

被引:22
作者
SIDDIQUI, MA
BROWN, WL
NGUYENBA, N
DIXIT, DM
MANSOUR, TS
HOOKER, E
VINER, KC
CAMERON, JM
机构
[1] BIOCHEM THERAPEUT, 531 BLVD PRAIRIES, LAVAL H7V 1B7, PQ, CANADA
[2] GLAXO GRP RES LTD, DEPT VIROL, GREENFORD RD, GREENFORD UB6 0HE, MIDDX, ENGLAND
关键词
D O I
10.1016/S0960-894X(00)80014-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Selective deamination of (+/-) ci., 2,6-diaminopurine dioxolane nucleoside produces the (-) guanine analogue having the 2R,4R absolute stereochemistry. The (+/-) cis-adenine analogue generates the 2R,4R hypoxanthinyl derivative. Asymmetric synthesis of purine dioxolanes have been developed. The (-) adenine and (-) guanine compounds 6 and 7 emerged as potent inhibitors of the HIV-1 replication in vitro.
引用
收藏
页码:1543 / 1546
页数:4
相关论文
共 19 条
[11]  
NORBECK DW, 1990, ANNU REP MED CHEM, V25, P149
[12]   NUCLEIC-ACID RELATED-COMPOUNDS .33. CONVERSIONS OF ADENOSINE AND GUANOSINE TO 2,6-DICHLORO, 2-AMINO-6-CHLORO, AND DERIVED PURINE NUCLEOSIDES [J].
ROBINS, MJ ;
UZNANSKI, B .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (17) :2601-2607
[13]  
SAUNDERS J, 1992, DRUG NEWS PERSPECT, V5, P153
[14]   INSIGHTS INTO HIV CHEMOTHERAPY [J].
SCHINAZI, RF ;
MEAD, JR ;
FEORINO, PM .
AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (06) :963-990
[15]  
SIDDIQUI MA, 1992, 2ND ONT QUEB MIN
[16]  
TSE HLA, COMMUNICATION
[17]   RESOLUTION OF RACEMIC CARBOVIR AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS BY THE (-) ENANTIOMER [J].
VINCE, R ;
BROWNELL, J .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 168 (03) :912-916
[18]  
WAINBERG MA, 1989, 5TH INT C AIDS MONTR, P552
[19]   NUCLEIC-ACID RELATED-COMPOUNDS .52. HIGH-YIELD REGIOSELECTIVE SYNTHESIS OF 9-GLYCOSYL GUANINE NUCLEOSIDES AND ANALOGS VIA COUPLING WITH 2-N-ACETYL-6-O-DIPHENYLCARBAMOYLGUANINE [J].
ZOU, R ;
ROBINS, MJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (06) :1436-1437