PREPARATION AND ANTI-HIV ACTIVITY OF N-3 AMINO SUBSTITUTED THYMIDINE NUCLEOSIDE ANALOGS

被引：9

作者：

MAILLARD, M

FLORENT, JC

LEMAITRE, M

BEGASSAT, F

BUGNICOURT, A

FERRIEUX, C

ROMBI, C

PACAUD, E

THIERRY, D

ZERIAL, A

MONNERET, C

GRIERSON, DS

机构：

[1] INST CURIE,SERV CHIM,BIOL SECT,CNRS,URA 1387,26 RUE ULM,PARIS 05,FRANCE

[2] INST CHIM SUBST NAT,CNRS,F-91198 GIF SUR YVETTE,FRANCE

[3] RHONE POULENC RORER SA,CVRA,F-94403 VITRY,FRANCE

[4] CBN,IPSN,SARAM,F-92260 FONTENAY ROSES,FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 12期

关键词：

D O I：

10.1016/S0960-894X(00)80410-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The N-3 amino derivatives 7-10 of ddT, AZT, 3'-FddT, and D4T were prepared by electrophilic amination of the parent compounds. Although compounds 7, 9, and 10 were essentially inactive, N-3 amino AZT 8 (RP67042) maintained activity and displayed lower toxicity and a longer plasmatic halflife compared to AZT..

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页码：1469 / 1474

页数：6

相关论文

共 18 条

[1] ANTI-RETROVIRUS ACTIVITY OF 3'-FLUORO-SUBSTITUTED AND 3'-AZIDO-SUBSTITUTED PYRIMIDINE 2',3'-DIDEOXYNUCLEOSIDE ANALOGS [J].

BALZARINI, J ;

BABA, M ;

PAUWELS, R ;

HERDEWIJN, P ;

DECLERCO, E .

BIOCHEMICAL PHARMACOLOGY, 1988, 37 (14) :2847-2856

[2] ISOLATION OF A T-LYMPHOTROPIC RETROVIRUS FROM A PATIENT AT RISK FOR ACQUIRED IMMUNE-DEFICIENCY SYNDROME (AIDS) [J].

BARRESINOUSSI, F ;

CHERMANN, JC ;

REY, F ;

NUGEYRE, MT ;

CHAMARET, S ;

GRUEST, J ;

DAUGUET, C ;

AXLERBLIN, C ;

VEZINETBRUN, F ;

ROUZIOUX, C ;

ROZENBAUM, W ;

MONTAGNIER, L .

SCIENCE, 1983, 220 (4599) :868-871

[3]

CHU CK, 1988, Z BIOCH PHARM, V37, P3343

[4] DIRECT, SELECTIVE, AND GENERAL METHOD FOR REDUCTIVE DEAMINATION OF PRIMARY AMINES [J].

DOLDOURAS, GA ;

KOLLONITSCH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :341-342

[5]

GRIERSON DS, 1991, Patent No. 437382

[6] ENHANCED INVITRO INHIBITION OF HIV-1 REPLICATION BY 3'-FLUORO-3'-DEOXYTHYMIDINE COMPARED TO SEVERAL OTHER NUCLEOSIDE ANALOGS [J].

HARTMANN, H ;

VOGT, MW ;

DURNO, AG ;

HIRSCH, MS ;

HUNSMANN, G ;

ECKSTEIN, F .

AIDS RESEARCH AND HUMAN RETROVIRUSES, 1988, 4 (06) :457-466

[7] 3'-SUBSTITUTED 2',3'-DIDEOXYNUCLEOSIDE ANALOGS AS POTENTIAL ANTI-HIV (HTLV-III/LAV) AGENTS [J].

HERDEWIJN, P ;

BALZARINI, J ;

DECLERCQ, E ;

PAUWELS, R ;

BABA, M ;

BRODER, S ;

VANDERHAEGHE, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1270-1278

[8]

KITADE Y, 1992, CHEM PHARM BULL, V40, P920

[9] STRUCTURE-ACTIVITY-RELATIONSHIPS OF FLUORINATED NUCLEOSIDE ANALOGS AND THEIR SYNERGISTIC EFFECT IN COMBINATION WITH PHOSPHONOFORMATE AGAINST HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 [J].

KOSHIDA, R ;

COX, S ;

HARMENBERG, J ;

GILLJAM, G ;

WAHREN, B .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1989, 33 (12) :2083-2088

[10] SYNTHESIS AND ANTIVIRAL ACTIVITY OF VARIOUS 3'-AZIDO, 3'-AMINO, 2',3'-UNSATURATED, AND 2',3'-DIDEOXY ANALOGS OF PYRIMIDINE DEOXYRIBONUCLEOSIDES AGAINST RETROVIRUSES [J].

LIN, TS ;

CHEN, MS ;

MCLAREN, C ;

GAO, YS ;

GHAZZOULI, I ;

PRUSOFF, WH .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :440-444