Are 5′-O-Carbamate-2′,3′-dideoxythiacytidine new anti-HIV and anti-HBV nucleoside drugs or prodrugs?

被引：13

作者：

Anastasi, C

Vlieghe, P

Hantz, O

Schorr, O

Pannecouque, C

Witvrouw, M

De Clercq, E

Clayette, P

Dereuddre-Bosquete, N

Dormont, D

Gondois-Rey, F

Hirsch, I

Kraus, JL

机构：

[1] Univ Aix Marseille 2, IBDM, Lab Chim Biomol, INSERM, F-13288 Marseille 9, France

[2] Labs LAPHAL, F-13718 Allauch, France

[3] INSERM, Unite Rech Hepatites Sida & Retrovirus Humains, U271, F-69424 Lyon 3, France

[4] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

[5] CEA, CRSSA, Serv Neurovirol, DSV,DRM, F-92265 Fontenay Aux Roses, France

[6] SPI BIO, F-91741 Massay, France

[7] INSERM, Unite Pathogenie Infect & Lentivirus, U372, F-13276 Marseille 9, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 15期

关键词：

D O I：

10.1016/S0960-894X(03)00496-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In contrast to 5'-O-carbonate 3TC derivatives (23, 24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (15-21 and 25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：2459 / 2463

页数：5

相关论文

共 13 条

[1] SYNTHESIS AND BIOLOGICAL EVALUATION OF PRODRUGS OF ZIDOVUDINE [J].

AGGARWAL, SK ;

GOGU, SR ;

RANGAN, SRS ;

AGRAWAL, KC .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1505-1510

[2] Synthesis and antiviral activity of amino acid carbamate derivatives of AZT [J].

Chang, SL ;

Griesgraber, G ;

Abraham, TW ;

Garg, T ;

Song, H ;

Zimmerman, CL ;

Wagner, CR .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (1-2) :87-100

[3] USE OF 2'-FLUORO-5-METHYL-BETA-L-ARABINOFURANOSYLURACIL AS A NOVEL ANTIVIRAL AGENT FOR HEPATITIS-B VIRUS AND EPSTEIN-BARR-VIRUS [J].

CHU, CK ;

MA, TW ;

SHANHMUGANATHAN, K ;

WANG, CG ;

XIANG, YJ ;

PAI, SB ;

YAO, GQ ;

SOMMADOSSI, JP ;

CHENG, YC .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) :979-981

[4] Fused bicyclic Gly-Asp β-turn mimics with potent affinity for GPIIb-IIIa.: Exploration of the arginine isostere [J].

Fisher, MJ ;

Giese, U ;

Harms, CS ;

Kinnick, MD ;

Lindstrom, TD ;

McCowan, JR ;

Mest, HJ ;

Morin, JM ;

Mullaney, JT ;

Paal, M ;

Rapp, A ;

Rühter, G ;

Ruterbories, KJ ;

Sall, DJ ;

Scarborough, RM ;

Schotten, T ;

Stenzel, W ;

Towner, RD ;

Um, SL ;

Utterback, BG ;

Wyss, VL ;

Jakubowski, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (04) :385-389

[5] Optimization and mechanistic analysis of oligonucleotide cleavage from palladium-labile solid-phase synthesis supports [J].

Greenberg, MM ;

Matray, TJ ;

Kahl, JD ;

Yoo, DJ ;

McMinn, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :4062-4068

[6]

KAZMIERSKI W, 2002, 223 NAT M AM CHEM SO

[7] A novel class of zinc-binding inhibitors for the phosphatidylcholine-preferring phospholipase C from Bacillus cereus [J].

Martin, SF ;

Follows, BC ;

Hergenrother, PJ ;

Franklin, CL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4509-4514

[8] Probing the mechanism of action and decomposition of amino acid phosphomonoester amidates of antiviral nucleoside prodrugs [J].

McIntee, EJ ;

Remmel, RP ;

Schinazi, RF ;

Abraham, TW ;

Wagner, CR .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3323-3331

[9] RAPID AND AUTOMATED TETRAZOLIUM-BASED COLORIMETRIC ASSAY FOR THE DETECTION OF ANTI-HIV COMPOUNDS [J].

PAUWELS, R ;

BALZARINI, J ;

BABA, M ;

SNOECK, R ;

SCHOLS, D ;

HERDEWIJN, P ;

DESMYTER, J ;

DECLERCQ, E .

JOURNAL OF VIROLOGICAL METHODS, 1988, 20 (04) :309-321

[10]

Perez-Perez M J, 1993, Bioorg Med Chem, V1, P279, DOI 10.1016/S0968-0896(00)82133-1