Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases

被引：10

作者：

Amblard, Franck ^{[1
]}

Fromentin, Emilie ^{[1
]}

Detorio, Mervi ^{[1
]}

Obikhod, Alexander ^{[1
]}

Rapp, Kimberly L. ^{[1
]}

McBrayer, Tamara R. ^{[2
]}

Whitaker, Tony ^{[2
]}

Coats, Steven J. ^{[2
]}

Schinazi, Raymond F. ^{[1
]}

机构：

[1] Emory Univ, Sch Med, Dept Pediat, Ctr AIDS Res,Vet Affairs Med Ctr,Lab Biochem Phar, Atlanta, GA 30033 USA

[2] RFS Pharma LLC, Tucker, GA 30084 USA

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 10期

关键词：

Nucleosides; Tricyclic; Stability; ACYCLOVIR; GANCICLOVIR; DERIVATIVES; INHIBITION; EFFICIENT; VIRUSES;

D O I：

10.1016/j.ejmech.2009.04.003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine nucleosides (tricylic nucleosides) were synthesized from 9-[4-alpha(hydroxymethyl)cyclopent-2-ene-l-alpha-yl]guanine (CBV) 5, (-)-beta-D-(2R,4R)-1,3-dioxo-lane-guanosine (DXG) 6, 3'-azido-3'-deoxy-guanosine (AZG) 7, and 2'-C-methylguanosine 8. Their in vitro activity against HIV and HCV was evaluated and correlated to their ability to degrade to their purine Counterpart. (C) 2009 Elsevier Masson SAS. All rights reserved.

引用

页码：3845 / 3851

页数：7

共 30 条

[1] Pronounced cytostatic activity and bystander effect of a novel series of fluorescent tricyclic acyclovir and ganciclovir derivatives in herpes simplex virus thymidine kinase gene-transduced tumor cell lines [J].

Balzarini, J ;

Ostrowski, T ;

Goslinski, T ;

De Clercq, E ;

Golankiewicz, B .

GENE THERAPY, 2002, 9 (17) :1173-1182

[2] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3-SUBSTITUTED DERIVATIVES OF 3,9-DIHYDRO-9-OXO-5H-IMIDAZO[1,2-A]PURINES, TRICYCLIC ANALOGS OF ACYCLOVIR AND GANCICLOVIR [J].

BORYSKI, J ;

GOLANKIEWICZ, B ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2380-2383

[3] Design, synthesis, and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication [J].

Clark, JL ;

Hollecker, L ;

Mason, JC ;

Stuyver, LJ ;

Tharnish, PM ;

Lostia, S ;

McBrayer, TR ;

Schinazi, RF ;

Watanabe, KA ;

Otto, MJ ;

Furman, PA ;

Stec, WJ ;

Patterson, SE ;

Pankiewiez, KW .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5504-5508

[4] An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen® (1592U89) [J].

Daluge, SM ;

Martin, MT ;

Sickles, BR ;

Livingston, DA .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (1-2) :297-327

[5] Current therapy for chronic hepatitis C [J].

Davis, GL .

GASTROENTEROLOGY, 2000, 118 (02) :S104-S114

[6] Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase [J].

Eldrup, AB ;

Allerson, CR ;

Bennett, CF ;

Bera, S ;

Bhat, B ;

Bhat, N ;

Bosserman, MR ;

Brooks, J ;

Burlein, C ;

Carroll, SS ;

Cook, PD ;

Getty, KL ;

MacCoss, M ;

McMasters, DR ;

Olsen, DB ;

Prakash, TP ;

Prhavc, M ;

Song, QL ;

Tomassini, JE ;

Xia, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (09) :2283-2295

[7] Fluorescent tricyclic analogues of acyclovir and ganciclovir. A structure-antiviral activity study [J].

Golankiewicz, B ;

Ostrowski, T ;

Goslinski, T ;

Januszczyk, P ;

Zeidler, J ;

Baranowski, D ;

de Clercq, E .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (24) :4284-4287

[8] TRICYCLIC ANALOGS OF ACYCLOVIR AND GANCICLOVIR - INFLUENCE OF SUBSTITUENTS IN THE HETEROCYCLIC MOIETY ON THE ANTIVIRAL ACTIVITY [J].

GOLANKIEWICZ, B ;

OSTROWSKI, T ;

ANDREI, G ;

SNOECK, R ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (19) :3187-3190

[9] Tricyclic nucleoside analogues as antiherpes agents [J].

Golankiewicz, Bozenna ;

Ostrowski, Tomasz .

ANTIVIRAL RESEARCH, 2006, 71 (2-3) :134-140

[10]

GOLINSKI T, 2005, NUCLEOS NUCLEOT, P571

← 1 2 3 →