Bioactive fused heterocycles: Nucleoside analogs with an additional ring

被引：46

作者：

Jahnz-Wechmann, Zofia ^{[1
]}

Framski, Grzegorz ^{[1
]}

Januszczyk, Piotr ^{[1
]}

Boryski, Jerzy ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Bioorgan Chem, PL-61704 Poznan, Poland

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2015年 / 97卷

关键词：

Fused heterocycles; Bioactive nucleosides; Ethenonucleosides; Furano[2,3-d]pyrimidine nucleosides; Pyrrolo[2,3-d]pyrimidine nucleosides; Antiviral activity; VARICELLA-ZOSTER-VIRUS; ACID RELATED-COMPOUNDS; BICYCLIC PYRIMIDINE NUCLEOSIDE; FLUORESCENT TRICYCLIC ANALOGS; ANTIVIRAL ACTIVITY; NUCLEIC-ACID; BIOLOGICAL EVALUATION; HIGHLY POTENT; SELECTIVE-INHIBITION; NUCLEOTIDE ANALOGS;

D O I：

10.1016/j.ejmech.2014.12.026

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The following mini-review summarizes the basic literature data regarding synthesis, biological activity, structure-activity relationship, and discussion of the mechanisms of action of two major classes of nucleoside analogs with fused heterocyclic rings: (i) the ethenonucleosides and their related derivatives of the 5,9-dihydro-3-glycosyl-6-alkyl-9-oxo-5H-imidazo[1,2-a]purine type; (ii) the bicyclic nucleosides of 6-alkyl-2,3-dihydrofurano[2,3-d]-pyrimidin-2(3H)-one and 6-alkyl-2,3-dihydropyrrolo[2,3-d]-pyrimidin-2(3H,7H)-one. (C) 2015 Elsevier Masson SAS. All rights reserved.

引用

页码：388 / 396

页数：9

共 88 条

[1] Furano- and pyrrolo[2,3-D]pyrimidine nucleosides and their 5′-O-triphosphates:: Synthesis and enzymatic activity [J].

Alexandrova, L. A. ;

Ivanov, M. A. ;

Victorova, L. S. ;

Kukhanova, M. K. .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (8-9) :1083-1086

[2] Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series [J].

Amblard, F ;

Aucagne, V ;

Guenot, P ;

Schinazi, RF ;

Agrofoglio, LA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (04) :1239-1248

[3] Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases [J].

Amblard, Franck ;

Fromentin, Emilie ;

Detorio, Mervi ;

Obikhod, Alexander ;

Rapp, Kimberly L. ;

McBrayer, Tamara R. ;

Whitaker, Tony ;

Coats, Steven J. ;

Schinazi, Raymond F. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) :3845-3851

[4] Susceptibilities of several clinical Varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides [J].

Andrei, G ;

Sienaert, R ;

McGuigan, C ;

De Clercq, E ;

Balzarini, J ;

Snoeck, R .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (03) :1081-1086

[5]

Andrei G, 2013, ADV PHARMACOL, V67, P107, DOI 10.1016/B978-0-12-405880-4.00004-4

[6] Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides [J].

Balzarini, J ;

McGuigan, C .

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR BASIS OF DISEASE, 2002, 1587 (2-3) :287-295

[7] 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

[8] FLUORESCENT ADENOSINE AND CYTIDINE DERIVATIVES [J].

BARRIO, JR ;

SECRIST, JA ;

LEONARD, NJ .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1972, 46 (02) :597-&

[9] AN EFFICIENT SYNTHESIS OF Y-NUCLEOSIDE (WYOSINE) BY REGIOSPECIFIC METHYLATION OF N-4-DESMETHYLWYOSINE USING ORGANOZINC REAGENT [J].

BAZIN, H ;

ZHOU, XX ;

GLEMAREC, C ;

CHATTOPADHYAYA, J .

TETRAHEDRON LETTERS, 1987, 28 (28) :3275-3278

[10] NEW OBSERVATIONS CONCERNING CHLOROACETALDEHYDE REACTION WITH SOME TRANSFER-RNA CONSTITUENTS - STABLE INTERMEDIATES, KINETICS AND SELECTIVITY OF REACTION [J].

BIERNAT, J ;

CIESIOLKA, J ;

GORNICKI, P ;

ADAMIAK, RW ;

KRZYZOSIAK, WJ ;

WIEWIOROWSKI, M .

NUCLEIC ACIDS RESEARCH, 1978, 5 (03) :789-804

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