Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides

被引：37

作者：

Bortolini, Olga ^{[1
]}

De Nino, Antonio ^{[1
]}

Eliseo, Tommaso ^{[2
]}

Gavioli, Riccardo ^{[3
]}

Maiuolo, Loredana ^{[1
]}

Russo, Beatrice ^{[1
]}

Sforza, Fabio ^{[3
]}

机构：

[1] Univ Calabria, Dipartimento Chim, I-87036 Arcavacata Di Rende, CS, Italy

[2] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, Rome, Italy

[3] Univ Ferrara, Dipartimento Biochim & Biol Mol, I-44100 Ferrara, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 19期

关键词：

N; O-Nucleosides; 1,3-Dipolar cycloaddition; Cytotoxic activity; 1,3-DIPOLAR CYCLOADDITION REACTIONS; INVERSE-ELECTRON DEMAND; NUCLEOSIDE ANALOGS; NITRONES; DERIVATIVES; ISOXAZOLIDINES; 1,3-CYCLOADDITION; CONFIGURATION; DFT;

D O I：

10.1016/j.bmc.2010.08.024

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Several N,O-nucleosides have been synthesized in good yields by direct 1,3-dipolar cyclization methodology, in the absence of solvent. A remarkable cis stereoselectivity (de 98%) was observed by tuning the substituents on the nitrone moiety. A good number of these N, O-nucleosides have been evaluated for cytotoxic activity against selected cellular lines. Some of the tested compounds have proven to be potential antiproliferative drugs. (C) 2010 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6970 / 6976

页数：7

相关论文

共 39 条

[1] Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines [J].

Andrade, Marta M. ;

Barros, Maria Teresa ;

Pinto, Rui C. .

TETRAHEDRON, 2008, 64 (46) :10521-10530

[2] APPROACH TO THE VALORIZATION OF CARBOHYDRATES AS RAW MATERIALS BY MICROWAVE-ASSISTED NEAT 1,3-DIPOLAR CYCLOADDITION [J].

Andrade, Marta M. ;

Teresa Barros, Maria ;

Pinto, Rui C. .

SYNTHETIC COMMUNICATIONS, 2010, 40 (06) :855-860

[3] Absolute configuration of α-methylstyrene oxide:: The correct absolute configuration/optical rotation correlation [J].

Archelas, A ;

Furstoss, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6112-6114

[4] Nitrone derivatives of trolox as neuroprotective agents [J].

Balogh, GT ;

Vukics, K ;

Könczöl, A ;

Kis-Varga, A ;

Gere, A ;

Fischer, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3012-3015

[5] EFFECTS OF MODULATORS OF ADENYLYL CYCLASE ON INTERLEUKIN-2 PRODUCTION, CYTOSOLIC CA-2+ ELEVATION, AND K+ CHANNEL ACTIVITY IN JURKAT T-CELLS [J].

BASTIN, B ;

PAYET, MD ;

DUPUIS, G .

CELLULAR IMMUNOLOGY, 1990, 128 (02) :385-399

[6] Phosphinic platinum complexes with 8-thiotheophylline derivatives:: Synthesis, characterization, and antiproliferative activity [J].

Bergamini, P. ;

Bertolasi, V. ;

Marvelli, L. ;

Canella, A. ;

Gavioli, R. ;

Mantovani, N. ;

Manas, S. ;

Romerosa, A. .

INORGANIC CHEMISTRY, 2007, 46 (10) :4267-4276

[7] Identification and tissue-specific expression of PDE7 phosphodiesterase splice variants [J].

Bloom, TJ ;

Beavo, JA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (24) :14188-14192

[8] Solvent-free, microwave assisted 1,3-cycloaddition of nitrones with vinyl nucleobases for the synthesis of N,O-nucleosides [J].

Bortolini, Olga ;

D'Agostino, Maurizio ;

De Nino, Antonio ;

Maiuolo, Loredana ;

Nardi, Monica ;

Sindona, Giovanni .

TETRAHEDRON, 2008, 64 (35) :8078-8081

[9] 1,3-Cycloaddition of nitrones in ionic liquids catalyzed by Er(III): an easy access to isoxazolidines [J].

Bortolini, Olga ;

De Nino, Antonio ;

Maiuolo, Loredana ;

Russo, Beatrice ;

Sindona, Giovanni ;

Tocci, Amedeo .

TETRAHEDRON LETTERS, 2007, 48 (40) :7125-7128

[10] Synthesis of phosphonated carbocyclic 2′-oxa-3′-aza-nucleosides:: Novel inhibitors of reverse transcriptase [J].

Chiacchio, U ;

Balestrieri, E ;

Macchi, B ;

Iannazzo, D ;

Piperno, A ;

Rescifina, A ;

Romeo, R ;

Saglimbeni, M ;

Sciortino, MT ;

Valveri, V ;

Mastino, A ;

Romeo, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (05) :1389-1394

← 1 2 3 4 →