Azidonucleosides:  Synthesis, Reactions, and Biological Properties

Pathak, Tanmaya

doi:10.1021/cr0104532

Cited by 156 publications

(60 citation statements)

References 298 publications

(554 reference statements)

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“…Industrial relevance of organic azides began with their application as intermediates in organic synthesis [8,9]. They also become important precursors for nitrenes, used in both nitride film depositioná [10,á11]áandásidewalláfunctionalizationáofásingle-wallácarbonánanotubesá(SWNTs)á [12,á13].áPharmaceuti-cal applications include the anti-HIV medication AZT (3=azido-2=,3=-didesoxy-thymidine)á [14]áandátuberculo-sisámedicationá [15].áSomeáorganicáazidesáhaveáseveral features that make them suitable for tagging biological moleculesá [16,á17].…”

mentioning

confidence: 99%

Complexation of transition metals by 3-azidopropionitrile. An electrospray ionization mass spectrometry study

Couto

Duarte

Fernandez

et al. 2007

J. Am. Soc. Mass Spectrom.

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Most complexes of azides and transition metals involve the N 3Ϫ azide anion as a ligand other than an organic azide. Complexes of organic azides with metals are involved in biological applications and in the deposition of nitrenes on metal surfaces, producing nitride layers for semi-conductors preparation; this makes the study of these interactions an important issue. This work describes a study of the complexation of nickel and cobalt by 3-azidopropionitrile by means of electrospray ionization mass spectrometry (ESI-MS). Complexes were obtained from solutions of NiCl 2 and CoCl 2 in methanol/water. In the case of nickel, other NiX 2 salts were investigated (where X ϭ Br or NO 3 ) and other solvents were also studied (notably ethanol/water). All complexes detected were single positively charged, with various stoichiometries, some resulted from the fragmentation of the ligand, the loss of N 2 , and HCN being quite common. The most abundant cations observed were [Ni(II)AzAzX] ϩ , where X ϭ Cl, Br, NO 3 . Some of the complexes showed solvation with methanol/ethanol/water. Metal reduction was observed in complexes where a radical was lost, resulting from the homolytic cleavage of a metalOnitrogen bond. Collision induced dissociation (CID) experiments followed by tandem mass spectrometry (MS-MS) analysis were not absolutely conclusive about the coordination site. However, terminal ions observed from the fragmentation routes were explained by a proposed gas-phase mechanism. Density functional theory calculations were carried out and provided structures for some complexes, pointing to the possibility of 3-azidopropionitrile acting as a mono-or a bidentate ligand. (J Am Soc Mass Spectrom 2007, 18, 453-465)

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mentioning

confidence: 99%

Complexation of transition metals by 3-azidopropionitrile. An electrospray ionization mass spectrometry study

Couto

Duarte

Fernandez

et al. 2007

J. Am. Soc. Mass Spectrom.

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“…These are the syntheses with the reduction of 3'-azido-3'-deoxythymidine [7][8][9][16][17][18][19][20][21][22][23][24] and syntheses through the alkylation of various nitrogen-containing compounds by 3'-sulfonate derivatives of thymidine [25].…”

Section: Resultsmentioning

confidence: 99%

“…The reduction with triphenylphosphine attached to a polymer matrix (70%) has also been described [23]. A more detailed information on the methods of reduction of azidonucleosides to aminonucleosides can be found in review [24].…”

Section: Resultsmentioning

confidence: 99%

An efficient synthesis of 3′-amino-3′-deoxythymidine derivatives

Chudinov

et al. 2005

Russ J Bioorg Chem

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“…[1][2][3][4] Consequently, improved and abbreviated synthesis of modified nucleosides from readily available precursors is of considerable interest. [5][6][7][8][9] However, nucleosides are challenging synthetic substrates as they contain several functionalized groups that must be chemically differentiated for successful transformations. Therefore, multi-step synthesis frequently requires the introduction of protective groups and their subsequent removal.…”

Section: Introductionmentioning

confidence: 99%

Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

Meier¹,

Monteiro²,

Baldissera³

et al. 2010

J. Braz. Chem. Soc.

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Este trabalho apresenta um método simples, rápido e eficiente para a desacetilação de ribonucleosídeos acetilados, a partir de metanólise catalisada por trietilamina em meio aquoso. As transformações assistidas por micro-ondas favoreceram sensivelmente a velocidade de reação e forneceram os nucleosídeos desprotegidos em altos rendimentos e sob condições brandas. Além de tolerar a presença de diversos grupos funcionais e de fornecer produtos com alto grau de pureza, esta nova metodologia utiliza reagentes de baixo custo e toxicidade.A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.

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Azidonucleosides: Synthesis, Reactions, and Biological Properties

Cited by 156 publications

References 298 publications

Complexation of transition metals by 3-azidopropionitrile. An electrospray ionization mass spectrometry study

Complexation of transition metals by 3-azidopropionitrile. An electrospray ionization mass spectrometry study

An efficient synthesis of 3′-amino-3′-deoxythymidine derivatives

Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

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