Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.

Gian Cesare Tron; Tracey Pirali; Richard A. Billington; Pier Luigi Canonico; Giovanni Sorba; Armando A. Genazzani

doi:10.1002/med.20107

Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.

Gian Cesare Tron^*, Tracey Pirali, Richard A. Billington, Pier Luigi Canonico, Giovanni Sorba, Armando A. Genazzani

^*Corresponding author for this work

School of Biological and Marine Sciences

University of Eastern Piedmont

Research output: Contribution to journal › Article › peer-review

Abstract

In recent years, there has been an ever-increasing need for rapid reactions that meet the three main criteria of an ideal synthesis: efficiency, versatility, and selectivity. Such reactions would allow medicinal chemistry to keep pace with the multitude of information derived from modern biological screening techniques. The present review describes one of these reactions, the 1,3-dipolar cycloaddition ("click-reaction") between azides and alkynes catalyzed by copper (I) salts. The simplicity of this reaction and the ease of purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The present review will outline the accomplishments of this strategy achieved so far and outline some of medicinal chemistry applications in which click-chemistry might be relevant in the future.

Original language	English
Pages (from-to)	278-308
Number of pages	0
Journal	Med Res Rev
Volume	28
Issue number	2
DOIs	https://doi.org/10.1002/med.20107
Publication status	Published - Mar 2008

Keywords

Alkynes
Azides
Catalysis
Combinatorial Chemistry Techniques
Copper
Cyclization
Dimerization
Drug Design
HIV Protease Inhibitors
Macrocyclic Compounds
Triazoles

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title = "Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.",

abstract = "In recent years, there has been an ever-increasing need for rapid reactions that meet the three main criteria of an ideal synthesis: efficiency, versatility, and selectivity. Such reactions would allow medicinal chemistry to keep pace with the multitude of information derived from modern biological screening techniques. The present review describes one of these reactions, the 1,3-dipolar cycloaddition ({"}click-reaction{"}) between azides and alkynes catalyzed by copper (I) salts. The simplicity of this reaction and the ease of purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The present review will outline the accomplishments of this strategy achieved so far and outline some of medicinal chemistry applications in which click-chemistry might be relevant in the future.",

keywords = "Alkynes, Azides, Catalysis, Combinatorial Chemistry Techniques, Copper, Cyclization, Dimerization, Drug Design, HIV Protease Inhibitors, Macrocyclic Compounds, Triazoles",

author = "Tron, {Gian Cesare} and Tracey Pirali and Billington, {Richard A.} and Canonico, {Pier Luigi} and Giovanni Sorba and Genazzani, {Armando A.}",

year = "2008",

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doi = "10.1002/med.20107",

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T1 - Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.

AU - Tron, Gian Cesare

AU - Pirali, Tracey

AU - Billington, Richard A.

AU - Canonico, Pier Luigi

AU - Sorba, Giovanni

AU - Genazzani, Armando A.

PY - 2008/3

Y1 - 2008/3

N2 - In recent years, there has been an ever-increasing need for rapid reactions that meet the three main criteria of an ideal synthesis: efficiency, versatility, and selectivity. Such reactions would allow medicinal chemistry to keep pace with the multitude of information derived from modern biological screening techniques. The present review describes one of these reactions, the 1,3-dipolar cycloaddition ("click-reaction") between azides and alkynes catalyzed by copper (I) salts. The simplicity of this reaction and the ease of purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The present review will outline the accomplishments of this strategy achieved so far and outline some of medicinal chemistry applications in which click-chemistry might be relevant in the future.

AB - In recent years, there has been an ever-increasing need for rapid reactions that meet the three main criteria of an ideal synthesis: efficiency, versatility, and selectivity. Such reactions would allow medicinal chemistry to keep pace with the multitude of information derived from modern biological screening techniques. The present review describes one of these reactions, the 1,3-dipolar cycloaddition ("click-reaction") between azides and alkynes catalyzed by copper (I) salts. The simplicity of this reaction and the ease of purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The present review will outline the accomplishments of this strategy achieved so far and outline some of medicinal chemistry applications in which click-chemistry might be relevant in the future.

KW - Alkynes

KW - Azides

KW - Catalysis

KW - Combinatorial Chemistry Techniques

KW - Copper

KW - Cyclization

KW - Dimerization

KW - Drug Design

KW - HIV Protease Inhibitors

KW - Macrocyclic Compounds

KW - Triazoles

U2 - 10.1002/med.20107

DO - 10.1002/med.20107

M3 - Article

SN - 0198-6325

VL - 28

SP - 278

EP - 308

JO - Med Res Rev

JF - Med Res Rev

IS - 2

ER -

Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.

Abstract

Keywords

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