Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.
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.
Tron
Gian Cesare
GC
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale "A. Avogadro", Via Bovio 6, 28100 Novara, Italy. tron@pharm.unipmn.it
Pirali
Tracey
T
Billington
Richard A
RA
Canonico
Pier Luigi
PL
Sorba
Giovanni
G
Genazzani
Armando A
AA
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D015195:Drug Design; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis; D047028:Macrocyclic Compounds / Q000138:chemical synthesis; D014230:Triazoles / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D017320:HIV Protease Inhibitors; D047028:Macrocyclic Compounds; D014230:Triazoles; D003300:Copper