The 1,2,3-triazole ring as a bioisostere in medicinal chemistry

• Published in: Drug discovery today Vol. 22; no. 10; pp. 1572 - 1581
• Main Authors: Bonandi, Elisa, Christodoulou, Michael S., Fumagalli, Gaia, Perdicchia, Dario, Rastelli, Giulio, Passarella, Daniele
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-10-2017
• Subjects: Anti-Bacterial Agents - chemistry; Antineoplastic Agents - chemistry; Antiviral Agents - chemistry; Chemistry, Pharmaceutical - methods; Humans; Triazoles - chemistry
• ISSN: 1359-6446; 1878-5832
• DOI: 10.1016/j.drudis.2017.05.014

•Triazoles mimic different functional groups, resulting optimal bioisosteres for the synthesis of new active molecules.•Triazoles present a marked stability under hydrolytic, oxidative and reductive conditions.•New highly regioselective synthetic methodologies for triazoles synthesis have been recently developed.•Among the plethora of the selected examples of bioisosterism, the amide bond replacement is clearly a predominant approach.
1,2,3-Triazole is a well-known scaffold that has a widespread occurrence in different compounds characterized by several bioactivities, such as antimicrobial, antiviral, and antitumor effects. Moreover, the structural features of 1,2,3-triazole enable it to mimic different functional groups, justifying its wide use as a bioisostere for the synthesis of new active molecules. Here, we provide an overview of the 1,2,3-triazole ring as a bioisostere for the design of drug analogs, highlighting relevant recent examples.