The 1,2,3-triazole ring as a bioisostere in medicinal chemistry
•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 recen...
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| Published in: | Drug discovery today Vol. 22; no. 10; pp. 1572 - 1581 |
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| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
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England
Elsevier Ltd
01-10-2017
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| Abstract | •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. |
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| AbstractList | 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. •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. |
| Author | Fumagalli, Gaia Rastelli, Giulio Bonandi, Elisa Christodoulou, Michael S. Passarella, Daniele Perdicchia, Dario |
| Author_xml | – sequence: 1 givenname: Elisa surname: Bonandi fullname: Bonandi, Elisa organization: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy – sequence: 2 givenname: Michael S. surname: Christodoulou fullname: Christodoulou, Michael S. organization: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy – sequence: 3 givenname: Gaia surname: Fumagalli fullname: Fumagalli, Gaia organization: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy – sequence: 4 givenname: Dario surname: Perdicchia fullname: Perdicchia, Dario organization: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy – sequence: 5 givenname: Giulio surname: Rastelli fullname: Rastelli, Giulio organization: Dipartimento di Scienze della Vita, Università degli Studi di Modena e Reggio Emilia, Via Campi 103, 41125 Modena, Italy – sequence: 6 givenname: Daniele surname: Passarella fullname: Passarella, Daniele email: daniele.passarella@unimi.it organization: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28676407$$D View this record in MEDLINE/PubMed |
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| Snippet | •Triazoles mimic different functional groups, resulting optimal bioisosteres for the synthesis of new active molecules.•Triazoles present a marked stability... 1,2,3-Triazole is a well-known scaffold that has a widespread occurrence in different compounds characterized by several bioactivities, such as antimicrobial,... |
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| SubjectTerms | Anti-Bacterial Agents - chemistry Antineoplastic Agents - chemistry Antiviral Agents - chemistry Chemistry, Pharmaceutical - methods Humans Triazoles - chemistry |
| Title | The 1,2,3-triazole ring as a bioisostere in medicinal chemistry |
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