1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies
The synthesis of hybrid molecules is one of the current strategies of drug discovery for the development of new lead compounds. The 1,2,3-triazole moiety represents an important building block in Medicinal Chemistry, extensively present in recent years. In this paper, we presented the design and the...
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| Format: | Article |
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MDPI AG
2024-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/7/1556 |
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| author | Loredana Maiuolo Matteo Antonio Tallarida Angelo Meduri Giulia Fiorani Antonio Jiritano Antonio De Nino Vincenzo Algieri Paola Costanzo |
| author_facet | Loredana Maiuolo Matteo Antonio Tallarida Angelo Meduri Giulia Fiorani Antonio Jiritano Antonio De Nino Vincenzo Algieri Paola Costanzo |
| author_sort | Loredana Maiuolo |
| collection | DOAJ |
| description | The synthesis of hybrid molecules is one of the current strategies of drug discovery for the development of new lead compounds. The 1,2,3-triazole moiety represents an important building block in Medicinal Chemistry, extensively present in recent years. In this paper, we presented the design and the synthesis of new 1,2,3-triazole hybrids, containing both an isatine and a phenolic core. Firstly, the non-commercial azide and the alkyne synthons were prepared by different isatines and phenolic acids, respectively. Then, the highly regioselective synthesis of 1,4-disubstituted triazoles was obtained in excellent yields by a click chemistry approach, catalyzed by Cu(I). Finally, a molecular docking study was performed on the hybrid library, finding four different therapeutic targets. Among them, the most promising results were obtained on 5-lipoxygenase, an enzyme involved in the inflammatory processes. |
| first_indexed | 2024-04-24T10:38:53Z |
| format | Article |
| id | doaj.art-37389a38b03e428d943279a00e46ddea |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-24T10:38:53Z |
| publishDate | 2024-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-37389a38b03e428d943279a00e46ddea2024-04-12T13:23:23ZengMDPI AGMolecules1420-30492024-03-01297155610.3390/molecules290715561,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking StudiesLoredana Maiuolo0Matteo Antonio Tallarida1Angelo Meduri2Giulia Fiorani3Antonio Jiritano4Antonio De Nino5Vincenzo Algieri6Paola Costanzo7Department of Chemistry and Chemical Technologies, University of Calabria, 87036 Rende, ItalyRINA Consulting—Centro Sviluppo Materiali SpA, Via di Castel Romano 100, 00128 Rome, ItalyRINA Consulting—Centro Sviluppo Materiali SpA, Zona Industriale San Pietro Lametino, Comparto 1, 88046 Lamezia Terme, CZ, ItalyDepartment Molecular Sciences and Nanosystems, University Ca’ Foscari Venezia, 30172 Mestre, VE, ItalyDepartment of Chemistry and Chemical Technologies, University of Calabria, 87036 Rende, ItalyDepartment of Chemistry and Chemical Technologies, University of Calabria, 87036 Rende, ItalyIRCCS NEUROMED—Istituto Neurologico Mediterraneo, Via Atinense 18, 86077 Pozzilli, IS, ItalyDepartment of Chemistry and Chemical Technologies, University of Calabria, 87036 Rende, ItalyThe synthesis of hybrid molecules is one of the current strategies of drug discovery for the development of new lead compounds. The 1,2,3-triazole moiety represents an important building block in Medicinal Chemistry, extensively present in recent years. In this paper, we presented the design and the synthesis of new 1,2,3-triazole hybrids, containing both an isatine and a phenolic core. Firstly, the non-commercial azide and the alkyne synthons were prepared by different isatines and phenolic acids, respectively. Then, the highly regioselective synthesis of 1,4-disubstituted triazoles was obtained in excellent yields by a click chemistry approach, catalyzed by Cu(I). Finally, a molecular docking study was performed on the hybrid library, finding four different therapeutic targets. Among them, the most promising results were obtained on 5-lipoxygenase, an enzyme involved in the inflammatory processes.https://www.mdpi.com/1420-3049/29/7/1556triazole hybridsisatin hybridsCuAAC |
| spellingShingle | Loredana Maiuolo Matteo Antonio Tallarida Angelo Meduri Giulia Fiorani Antonio Jiritano Antonio De Nino Vincenzo Algieri Paola Costanzo 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies Molecules triazole hybrids isatin hybrids CuAAC |
| title | 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies |
| title_full | 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies |
| title_fullStr | 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies |
| title_full_unstemmed | 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies |
| title_short | 1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies |
| title_sort | 1 2 3 triazole hybrids containing isatins and phenolic moieties regioselective synthesis and molecular docking studies |
| topic | triazole hybrids isatin hybrids CuAAC |
| url | https://www.mdpi.com/1420-3049/29/7/1556 |
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