Please use this identifier to cite or link to this item:
http://hdl.handle.net/10773/40423
Title: | Facile Access to Structurally Diverse Antimalarial Indoles Using a One-Pot A3 Coupling and Domino Cyclization Approach |
Author: | da Silva, Gustavo Luz, André F. S. Duarte, Denise Fontinha, Diana Silva, Vera L. M. Almeida Paz, Filipe A. Madureira, Ana M. Simões, Sandra Prudêncio, Miguel Nogueira, Fátima Silva, Artur M. S. Moreira, Rui |
Keywords: | A3 coupling Antimalarials Indoles Multicomponent reactions One-pot synthesis |
Issue Date: | 1-Sep-2023 |
Publisher: | Wiley-Blackwell |
Abstract: | A multistep and diversity-oriented synthetic route aiming at the A3 coupling/domino cyclization of o-ethynyl anilines, aldehydes and s-amines is described. The preparation of the corresponding precursors included a series of transformations, such as haloperoxidation and Sonogashira cross-coupling reactions, amine protection, desilylation and amine reduction. Some products of the multicomponent reaction underwent further detosylation and Suzuki coupling. The resulting library of structurally diverse compounds was evaluated against blood and liver stage malaria parasites, which revealed a promising lead with sub-micromolar activity against intra-erythrocytic forms of Plasmodium falciparum. The results from this hit-to-lead optimization are hereby reported for the first time. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/40423 |
DOI: | 10.1002/cmdc.202300264 |
ISSN: | 1860-7179 |
Appears in Collections: | CICECO - Artigos DQ - Artigos REQUIMTE - Artigos |
Files in This Item:
File | Description | Size | Format | |
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ChemMedChem - 2023 - Silva - Facile Access to Structurally Diverse Antimalarial Indoles Using a One%E2%80%90Pot A3 Coupling and.pdf | 2.11 MB | Adobe PDF |
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