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Title: Synthesis and structure-activity relationships of new chiral spiro-β-lactams highly active against HIV-1 and Plasmodium
Authors: Alves, Nuno Guerreiro 
Bártolo, Inês
Alves, Américo J. S. 
Fontinha, Diana
Francisco, Denise
Lopes, Susana M. M.
Soares, Maria I. L. 
Simões, Carlos J. V. 
Prudêncio, Miguel 
Taveira, Nuno
Pinho e Melo, Teresa M. V. D. 
Keywords: 1,3-Dipolar cycloaddition; 2-Butynoates; Allenes; Anti-HIV agents; Antiplasmodial agents; Phosphane-catalyzed [3+2] annulations; Spiro-3H-pyrazole-β-lactams; Spiro-penicillanates; Spirocyclic compounds; Spirocyclopentenyl-β-lactams; β-Lactams
Issue Date: 5-Jul-2021
Publisher: Elsevier
Project: The authors thank Coimbra Chemistry Centre (CQC), supported by the Portuguese Agency for Scientific Research, “Fundaç~ao para a Ci^encia e a Tecnologia” (FCT) through project UIDB/00313/2020 and UIDP/00313/2020, co-funded by COMPETE2020-UE. iMed. ULisboa, Faculdade de Farm acia de Lisboa, Portugal, is supported by FCT through Projects UIDB/04138/2020 and UIDP/04138/2020, cofunded by COMPETE2020-UE. Miguel Prud^encio acknowledges FCT for grant PTDC/SAU-INF/29550/2017. Nuno Guerreiro Alves and Am erico J. S. Alves thank FCT for fellowships PD/BD/135287/2017 and SFRH/BD/128910/2017, respectively. 
Serial title, monograph or event: European Journal of Medicinal Chemistry
Volume: 219
Abstract: The synthesis and antimicrobial activity of new spiro-β-lactams is reported. The design of the new molecules was based on the structural modulation of two previously identified lead spiro-penicillanates with dual activity against HIV and Plasmodium. The spiro-β-lactams synthesized were assayed for their in vitro activity against HIV-1, providing relevant structure-activity relationship information. Among the tested compounds, two spirocyclopentenyl-β-lactams were identified as having remarkable nanomolar activity against HIV-1. Additionally, the same molecules showed promising antiplasmodial activity, inhibiting both the hepatic and blood stages of Plasmodium infection.
ISSN: 02235234
DOI: 10.1016/j.ejmech.2021.113439
Rights: embargoedAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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