Synthesis and antibacterial activity of racemic paecilocin A and its derivatives against methicillin-sensitive and -resistant Staphylococcus aureus
| Autor: | Quentin Wils, Julien Petrignet, Elhadi M. Ahmed, Emilie Camiade, Jérôme Thibonnet, Walaa Ibraheem, Emilie Thiery |
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| Přispěvatelé: | Synthèse et isolement de molécules bio-actives EA 7502 (SIMBA), Université de Tours, Faculty of pharmacy, Gezira, University of Gezira, Infectiologie et Santé Publique (UMR ISP), Université de Tours-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), French Ministry for Research and Innovation, Université de Tours (UT), Université de Tours (UT)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Stereochemistry
010402 general chemistry medicine.disease_cause 01 natural sciences Biochemistry Aldehyde Phthalide chemistry.chemical_compound Drug Discovery medicine Methicillin sensitive chemistry.chemical_classification Strain (chemistry) Natural phthalide 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Natural compound Organic Chemistry Total synthesis biochemical phenomena metabolism and nutrition bacterial infections and mycoses 0104 chemical sciences Halogen-metal exchange Staphylococcus aureus Antibacterial activity |
| Zdroj: | Tetrahedron Letters Tetrahedron Letters, Elsevier, 2021, 67, 4 p. ⟨10.1016/j.tetlet.2021.152888⟩ |
| ISSN: | 0040-4039 |
| Popis: | International audience; A total synthesis in four steps of racemic paecilocin A, a natural marine phthalide is reported. The synthetic pathway includes an iodine-magnesium exchange followed by a condensation on an aldehyde and represents a sufficiently flexible approach to allow the synthesis of twelve analogs. The synthesized compounds were investigated for their antibacterial activity against methicillin-sensitive Staphylococcus aureus (MSSA) and methicillin-resistant strain (MRSA). Three analogs were found to have similar or better antibacterial activity than the natural compound on MRSA. (C) 2021 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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