Synthesis and antibacterial activity of racemic paecilocin A and its derivatives against methicillin-sensitive and -resistant Staphylococcus aureus

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.

Mots clés

Natural phthalide Antibacterial activity Halogen-metal exchange

Domaines

Chimie organique

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S004040392100071X.pdf (204.13 Ko)

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https://hal.inrae.fr/hal-03205212

Soumis le : vendredi 10 mars 2023-09:20:06

Dernière modification le : vendredi 15 mars 2024-22:00:03

Archivage à long terme le : dimanche 11 juin 2023-19:19:50

Dates et versions

hal-03205212 , version 1 (10-03-2023)

Licence

Paternité - Pas d'utilisation commerciale

Identifiants

HAL Id : hal-03205212 , version 1
DOI : 10.1016/j.tetlet.2021.152888
PII : S0040-4039(21)00071-X
WOS : 000626511700033

Citer

Walaa Ibraheem, Quentin Wils, Emilie Camiade, Elhadi Ahmed, Jérôme Thibonnet, et al.. Synthesis and antibacterial activity of racemic paecilocin A and its derivatives against methicillin-sensitive and -resistant Staphylococcus aureus. Tetrahedron Letters, 2021, 67, 4 p. ⟨10.1016/j.tetlet.2021.152888⟩. ⟨hal-03205212⟩

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