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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 54, 2024 - Issue 12
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Articles

Novel esters derived from 4-hydroxychalcones as potential sunscreens with antimicrobial action

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Pages 973-991 | Received 27 Mar 2024, Published online: 20 May 2024
 

Abstract

Ten novel 4-esterchalcones, licochalcone analogues, were strategically synthesized to study the effect of electro-donating or electro-withdrawing substituents in the aryl enone moiety on their pharmacological and photoprotective properties. 4-Esterchalcones had their drug-like character evaluated, which demonstrated positive characteristics for the development of novel drug candidates. In the in vitro antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of Staphylococcus aureus, Candida albicans and C. tropicalis with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL−1, and the isobutyryl 4-esterchalcone 5d (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL−1. In the UV-Vis study, λmax were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high εmax values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on Artemia salina.

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Funding

This work was supported by the [Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)] under Grant [number 403134/2021-8]; and [Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)]. Fellowships from CNPq (M.F.R.S., L.V.C., E.O.L. and P.F.A.F.) and CAPES (A.P.S. and H.D.S.S.) are also acknowledged.

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