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

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2024-05-20 DOI:10.1080/00397911.2024.2356641

Abraão Pinheiro de Sousa , Helivaldo Diógenes da Silva Souza , Alexandre Almeida-Júnior , Marcelo Felipe Rodrigues da Silva , Laísa Vilar Cordeiro , Edeltrudes de Oliveira Lima , Gabriela Fehn Fiss , Petrônio Filgueiras de Athayde-Filho

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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, λ_max were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high ε_max 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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从 4-羟基查耳酮中提取的新型酯类是具有抗菌作用的潜在防晒剂

我们有策略地合成了十种新型 4-酯查耳酮（甘草查耳酮类似物），以研究芳基烯酮分子中的电奉献或电撤回取代基对其药理和光保护特性的影响。对 4-查耳酮的类药物特性进行了评估，结果表明其具有开发新型候选药物的积极特性。在体外抗菌评价中，异戊烯基 4-酯查尔酮对金黄色葡萄球菌、白色念珠菌和热带念珠菌菌株具有活性，最低抑菌浓度（MIC）在 2.64-3.32 µmol mL-1 之间，异丁酰基 4-酯查尔酮 5d（4'-Br）对所有测试菌株都具有抗菌活性，最低抑菌浓度为 2.74 µmol mL-1。在紫外可见光研究中，λmax 主要出现在 312-327 纳米的紫外线波段。SPF-UVB 的最佳值在 18.04 到 21.06 之间，εmax 值很高，这表明 4-酯查尔酮具有作为防晒剂的潜力。此外，卤代化合物对盐蒿有轻微毒性，这也是一个环境问题。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.