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
{"title":"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","authors":"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","doi":"10.1080/00397911.2024.2356641","DOIUrl":null,"url":null,"abstract":"<div><p>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 <em>in vitro</em> antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of <em>Staphylococcus aureus</em>, <em>Candida albicans</em> and <em>C. tropicalis</em> with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL<sup>−1</sup>, and the isobutyryl 4-esterchalcone <strong>5d</strong> (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL<sup>−1</sup>. In the UV-Vis study, <em>λ</em><sub>max</sub> were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high <em>ε</em><sub>max</sub> values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on <em>Artemia salina</em>.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Novel esters derived from 4-hydroxychalcones as potential sunscreens with antimicrobial action\",\"authors\":\"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\",\"doi\":\"10.1080/00397911.2024.2356641\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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 <em>in vitro</em> antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of <em>Staphylococcus aureus</em>, <em>Candida albicans</em> and <em>C. tropicalis</em> with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL<sup>−1</sup>, and the isobutyryl 4-esterchalcone <strong>5d</strong> (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL<sup>−1</sup>. In the UV-Vis study, <em>λ</em><sub>max</sub> were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high <em>ε</em><sub>max</sub> values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on <em>Artemia salina</em>.</p></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-05-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124000420\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000420","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Novel esters derived from 4-hydroxychalcones as potential sunscreens with antimicrobial action
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.
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.