Design, synthesis, docking studies and bioactivity evaluation of 1,2,3-triazole eugenol derivatives.

IF 3.2 4区医学 Q3 CHEMISTRY, MEDICINAL Future medicinal chemistry Pub Date : 2024-08-19 DOI:10.1080/17568919.2024.2385292

Thiago Antonio de Sousa Cutrim, Fernando Fontes Barcelos, Leandra Martins Meireles, Poliana Aparecida Rodrigues Gazolla, Ângela Maria Almeida Lima, Róbson Ricardo Teixeira, Luiza Carvalheira Moreira, Vagner Tebaldi de Queiroz, Luiz Cláudio Almeida Barbosa, Pedro Alves Bezerra Morais, Cláudia Jorge do Nascimento, Jochen Junker, Adilson Vidal Costa, Marcio Fronza, Rodrigo Scherer

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Abstract

Aim: The design, synthesis, docking studies and evaluation of the in vitro antifungal and cytotoxic properties of eugenol (EUG) containing 1,2,3-triazole derivatives are reported. Most of the derivatives have not been reported.Materials & methods: The EUG derivatives were synthesized, molecular docked and tested for their antifungal activity.Results: The compounds showed potent antifungal activity against Trichophyton rubrum, associated with dermatophytosis. Compounds 2a and 2i exhibited promising results, with 2a being four-times more potent than EUG. The binding mode prediction was similar to itraconazole in the lanosterol-14-α-demethylase wild-type and G73E mutant binding sites. Additionally, the pharmacokinetic profile prediction suggests good gastrointestinal absorption and potential oral administration.Conclusion: Compound 2a is a promising antifungal agent against dermatophytosis caused by T. rubrum.

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1,2,3-三唑丁香酚衍生物的设计、合成、对接研究和生物活性评估。

目的：报告了含丁香酚（EUG）的 1,2,3-三唑衍生物的设计、合成、对接研究以及体外抗真菌和细胞毒性特性评估。材料与方法：合成了丁香油酚（EUG）衍生物，并对其进行了分子对接和抗真菌活性测试：结果：这些化合物对与皮肤癣菌病有关的红毛癣菌具有很强的抗真菌活性。化合物 2a 和 2i 表现出良好的效果，其中 2a 的药效是 EUG 的四倍。在羊毛甾醇-14-α-脱甲基酶野生型和 G73E 突变体结合位点的结合模式预测与伊曲康唑相似。此外，药代动力学特征预测表明，该化合物具有良好的胃肠道吸收和口服潜力：结论：化合物 2a 是一种很有前途的抗真菌剂，可防治由红念珠菌引起的皮肤癣菌病。

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来源期刊

Future medicinal chemistry CHEMISTRY, MEDICINAL-

CiteScore

5.80

自引率

2.40%

发文量

118

审稿时长

4-8 weeks

期刊介绍： Future Medicinal Chemistry offers a forum for the rapid publication of original research and critical reviews of the latest milestones in the field. Strong emphasis is placed on ensuring that the journal stimulates awareness of issues that are anticipated to play an increasingly central role in influencing the future direction of pharmaceutical chemistry. Where relevant, contributions are also actively encouraged on areas as diverse as biotechnology, enzymology, green chemistry, genomics, immunology, materials science, neglected diseases and orphan drugs, pharmacogenomics, proteomics and toxicology.