Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives
1
School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China
2
School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, Guangzhou 510006, China
3
Key Laboratory of New Drug Discovery and Evaluation of Ordinary Universities of Guangdong Province, Guangzhou Key Laboratory of Construction and Application of New Drug Screening Model Systems, Guangzhou key Laboratory of Construction and Application of New Drug Screening Model Systems and Guangdong Province Engineering Technology Center for Molecular Probes & Biomedical Imaging, Guangdong Pharmaceutical University, Guangzhou 510006, China
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3116; https://doi.org/10.3390/molecules23123116
Received: 5 November 2018 / Revised: 23 November 2018 / Accepted: 24 November 2018 / Published: 28 November 2018
Pseudoaspidinol is a phloroglucinol derivative with Antifungal activity and is a major active component of Dryopteris fragrans. In our previous work, we studied the total synthesis of pseudoaspidinol belonging to a phloroglucinol derivative and investigated its antifungal activity as well as its intermediates. However, the results showed these compounds have low antifungal activity. In this study, in order to increase antifungal activities of phloroglucinol derivatives, we introduced antifungal pharmacophore allylamine into the methylphloroglucinol. Meanwhile, we remained C1–C4 acyl group in C-6 position of methylphloroglucinol using pseudoaspidinol as the lead compound to obtain novel phloroglucinol derivatives, synthesized 17 compounds, and evaluated antifungal activities on Trichophyton rubrum and Trichophyton mentagrophytes in vitro. Molecular docking verified their ability to combine the protein binding site. The results indicated that most of the compounds had strong antifungal activity, in which compound 17 were found to be the most active on Trichophyton rubrum with Minimum Inhibitory Concentration (MIC) of 3.05 μg/mL and of Trichophyton mentagrophytes with MIC of 5.13 μg/mL. Docking results showed that compounds had a nice combination with the protein binding site. These researches could lay the foundation for developing antifungal agents of clinical value.
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Keywords:
phloroglucinol derivatives; antifungal activity; molecular docking; allylamine; squalene epoxidase
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MDPI and ACS Style
Teng, X.; Wang, Y.; Gu, J.; Shi, P.; Shen, Z.; Ye, L. Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives. Molecules 2018, 23, 3116.
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