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Open AccessArticle

Synthesis and Antimicrobial Evaluation of Side-Chain Derivatives based on Eurotiumide A

1
Graduate School of Pharmaceutical Sciences and Research Cluster on “Innovative Chemical Sensing”, Tokushima University, 1-78-1 Shomachi, Tokushima 770-8505, Japan
2
Department of Microbiology and Infection Control Sciences, Kyoto Pharmaceutical University, Misasaginakauchi-cho, Yamashita-Ku, Kyoto 607-8414, Japan
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2020, 18(2), 92; https://doi.org/10.3390/md18020092
Received: 30 November 2019 / Revised: 24 January 2020 / Accepted: 29 January 2020 / Published: 30 January 2020
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
Side-chain derivatives of eurotiumide A, a dihydroisochroman-type natural product, have been synthesized and their antimicrobial activities described. Sixteen derivatives were synthesized from a key intermediate of the total synthesis of eurotiumide A, and their antimicrobial activities against two Gram-positive bacteria, methicillin-susceptible and methicillin-resistant Staphylococcus aureus (MSSA and MRSA), and a Gram-negative bacterium, Porphyromonas gingivalis, were evaluated. The results showed that derivatives having an iodine atom on their aromatic ring instead of the prenyl moiety displayed better antimicrobial activity than eurotiumide A against MSSA and P. gingivalis. Moreover, we discovered that a derivative with an isopentyl side chain, which is a hydrogenated product of eurotiumide A, is the strongest antimicrobial agent against all three strains, including MRSA. View Full-Text
Keywords: antibiotics; natural product; P. gingivalis; methicillin-resistant S. aureus antibiotics; natural product; P. gingivalis; methicillin-resistant S. aureus
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MDPI and ACS Style

Nakayama, A.; Sato, H.; Nakamura, T.; Hamada, M.; Nagano, S.; Kameyama, S.; Furue, Y.; Hayashi, N.; Kamoshida, G.; Karanjit, S.; Oda, M.; Namba, K. Synthesis and Antimicrobial Evaluation of Side-Chain Derivatives based on Eurotiumide A. Mar. Drugs 2020, 18, 92.

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