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Synthesis and In Vitro Antibacterial Activity of Quaternized 10-Methoxycanthin-6-one Derivatives

College of Veterinary Medicine, Northwest A&F University, Yangling 712100, Shaanxi, China
College of Chemistry and Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, China
Authors to whom correspondence should be addressed.
Molecules 2019, 24(8), 1553;
Received: 27 March 2019 / Revised: 16 April 2019 / Accepted: 16 April 2019 / Published: 19 April 2019
(This article belongs to the Section Medicinal Chemistry)
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Background: Based on our previous work, we found that 10-methoxycanthin-6-one displayed potential antibacterial activity and quaternization was an available method for increasing the antibacterial activity. Here, we explored the antibacterial activity of quaternized 10-methoxy canthin-6-one derivatives. Methods and Results: Twenty-two new 3-N-benzylated 10-methoxy canthin-6-ones were designed and synthesized through quaternization reaction. The in vitro antibacterial activity against three bacteria was evaluated by the double dilution method. Moreover, the structure–activity relationships (SARs) were carefully summarized in order to guide the development of antibacterial canthin-6-one agents. Two highly active compounds (6p and 6t) displayed 8-fold superiority (MIC = 3.91 µg/mL) against agricultural pathogenic bacteria R. solanacearum and P. syringae compared to agrochemical streptomycin sulfate, and showed potential activity against B. cereus. Moreover, these two compounds exhibited good “drug-like” properties, low cytotoxicity, and no inhibition on seed germination. Conclusions: This work provides two new effective quaternized canthin-6-one derivatives as candidate bactericide, promoting the development of natural-sourced bactericides and preservatives. View Full-Text
Keywords: 10-methoxycanthin-6-one; quaternization; antibacterial; SARs 10-methoxycanthin-6-one; quaternization; antibacterial; SARs

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Li, N.; Liu, D.; Dai, J.-K.; Wang, J.-Y.; Wang, J.-R. Synthesis and In Vitro Antibacterial Activity of Quaternized 10-Methoxycanthin-6-one Derivatives. Molecules 2019, 24, 1553.

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