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Molecules 2017, 22(8), 1345; doi:10.3390/molecules22081345

Inhibitors of the Detoxifying Enzyme of the Phytoalexin Brassinin Based on Quinoline and Isoquinoline Scaffolds

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada
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Received: 17 July 2017 / Accepted: 8 August 2017 / Published: 14 August 2017
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Abstract

The detoxification of the phytoalexin brassinin to indole-3-carboxaldehyde and S-methyl dithiocarbamate is catalyzed by brassinin oxidase (BOLm), an inducible fungal enzyme produced by the plant pathogen Leptosphaeria maculans. Twenty-six substituted quinolines and isoquinolines are synthesized and evaluated for antifungal activity against L. maculans and inhibition of BOLm. Eleven compounds that inhibit BOLm activity are reported, of which 3-ethyl-6-phenylquinoline displays the highest inhibitory effect. In general, substituted 3-phenylquinolines show significantly higher inhibitory activities than the corresponding 2-phenylquinolines. Overall, these results indicate that the quinoline scaffold is a good lead to design paldoxins (phytoalexin detoxification inhibitors) that inhibit the detoxification of brassinin by L. maculans. View Full-Text
Keywords: antifungal; brassinin oxidase; camalexin; crucifer; Leptosphaeria maculans; paldoxin; phenylquinoline; phytoalexin detoxification antifungal; brassinin oxidase; camalexin; crucifer; Leptosphaeria maculans; paldoxin; phenylquinoline; phytoalexin detoxification
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MDPI and ACS Style

Pedras, M.S.C.; Abdoli, A.; Sarma-Mamillapalle, V.K. Inhibitors of the Detoxifying Enzyme of the Phytoalexin Brassinin Based on Quinoline and Isoquinoline Scaffolds. Molecules 2017, 22, 1345.

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