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Molecules 2013, 18(9), 10413-10424; doi:10.3390/molecules180910413

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

1
College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China
2
College of Life Science, Northwest A&F University, Yangling 712100, Shaanxi, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 5 July 2013 / Revised: 18 July 2013 / Accepted: 22 August 2013 / Published: 29 August 2013
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Abstract

The title compounds are a class of structurally simple analogues of quaternary benzo[c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenyl ring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 212 exhibited excellent activities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC50 values of 8.88–19.88 µg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha- and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal agrochemicals. Compounds 8 and 2 should have great potential as new broad spectrum antifungal agents for plant protection.
Keywords: 2-aryl-3,4-dihydroisoquinolin-2-ium; antifungal activity; phytopathogenic fungi; structure-activity relationship; sanguinarine; chelerythrine 2-aryl-3,4-dihydroisoquinolin-2-ium; antifungal activity; phytopathogenic fungi; structure-activity relationship; sanguinarine; chelerythrine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Hou, Z.; Yang, R.; Zhang, C.; Zhu, L.-F.; Miao, F.; Yang, X.-J.; Zhou, L. 2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships. Molecules 2013, 18, 10413-10424.

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