title: Synthesis, bioactivity and structure-activity relationships of new 2-aryl-8-OR-3,4-dihydroisoquinolin-2-iums salts as potential antifungal agents.
abstract: As our continuing research on antifungal dihydroisoquinolin-2-ium salts, forty 2-aryl-8-OR-3,4-dihydroisoquinolin-2-ium bromides were synthesized and characterized by spectroscopic analysis. By using the mycelium growth rate method, the compounds were evaluated for antifungal activity against three plant pathogenic fungi and structure-activity relationships (SAR) were derived. The vast majority of the compounds displayed the medium to high activity with inhibition rates of 50-100% at 150μM. About half of the compounds were more active than their natural model compounds sanguinarine and chelerythrine for all the fungi, and part or most of them were more active than positive drugs thiabendazole and azoxystrobin. SAR analysis showed that both substitution patterns of the C-ring and the type of 8-OR group significantly influenced the activity. Thus, a series of new title compounds with excellent antifungal potency emerged.
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
authors.forename: Li-Fei
authors.initials: LF
authors.lastname: Zhu
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Hou
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
authors.forename: Kun
authors.initials: K
authors.lastname: Zhou
authors.affiliation: College of Life Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
authors.forename: Zong-Bo
authors.initials: ZB
authors.lastname: Tong
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Kuang
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China. Electronic address: genghuiling5@163.com.
authors.forename: Hui-Ling
authors.initials: HL
authors.lastname: Geng
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China. Electronic address: zhoulechem@nwsuaf.edu.cn.
authors.forename: Le
authors.initials: L
authors.lastname: Zhou
mesh_terms: D053119:Benzophenanthridines / Q000737:chemistry / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007546:Isoquinolines / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010935:Plant Diseases / Q000382:microbiology*; D013329:Structure-Activity Relationship; D013827:Thiabendazole / Q000494:pharmacology
chemical_list: D053119:Benzophenanthridines; D005659:Fungicides, Industrial; D007546:Isoquinolines; C005705:sanguinarine; C016299:chelerythrine; D013827:Thiabendazole
keywords: 2-Aryl-8-methoxy-3,4-dihydroisoquinolin-2-ium; Antifungal activity; Isoquinoline; Plant pathogenic fungi; Structure–activity relationship