title: Design, Synthesis, and Structure--Activity Relationship of New 2-Aryl-3,4-dihydro-β-carbolin-2-ium Salts as Antifungal Agents.
abstract: Twenty-two 2-aryl-9-methyl-3,4-dihydro-β-carbolin-2-ium bromides along with four 9-demethylated derivatives were synthesized and characterized by spectroscopic analysis. By using the mycelium growth rate method, the compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi, and structure-activity relationships (SAR) were derived. Almost all of the compounds showed obvious inhibition activity on each of the fungi at 150 μM. For all of the fungi, 10 of the compounds showed average inhibition rates of >80% at 150 μM, and most of their EC50 values were in the range of 2.0-30.0 μM. SAR analysis showed that the substitution pattern of the N-aryl ring significantly influences the activity; N9-alkylation improves the activity, whereas aromatization of ring-C reduces the activity. It was concluded that the present research provided a series of new 2-aryl-9-alkyl-3,4-dihydro-β-carbolin-2-iums with excellent antifungal potency and structure optimization design for the development of new carboline antifungal agents.
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Hou
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Li-Fei
authors.initials: LF
authors.lastname: Zhu
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Xin-chi
authors.initials: XC
authors.lastname: Yu
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Ma-Qiang
authors.initials: MQ
authors.lastname: Sun
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Fang
authors.initials: F
authors.lastname: Miao
authors.affiliation: College of Science and ‡College of Life Science, Northwest A&F University , Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Le
authors.initials: L
authors.lastname: Zhou
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010935:Plant Diseases / Q000382:microbiology; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D005659:Fungicides, Industrial
keywords: 2-aryl-3,4-dihydro-β-carbolin-2-ium salts; antifungal activity; phytopathogenic fungi; structure−activity relationship; β-carboline compounds