title: Synthesis and fungicidal activity of tryptophan analogues - the unexpected calycanthaceous alkaloid derivatives.
abstract: A series of 21 N-protected tryptophan derivatives were synthesised from tryptophan in good yields. Their structures were characterised by IR,1H NMR,13C NMR, DEPT (90° and 135°) and MS analysis. The synthesised compounds were evaluated against a wide variety of plant pathogen fungi. Compounds a19 and a21 displayed activity against Fusarium oxysporum (F. oxysporum), and compound a21 showed high activity against F. oxysporum and Eggplant Verticillium, with EC50values of 58.27 and 77.39 μg mL-1, respectively. Considering that the bioassay of the title compounds was evaluated, effects of the chain alkyl substituents may contribute to the significant variations in fungicidal potency. Their structure-antifungal activity relationships were also discussed. These results will pave the way for further design, structural modification and development of calycanthaceous alkaloids as antimicrobial agents.
authors.affiliation: a School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang , P.R. China.|d Collaborative Innovation Center of Ship Technology in Jiangsu Colleges and Universities/Marine Equipment and Technology Institute for Jiangsu University of Science and Technology , Zhenjiang , P.R. China.
authors.forename: Shaojun
authors.initials: S
authors.lastname: Zheng
authors.affiliation: a School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang , P.R. China.
authors.forename: Yongdong
authors.initials: Y
authors.lastname: Gu
authors.affiliation: c Key Laboratory of Botanical Pesticide R & D in Shaanxi Province , Yangling , P.R. China.
authors.forename: Longbo
authors.initials: L
authors.lastname: Li
authors.affiliation: a School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang , P.R. China.
authors.forename: Rui
authors.initials: R
authors.lastname: Zhu
authors.affiliation: a School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang , P.R. China.
authors.forename: Xingwei
authors.initials: X
authors.lastname: Cai
authors.affiliation: b Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences , Tarim University , Alar , P.R. China.
authors.forename: Hongjin
authors.initials: H
authors.lastname: Bai
authors.affiliation: c Key Laboratory of Botanical Pesticide R & D in Shaanxi Province , Yangling , P.R. China.
authors.forename: Jiwen
authors.initials: J
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D009287:Naphthyridines / Q000737:chemistry* / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology; D013172:Spores, Fungal / Q000187:drug effects; D013329:Structure-Activity Relationship; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D020172:Verticillium / Q000187:drug effects
chemical_list: D000470:Alkaloids; D000935:Antifungal Agents; D009287:Naphthyridines; D014364:Tryptophan; C070236:calycanthine
keywords: Calycanthaceous alkaloids; agrochemicals; fungicidal activity; synthesis; tryptophan