title: Structure-activity relationship in the interaction of substituted perinaphthenones with Mycosphaerella fijiensis.
abstract: The levels of native fungitoxic perinaphthenone phytoalexins in susceptible Musa varieties (banana), which are commercially grown in large plantations, are too low to provide plants with long-lasting protection against highly pathogenic fungi. Novel strategies for plant protection are necessary to reduce crop losses and to prevent the development of resistant fungal strains. The synthesis of novel fungicides based on the structures of perinaphthenone natural products is considered to be a promising strategy. Thirteen substituted perinaphthenones, among them two known natural products (1, 2) and 11 synthetics (3-13), were evaluated for their activity against Mycosphaerella fijiensis , and their half-maximal inhibitory concentrations (IC(50)) were calculated to establish structure-activity relationships (SAR). A SAR trend was hypothesized, leading to the design of a new compound, 4-methoxy-2-nitro-1H-phenalen-1-one (14); the new compound displayed significantly enhanced in vitro activity against M. fijiensis compared to other perinaphthenone derivatives. The activity of 14 was comparable to that of two commercial fungicides.
authors.affiliation: Universidad Nacional de Colombia sede Medellín, Autopista Norte, Calle 64 Cra 65, Medellín, Colombia.
authors.forename: William
authors.initials: W
authors.lastname: Hidalgo
authors.forename: Luisa
authors.initials: L
authors.lastname: Duque
authors.forename: Jairo
authors.initials: J
authors.lastname: Saez
authors.forename: Rafael
authors.initials: R
authors.lastname: Arango
authors.forename: Jesús
authors.initials: J
authors.lastname: Gil
authors.forename: Benjamín
authors.initials: B
authors.lastname: Rojano
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
authors.forename: Felipe
authors.initials: F
authors.lastname: Otálvaro
mesh_terms: D001203:Ascomycota / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D043803:Phenalenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology; D013329:Structure-Activity Relationship
chemical_list: D005659:Fungicides, Industrial; D043803:Phenalenes; C038036:phenalen-1-one