title: Synthesis and Antifungal Activity against Fusarium oxysporum of Some Brassinin Analogs Derived from l-tryptophan: A DFT/B3LYP Study on the Reaction Mechanism.
abstract: An efficient methodology to obtain novel antifungal analogs of brassinin1is described. Starting from l-tryptophan2,N,N'-dialkylthiourea4, 4-[(1H-indol-3-yl)methylene]-2-sulfanylidene-1,3-thiazolidin-5-one5and alkyl (2S)-3-(1H-indol-3-yl)-2-{[(alkylsulfanyl)carbonothioyl]amino}propanoate6type compounds were obtained as main products in different ratios depending on the reaction conditions via a tandem dithiocarbamate formation and Michael addition reaction. In order to understand the dependence of the reaction conditions on the mechanism pathway, a DFT/B3LYP study was performed. The results suggested the existence of competitive mechanistic routes which involve the presence of an ionic dithiocarbamate intermediate9. Antifungal activities of all products were then evaluated againstFusarium oxysporumthrough mycelial growth inhibition using a microscale amended-medium assay. IC50values were thus determined for each compound. These results showed that6-related compounds can be considered as promissory antifungal agents.
authors.affiliation: Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia. diego.quiroga@unimilitar.edu.co.
authors.forename: Diego
authors.initials: D
authors.lastname: Quiroga
authors.affiliation: Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia. ldbecerrag@unal.edu.co.
authors.forename: Lili Dahiana
authors.initials: LD
authors.lastname: Becerra
authors.affiliation: Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia. john.bernal@unimilitar.edu.co.
authors.forename: John
authors.initials: J
authors.lastname: Sadat-Bernal
authors.affiliation: Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia. u0500887@unimilitar.edu.co.
authors.forename: Nathalia
authors.initials: N
authors.lastname: Vargas
authors.affiliation: Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia. ericsson.coy@unimilitar.edu.co.
authors.forename: Ericsson
authors.initials: E
authors.lastname: Coy-Barrera
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D025282:Mycelium / Q000187:drug effects; D013859:Thiocarbamates / Q000737:chemistry; D014364:Tryptophan / Q000737:chemistry*; D000094162:Phytoalexins
chemical_list: D000935:Antifungal Agents; D007211:Indoles; D013859:Thiocarbamates; D014364:Tryptophan; C089020:brassinin; D000094162:Phytoalexins
keywords: ">l-tryptophan derivatives; Brassinin; Fusarium oxysporum; dithiocarbamate; phytoalexin