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Molecules 2016, 21(10), 1349; doi:10.3390/molecules21101349

Synthesis and Antifungal Activity against Fusarium oxysporum of Some Brassinin Analogs Derived from l-tryptophan: A DFT/B3LYP Study on the Reaction Mechanism

Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 49300, Colombia
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Academic Editor: Derek J. McPhee
Received: 14 September 2016 / Revised: 26 September 2016 / Accepted: 8 October 2016 / Published: 11 October 2016
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
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Abstract

An efficient methodology to obtain novel antifungal analogs of brassinin 1 is described. Starting from l-tryptophan 2, N,N′-dialkylthiourea 4, 4-[(1H-indol-3-yl)methylene]-2-sulfanylidene-1,3-thiazolidin-5-one 5 and alkyl (2S)-3-(1H-indol-3-yl)-2-{[(alkylsulfanyl)carbonothioyl]amino}propanoate 6 type 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 intermediate 9. Antifungal activities of all products were then evaluated against Fusarium oxysporum through mycelial growth inhibition using a microscale amended-medium assay. IC50 values were thus determined for each compound. These results showed that 6-related compounds can be considered as promissory antifungal agents. View Full-Text
Keywords: Brassinin; phytoalexin; l-tryptophan derivatives; dithiocarbamate; Fusarium oxysporum Brassinin; phytoalexin; l-tryptophan derivatives; dithiocarbamate; Fusarium oxysporum
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MDPI and ACS Style

Quiroga, D.; Becerra, L.D.; Sadat-Bernal, J.; Vargas, N.; Coy-Barrera, E. Synthesis and Antifungal Activity against Fusarium oxysporum of Some Brassinin Analogs Derived from l-tryptophan: A DFT/B3LYP Study on the Reaction Mechanism. Molecules 2016, 21, 1349.

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