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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
Author to whom correspondence should be addressed.
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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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

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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