Synthesis and in vitro antifungal activity of new Michael-type amino derivatives of xanthatin, a natural sesquiterpene lactone from Xanthium strumarium L. was written by Zhi, Xiao-yan;Song, Li-li;Liang, Jing;Wei, Si-qi;Li, Yang;Zhang, Yuan;Hao, Xiao-juan;Cao, Hui;Yang, Chun. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2022.Recommanded Product: 2-Methoxyethylamine The following contents are mentioned in the article:
Structural optimization using plant secondary metabolites as templates is one of the important approach to discover pesticide mols. with novel skeletons. Xanthatin, a natural sesquiterpene lactone isolated from the Xanthium plants (Family: Compositae), exhibits important biol. properties. In this work, a series of Michael-type amino derivatives were prepared from xanthatin and their structures were characterized by 1H NMR, 13C NMR and HR-MS, and their antifungal activities against several phytopathogenic fungi were evaluated according to the spore germination method and mycelium growth rate method in vitro. The results illustrated that compounds I (IC50 = 78.91μg/mL) and II (IC50 = 64.51μg/mL) exhibited more promising inhibition activity against spores of F. solani than precursor xanthatin, three compounds exhibited remarkable antifungal effect on C. mandshurica with the average inhibition rates (AIRs) >90%, whereas the AIR of xanthatin was only 59.34%. Meanwhile, the preliminary structure-activity relationships suggested that the amino containing 2-methoxyethyl or 4-chlorophenylmethyl group appended in the C-13 position of xanthatin could yield potential compounds against fungal spores, and the exocyclic double bond of xanthatin is essential to maintain its mycelial growth inhibitory activity. Therefore, the aforementioned findings indicate that partial xanthatin amino-derivatives could be considered for further exploration as the potential lead structures toward development of the new environmentally friendly fungicidal candidates for sustainable crop protection. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Recommanded Product: 2-Methoxyethylamine).
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