Semisynthesis and biological evaluation of some novel Mannich base derivatives derived from a natural lignan obovatol as potential antifungal agents.

Semisynthesis and biological evaluation of some novel Mannich base derivatives derived from a natural lignan obovatol as potential antifungal agents. Bioorg Chem. 2019 Nov 23;:103469 Authors: Yang C, Li T, Jiang L, Zhi X, Cao H Abstract Obovatol, a novel lignan isolated from the leaf and stem bark of Magnolia obovata Thunb exhibits many important biological activities. To discover natural-product-based potential fungicides with novel structural skeletons, a series of Mannich base derivatives were prepared by the C-4-aminomethylated modification of obovatol and all synthesized compounds were evaluated for antifungal activities in vitro against several phytopathogenic fungi using the spore germination method and the mycelium growth rate method. Furthermore, their structures were also characterized by 1H NMR, 13C NMR, and HR-MS, and compound 2k was further analyzed by single-crystal X-ray diffraction. Among all of the derivatives, compounds 2b (IC50 = 28.68 µg/mL) and 2g (IC50 = 16.90 µg/mL) demonstrated greater inhibition of Botrytis cinerea spore germination than two positive controls, hymexazol and difenoconazole. Compounds 2c, 2f, and 2g displayed potent mycelial growth inhibition of B. cinerea with an average inhibition rate (AIR) of >90% at a concentration of 100 µg/mL. Additionally, the structure-activity relationships (SARs) suggested that the introduction of a diethylamino, pyrrolyl, 1-methyl-piperazinyl or 1-ethyl...
Source: Bioorganic Chemistry - Category: Chemistry Authors: Tags: Bioorg Chem Source Type: research
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