Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates

Abstract

A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

“…Pyrrole-based compounds 8i and 10-12 bear the acrylate moiety as another potentially active pharmacophore group, as does pyrrolo[1,2-a]pyrazine 4l, one of the most active derivatives against the six Candida species. Some acrylate-based heterocyclic derivatives have been proposed as antifungals due to their growth inhibition of Aspergillus, Geotrichum, and various other pathogenic plant fungi [58,59].…”

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

“…The potent hybrid 67 showed moderate inhibitory activity against P. theae and P. adianticola on rape plants at 12.5 μg/mL, even though it was much lower than that of carbendazim. 104 Their group prepared another series of βmethoxyacrylate derivatives containing a carboxylate unit afterward. The most promising compound 68 displayed prominent antifungal activity against R. solani with EC 50 value of 0.85 μg/mL, comparable to that of azoxystrobin (EC 50 = 2.28 μg/mL) and significantly better than that of hymexazol (EC 50 = 17.09 μg/mL).…”

“…Bao and co-workers synthesized a series of butenolide–acrylate conjugates. The potent hybrid 67 showed moderate inhibitory activity against P. theae and P. adianticola on rape plants at 12.5 μg/mL, even though it was much lower than that of carbendazim . Their group prepared another series of β-methoxyacrylate derivatives containing a carboxylate unit afterward.…”