Synthesis, odor characteristics and biological evaluation of N-substituted pyrrolyl chalcones.

A novel approach for converting N-substituted acetylpyrroles and primary alcohols into N-substituted pyrrolyl chalcones in air with the assistance of t-BuOK is reported, and several prominent flavor and bioactive molecules were obtained. The process entails oxidizing the alcohols to the corresponding aldehydes, and t-BuOK is crucial to the effective production of CC bonds by aldol condensation. Gas chromatography-mass spectrometry-olfactometry (GC-MS-O) was used to examine the odor properties of pyrrolyl chalcones, which are usually different from those of the associated acetylpyrroles and alcohols. The biological evaluation assay showed that the products (E)-3-(3-fluorophenyl)-1-(1-methyl-1H-pyrrol-2-yl)prop-2-en-1-one (3j), (E)-1-(1-ethyl-1H-pyrrol-2-yl)-3-phenylprop-2-en-1-one (4a), (E)-3-(4-bromophenyl)-1-(1-ethyl-1H-pyrrol-2-yl)prop-2-en-1-one (4e), (E)-3-(4-chlorophenyl)-1-(1-ethyl-1H-pyrrol-2-yl)prop-2-en-1-one (4f) and (E)-1-(1-ethyl-1H-pyrrol-2-yl)-3-(4-fluorophenyl)prop-2-en-1-one (4g) exhibited excellent inhibitory activity against R. solani with EC50 values from 0.0107 to 0.0134 mg mL-1. Molecular docking of 3j with SDH (succinate dehydrogenase) was performed to reveal the binding modes in the active pocket and analyze the interactions between the molecules and the SDH protein. Meanwhile, they have good thermal stability according to the results of thermogravimetry (TG) analysis.

Enzymatic synthesis of pyridine heterocyclic compounds and their thermal stability.

An efficient method was discovered for catalyzing the esterification under air using Novozym 435 to obtain pyridine esters. The following conditions were found to be optimal: 60 mg of Novozyme 435, 5.0 mL of n-hexane, a molar ratio of 2:1 for nicotinic acids (0.4 mmol) to alcohols (0.2 mmol), 0.25 g of molecular sieve 3A, a revolution speed of 150 rpm, a reaction temperature of 50 °C, and reaction time of 48 h. Under nine cycles of Novozym 435, the 80 % yield was consistently obtained. Optimum conditions were used to synthesize 23 pyridine esters, including five novel compounds. Among them, gas chromatography-mass spectrometry-olfactometry (GC-MS-O) showed phenethyl nicotinate (3g), (E)-hex-4-en-1-yl nicotinate (3m), and octyl nicotinate (3n) possessed strong aromas. Thermogravimetric analysis (TG) revealed that the compounds 3g, 3m and 3n exhibited stability at the specified temperature. This finding provides theoretical support for adding pyridine esters fragrance to high-temperature processed food.