Synthesis, odor characteristics and biological evaluation of N-substituted pyrrolyl chalcones. Issue 44 (31st October 2022)

• Record Type: Journal Article
• Authors: Hu, Jingyi; Ji, Xiaoming; Su, Fangyao; Zhao, Qianrui; Zhang, Ganlin; Zhao, Mingqin; Lai, Miao
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 44(2022)
• Page Start: 8747
• Page End: 8755
• Publication Date: 2022-10-31
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01561g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Base-mediated transition-metal free α-functionalization of N -substituted acetylpyrroles with commercial alcohols to generate various pyrrolyl chalcones is reported, and several prominent bioactive and flavor molecules were obtained. Abstract : 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-1 H -pyrrol-2-yl)prop-2-en-1-one (3j ), ( E )-1-(1-ethyl-1 H -pyrrol-2-yl)-3-phenylprop-2-en-1-one (4a ), ( E )-3-(4-bromophenyl)-1-(1-ethyl-1 H -pyrrol-2-yl)prop-2-en-1-one (4e ), ( E )-3-(4-chlorophenyl)-1-(1-ethyl-1 H -pyrrol-2-yl)prop-2-en-1-one (4f ) and ( E )-1-(1-ethyl-1 H -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.