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• In this study, a series of pyrrole-based pharmacologically active heterocyclic compounds (2a-k) were synthesized and characterized by spectral and analytical data. • This assessment focused on their inhibitory potential against acetylcholinesterase and α-glucosidaseenzymes. • The molecular docking, dynamics simulations, and ADME predictions were studied. In this study, pyrrole-based heterocyclic compounds (2a-k) were synthesized and characterized by elemental analysis, IR and NMR spectra. 11 representatives of the pyrrole derivatives were chosen as objects for the studying biological activity. Among them were the ensembles of pyrroles with other pharmacologically active heterocycles, such as pyridines, aminopyrimidines, benzo[b][1,4]diazocin-2(1H)-ones, and fused pyrrole compounds, namely pyrrolo[1′,2′:3,4]imidazo[1,2-a]pyridines. The compounds 2c, 2e, and 2k were synthesized for the first time in this study. This assessment focused on their inhibitory potential against acetylcholinesterase (AChE) and α-glycosidase (α-Gly) enzymes. Among the studied compounds, 4-[5-(4-fluorophenyl)-1-vinyl-1H-pyrrol-2-yl]-6-phenylpyrimidin-2-amine (2e) and 4-[5-(4-fluorophenyl)-1H-pyrrol-2-yl]-6-phenylpyrimidin-2-amine (2f) emerged as leading candidates, demonstrating potent inhibition against AChE and α-glycosidase enzymes with favorable pharmacokinetic profiles. AChE was most effectively inhibited by compounds of 2f and 2i (Ki : 4.50 ± 0.16 and 6.01 ± 0.15 nM). The results from biological activities, molecular docking, dynamics simulations, and ADME predictions collectively highlight the potential of these compounds to be an inhibitor candidate for AChE and α-Gly. In this study, we have designed and synthesized pyrrole derivatives and characterized by elemental analysis, IR and NMR spectra. The biological activities of the synthesized 11 compounds were evaluated. This assessment focused on their inhibitory potential against acetylcholinesterase (hAChE) and α-glucosidase (αGly) enzymes. Among the studied compounds, 4-[5-(4-fluorophenyl)-1-vinyl-1H-pyrrol-2-yl]-6-phenylpyrimidin-2-amine (2e) and 4-[5-(4-fluorophenyl)-1H-pyrrol-2-yl]-6-phenylpyrimidin-2-amine (2f) emerged as leading candidates, demonstrating potent inhibition against hAChE and α-glucosidase enzymes with favorable pharmacokinetic profiles. The results from biological activities, molecular docking, dynamics simulations, and ADME predictions collectively highlight the potential of these compounds to be an inhibitor candidate for hAChE and α-Gly. [Display omitted] [ABSTRACT FROM AUTHOR]

2-(Furan-2-yl)- and 2-(thiophen-2-yl)pyrroles are readily ethynylated with acylbromoacetylenes in the solid Al 2 O 3 medium (no solvent, room temperature, 1 h) to afford 5-(furan-2-yl)- and 5-(thiophen-2-yl)-2-acylethynylpyrroles in 39–74% yields. In the case of 2-(furan-2-yl)pyrroles, an alternative ethynylation of the furan ring takes place, the ratio of the furan and pyrrole ring ethynylation products being 1:5–7. No ethynylation of the thiophene ring as well as ethynylation of both heterocycles in a one molecule has been detected. Thus the reactivity of the heterocycles towards the ethynylation system (acylbromoacetylenes/Al 2 O 3 ) falls in the order: pyrrole>furan>thiophene. [ABSTRACT FROM AUTHOR]

Abstract: Functionalized pyrrolic enols, 2-(2,2-dicyano-1-hydroxyethenyl)-1-methylpyrroles, synthesized from 2-ethenylpyrroles by a nucleophilic SEt-OH exchange, upon heating (75–142°C) are readily rearranged to their 3-isomers in near to quantitative yield. The inter or intramolecular auto-protonation of a pyrrole ring by the acidic enol hydroxyl to form a mesomeric pyrrolium cation or zwitterion is suggested to be a key step in the rearrangement. [Copyright &y& Elsevier]

Simple grinding of the title substrates with Al2O3 results in highly selective ethynylation of the pyrrole rings. [ABSTRACT FROM AUTHOR]