Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities

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dc.authoridÖkten, Salih/0000-0001-9656-1803
dc.authoridTaslimi, Parham/0000-0002-3171-0633
dc.contributor.authorKocyigit, Ümit Muhammet
dc.contributor.authorÖkten, Salih
dc.contributor.authorÇakmak, Osman
dc.contributor.authorBurhan, Gizem
dc.contributor.authorAtaş, Mehmet
dc.contributor.authorTaslimi, Parham
dc.contributor.authorGülçin, İlhami
dc.date.accessioned2025-01-21T16:35:59Z
dc.date.available2025-01-21T16:35:59Z
dc.date.issued2022
dc.departmentKırıkkale Üniversitesi
dc.description.abstractThe aims of this study are to synthesize and characterize some new phenyl quinoline derivatives and to determine the activities of them and the recently prepared substituted phenyl quinolines against Acetylcholinesterase (AChE) and Charbonic anyhydrase (CA) enzymes and some microorganisms. The 6-phenyl- (3a) and 6,8-diphenyl-(4a) tetrahydroquinolines were prepared by treatment of 6-bromo and 6,8-dibromo-1,2,3,4-tetrahydroquinoline with phenylboronic acids in the presence of Pd catalyze in high yields with respect to our reported procedure. Then, bromination of the 6-phenyl- (3a) and 6,8-diphenyl-(4a) tetrahydroquinolines furnished novel 3-bromo phenyl substituted quinolines 14 and 11 and 8-bromo-6-pheyltetrahydroquinoline (13) in excellent yields (91, 99 and 92 %, respectively). Structures of all prepared compounds were characterized by H-1 NMR,C-13 NMR, FTIR spectroscopy and elemental analysis. Both novel prepared and recent synthesized phenyl substituted tetrahydroquinolines and quinolines were screened for human carbonic anhydrase I, II isoenzymes (hCAs I and II) and AChE inhibitory and antimicrobial activities. Results indicated that all the synthetic compounds exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC50 values. K-i values of novel substituted (trifluoromethoxy, thiomethyl and methoxy) phenyl quinolines 3a-d, 4a-c, 8-12, and 14 for hCA I, hCA II and AChE enzymes were obtained in the ranges 0.31-12.44, 0.92-12.45, and 8.56-27.05 mu M, respectively. Moreover, phenyl quinolines 3a-b, 10, 11, 14 displayed antifungal effect against yeasts in the range of 125-15.62 mu g/mL.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [112T394]; Scientific Research Project Fund of Sivas Cumhuriyet University [ECZ079]
dc.description.sponsorshipThe study was supported by grants from the Scientific and Technological Research Council of Turkey (TUBITAK, Project number: 112T394) and from Scientific Research Project Fund of Sivas Cumhuriyet University, (Grant/Award Numbers: ECZ079).
dc.identifier.doi10.1002/slct.202203469
dc.identifier.issn2365-6549
dc.identifier.issue37
dc.identifier.scopus2-s2.0-85139506086
dc.identifier.scopusqualityQ3
dc.identifier.urihttps://doi.org/10.1002/slct.202203469
dc.identifier.urihttps://hdl.handle.net/20.500.12587/24224
dc.identifier.volume7
dc.identifier.wosWOS:000864002300001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofChemistryselect
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectAcetylcholinesterase; Aryl quinoline and tetrahydroquinoline; Carbonic anhydrase; Enzymes inhibition; Suzuki-Miyura cross-coupling
dc.titleArylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities
dc.typeArticle

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