Synthesis, characterization, and SAR of arylated indenoquinoline-based cholinesterase and carbonic anhydrase inhibitors

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dc.contributor.authorEkiz, Makbule
dc.contributor.authorTutar, Ahmet
dc.contributor.authorOkten, Salih
dc.contributor.authorButun, Burcu
dc.contributor.authorKocyigit, Umit M.
dc.contributor.authorTaslimi, Parham
dc.contributor.authorTopcu, Guelacti
dc.date.accessioned2020-06-25T18:29:28Z
dc.date.available2020-06-25T18:29:28Z
dc.date.issued2018
dc.departmentKırıkkale Üniversitesi
dc.descriptionOkten, Salih/0000-0001-9656-1803; Topcu, Gulacti/0000-0002-7946-6545
dc.description.abstractWe report the synthesis of bromoindenoquinolines (15a-f) by Friedlander reactions in low yields (13-50%) and the conversion of the corresponding phenyl-substituted indenoquinoline derivatives 16-21 in high yields (80-96%) by Suzuki coupling reactions. To explore the structure-activity relationship (SAR), their inhibition potentials to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase cyctosolic (hCA I and II) enzymes were determined. Monophenyl (16-18) indenoquinolines significantly inhibited the AChE and BChE enzymes in ranges of IC50 37-57nM and 84-93nM, respectively, compared with their starting materials 15a-c and reference compounds (galanthamine and tacrine). On the other hand, these novel arylated indenoquinoline-based derivatives were effective inhibitors of the BChE, hCA I and II, BChE and AChE enzymes with K-i values in the range of 37 +/- 2.04 to 88640 +/- 1990nM for AChE, 120.94 +/- 37.06 to 1150.95 +/- 304.48nM for hCA I, 267.58 +/- 98.05 to 1568.16 +/- 438.67nM for hCA II, and 84 +/- 3.86 to 144120 +/- 2910nM for BChE. As a result, monophenyl indenoquinolines 16-18 may have promising anti-Alzheimer drug potential and 3,8-dibromoindenoquinoline amine (15f) can be novel hCA I and hCA II enzyme inhibitors.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1002/ardp.201800167
dc.identifier.issn0365-6233
dc.identifier.issn1521-4184
dc.identifier.issue9en_US
dc.identifier.pmid30079554
dc.identifier.scopus2-s2.0-85052642498
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1002/ardp.201800167
dc.identifier.urihttps://hdl.handle.net/20.500.12587/7330
dc.identifier.volume351en_US
dc.identifier.wosWOS:000443379600007
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofArchiv Der Pharmazie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectacetylcholinesteraseen_US
dc.subjectbromoindenoquinolinesen_US
dc.subjectbutyrylcholinesteraseen_US
dc.subjectcarbonic anhydraseen_US
dc.subjectenzyme inhibitionen_US
dc.subjectphenyl indenoquinolinesen_US
dc.subjectSARen_US
dc.titleSynthesis, characterization, and SAR of arylated indenoquinoline-based cholinesterase and carbonic anhydrase inhibitorsen_US
dc.typeArticle

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