Synthesis, Biological Activity and Structure-Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

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dc.contributor.authorAtahan, Alparslan
dc.contributor.authorGençer, Nahit
dc.contributor.authorBilen, Çiğdem
dc.contributor.authorYavuz, Emre
dc.contributor.authorGenç, Hayriye
dc.contributor.authorSönmez, Fatih
dc.contributor.authorKüçükislamoğlu, Mustafa
dc.date.accessioned2020-04-30T23:32:28Z
dc.date.available2020-04-30T23:32:28Z
dc.date.issued2018
dc.departmentDÜ, Teknoloji Fakültesi, Polimer Mühendisliği Bölümüen_US
dc.descriptionGencer, Nahit/0000-0001-7092-8857;en_US
dc.descriptionWOS: 000422674700030en_US
dc.description.abstractA series of novel tetrahydroquinoline derivatives containing urea moiety was synthesized and their invitro inhibitory effects on the human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were evaluated by using the CO2 hydration method. All the synthesized compounds exhibited inhibitory activity against both hCA I and hCA II with 1-(4-fluorophenyl)-3-(4-(4-p-tolyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)urea (7k, IC50 value of 5.28M and 5.51M, against hCA I and hCA II, respectively) as the strongest inhibitor in this study. Structure-activity relationships were also investigated. The results showed that most of synthesized compounds have a higher inhibitory activity against hCA I than hCA II. Also the substituents, containing two or more pairs of non-bonding electrons, generally increased the hCA I and II inhibitory activity. Furthermore, some electronic parameters such as the highest occupied molecular orbital and the lowest unoccupied molecular orbital (HOMO-LUMO) energy levels, electron affinity, total energy and dipole moments of the best inhibitors (7b, 7h and 7k) in this study were also calculated by using Gaussian software. The results revealed that HOMO-LUMO energy differences, total energy, chemical hardness and dipole moment of 7b, 7h and 7k showed a linear relationship with increasing inhibitory activity.en_US
dc.description.sponsorshipGaziosmanpasa University Scientific Research ProjectGaziosmanpasa University [2011/34]en_US
dc.description.sponsorshipThis work was supported by Gaziosmanpasa University Scientific Research Project (Project No: 2011/34).en_US
dc.identifier.doi10.1002/slct.201702562en_US
dc.identifier.endpage534en_US
dc.identifier.issn2365-6549
dc.identifier.issue2en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage529en_US
dc.identifier.urihttps://doi.org/10.1002/slct.201702562
dc.identifier.urihttps://hdl.handle.net/20.500.12684/4729
dc.identifier.volume3en_US
dc.identifier.wosWOS:000422674700030en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofChemistryselecten_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectCarbonic anhydraseen_US
dc.subjectenzyme inhibitionen_US
dc.subjecttetrahydroquinolineen_US
dc.subjectureaen_US
dc.titleSynthesis, Biological Activity and Structure-Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitorsen_US
dc.typeArticleen_US

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