Microwave-assisted synthesis of new sulfonyl hydrazones, screening of biological activities and investigation of structure-activity relationship

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dc.authoridSICAK, Yusuf/0000-0003-2339-5837
dc.authoridoruc-emre, emine elcin/0000-0001-6840-9660
dc.authoridOzturk, Mehmet/0000-0001-8932-4535
dc.contributor.authorKaraman, Nurcan
dc.contributor.authorOruc-Emre, Emine Elcin
dc.contributor.authorSicak, Yusuf
dc.contributor.authorCatikkas, Berna
dc.contributor.authorKarakucuk-Iyidogan, Aysegul
dc.contributor.authorOzturk, Mehmet
dc.date.accessioned2024-09-18T20:54:16Z
dc.date.available2024-09-18T20:54:16Z
dc.date.issued2016
dc.departmentHatay Mustafa Kemal Üniversitesien_US
dc.description.abstractSulfonyl hydrazone scaffold and the piperidine rings have important role in medicinal chemistry. This study shows the synthesis of two novel series of sulfonyl hydrazone having piperidine derivatives by condensing benzene sulfonyl hydrazides with ethyl 4-oxopiperidine-1-carboxylate and 2,6-diphenylpiperidin-4-one. Physical and chemical properties of compounds have been characterized and reported by utilizing their melting point, elemental analysis, IR, H-1-NMR, C-13 NMR, 2D NMR and mass spectra results. Synthesized compounds were evaluated for antioxidant capacity and anticholinesterase activity. The antioxidant capacity of the compounds were screened through four complementary test, i.e., beta-carotene-linoleic acid for lipid peroxidation, DPPH free radical (DPPH center dot), ABTS cation radical (ABTS(+center dot)) and CUPRAC assays. Assay results showed that N'-(2,6-diphenylpiperidin-4-ylidene)-4-bromobenzenesulfonohydrazide (11) has the highest lipid peroxidation inhibitory activity. Within the assay series, N'-(2,6-diphenylpiperidin-4-ylidene)-4-bromobenzenesulfonohydrazide (11) exhibited better activity than standard BHT in DPPH center dot scavenging, while N'-(2,6-diphenylpiperidin-4-ylidene)benzenesulfonohydrazide (10) showed the best ABTS(+center dot) scavenging assay. The CUPRAC assay revealed that ethyl 4-(2-(4-methoxyphenylsulfonyl)hydrazono)piperidine-1-carboxylate (5) indicated the best activity with A (0.50) value among the tested compounds than the antioxidant standard alpha-tocopherol. According to AChE assay, N'-(2,6-diphenylpiperidin-4-ylidene)-4-chlorobenzenesulfonohydrazide (12) had the best activity, while in BChE assay the highest activity was found for compound N'-(2,6-diphenylpiperidin-4-ylidene)-4-methylbenzenesulfonohydrazide (16). Electronic and structural characteristics and density functional studies of the all newly synthesized compounds have been reported for better understanding in molecular-level. NMR, molecular electrostatic potential (MEP), Delta E (HOMO-LUMO) band gap and the dipole moments of the molecules have been also analyzed and reported.en_US
dc.description.sponsorshipResearch Foundation of Gaziantep University [FEF.11.03]en_US
dc.description.sponsorshipThis study was supported by the Research Foundation of Gaziantep University (Project No: FEF.11.03). We would like to thanks the Gazi University for providing Gaussian 09 W software. The numerical calculations reported in this paper were performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA Resources).en_US
dc.identifier.doi10.1007/s00044-016-1592-0
dc.identifier.endpage1607en_US
dc.identifier.issn1054-2523
dc.identifier.issn1554-8120
dc.identifier.issue8en_US
dc.identifier.scopus2-s2.0-84968626534en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.startpage1590en_US
dc.identifier.urihttps://doi.org/10.1007/s00044-016-1592-0
dc.identifier.urihttps://hdl.handle.net/20.500.12483/11717
dc.identifier.volume25en_US
dc.identifier.wosWOS:000381207600007en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Birkhauseren_US
dc.relation.ispartofMedicinal Chemistry Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPiperidineen_US
dc.subjectSulfonyl hydrazoneen_US
dc.subjectAlzheimer'sen_US
dc.subjectAntioxidanten_US
dc.subjectDFT calculationsen_US
dc.titleMicrowave-assisted synthesis of new sulfonyl hydrazones, screening of biological activities and investigation of structure-activity relationshipen_US
dc.typeArticleen_US

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