Efficient synthesis of chromeno[2,3-b]pyridine derivatives using Zn(OTf)2 as a catalyst: DFT computations, molecular docking and ADME studies

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dc.authorscopusid36447801100
dc.authorscopusid6507868758
dc.authorscopusid7003702216
dc.contributor.authorSerdaroğlu, G.
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorÜstün, E.
dc.date.accessioned2023-05-06T17:20:48Z
dc.date.available2023-05-06T17:20:48Z
dc.date.issued2023
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractAn efficient method was developed for the synthesis of chromeno[2,3-b]pyridine derivatives by using Zn(OTf)2 (Zinc trifluoromethanesulfonate) via one-pot [3 + 3] cascade annulation methods using 2-amino-4H-chromen-4-one with a different substituted group (1–6) and trans-chalcone. This strategy offers the pharmacological importance of 2-amino-4H-chromen-4-one derivatives in reaction time and good yields. This approach also brings a different perspective to the literature as an intramolecular cyclization pathway. All computational works were performed at the B3LYP/6–311++G** level of theory. After confirming the optimized structures and comparing the calculated spectroscopic data with corresponding experimental data, the intramolecular interactions were evaluated on the basis of NBO “Natural Bond Orbital” theory. The quantum chemical reactivity features and FMO “Frontier Molecular Orbital” analyses were conducted at the same level of theory. The solvent effect on the reactivity behaviors was also investigated by using the results that were determined by obtaining the different solvent environments. Molecular docking was employed to explore the binding affinities of the compounds against AChE (Acetylcholinesterase), BuChE (Butyrylcholinesterase), and HSA (Human serum albümin). Also, the bioavailability and drug-likeness properties of compounds 1–6 were determined to explore the possible usage in further drug design works. © 2023 Elsevier B.V.
dc.description.sponsorshipTürkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK: 112 T503; Tekirdağ Namık Kemal Üniversitesi, TNKU
dc.description.sponsorshipFinancial support for this research from the Scientific and Technological Research Council of Turkey (TUBITAK Project No. 112 T503). The authors thank Namık Kemal University for the analysis of our article structure. All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.description.sponsorshipFinancial support for this research from the Scientific and Technological Research Council of Turkey (TUBITAK Project No. 112 T503). The authors thank Namık Kemal University for the analysis of our article structure. All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1016/j.molliq.2023.121364
dc.identifier.issn0167-7322
dc.identifier.scopus2-s2.0-85147543470
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molliq.2023.121364
dc.identifier.urihttps://hdl.handle.net/20.500.11776/11958
dc.identifier.volume375
dc.identifier.wosWOS:000996221500001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherElsevier B.V.
dc.relation.ispartofJournal of Molecular Liquids
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectChromene
dc.subjectDFT computations
dc.subjectMolecular dockings
dc.subjectNBO analysis
dc.subjectPyridine
dc.subjectBinding energy
dc.subjectBiochemistry
dc.subjectChemical bonds
dc.subjectComputation theory
dc.subjectComputational chemistry
dc.subjectCyclization
dc.subjectDesign for testability
dc.subjectMolecular modeling
dc.subjectMolecular orbitals
dc.subjectSolvents
dc.subjectSynthesis (chemical)
dc.subjectChromenes
dc.subjectDFT computations
dc.subjectEfficient synthesis
dc.subjectMolecular docking
dc.subjectNBO analysis
dc.subjectOne pot
dc.subjectPyridine derivatives
dc.subjectSubstituted groups
dc.subjectTrifluoromethanesulfonate
dc.subject]+ catalyst
dc.subjectPyridine
dc.titleEfficient synthesis of chromeno[2,3-b]pyridine derivatives using Zn(OTf)2 as a catalyst: DFT computations, molecular docking and ADME studies
dc.typeArticle

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