Strychnos alkaloids: total synthesis, characterization, DFT investigations, and molecular docking with AChE, BuChE, and HSA

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dc.authoriduludag, Nesimi/0000-0002-2819-3612
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorÜstun, Elvan
dc.contributor.authorSerdaroğlu, Goncagül
dc.date.accessioned2023-05-06T17:20:48Z
dc.date.available2023-05-06T17:20:48Z
dc.date.issued2022
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractAn efficient five steps, the protection-deprotection synthetic a novel synthetic routes to(+/-) noruleine (f)-uleine, are reported starting from tetrahydrocarbazole fused monoalkyl nitrile at C-2 position that is prepared on mul-tigram scale from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetonitrile (1) as well as the key azocino [4,3-b]indole skeleton is constructed via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tet-rahydrocarbazole derivative possessing direct amide synthesis from nitrile. As a result, Total synthesis of nor-uleine and uleine has been developed, which is accomplished in 4 and 5-steps synthesis of the ABCD tetracyclic of the strychnos alkaloids with an overall yield of 44% and 39%, respectively. The DFT computations were per-formed with B3LYP/6-311g(d,p) level to determine inter and intramolecular interactions and reactivity features of the compound 3-6. Also, TD-DFT computations were performed to characterize the electronic absorption spectra of all compounds. Last, the interactions of compounds 3-6 with selected targets AChE, BuChE, and HSA were evaluated in light of the molecular dockings. The bioactivity and drug-likeness scores revealed that com-pound 6 3-6 can be proper candidate for future drug-design studies more than the other compounds.
dc.description.sponsorshipScientific and Technological Research Council of Turkey [TUBITAK] [112T503]
dc.description.sponsorshipNesimi Uludag was supported by Scientific and Technological Research Council of Turkey [TUBITAK Project No.112T503] .
dc.identifier.doi10.1016/j.heliyon.2022.e11990
dc.identifier.issn2405-8440
dc.identifier.issue12en_US
dc.identifier.pmid36531635
dc.identifier.scopus2-s2.0-85144046729
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.heliyon.2022.e11990
dc.identifier.urihttps://hdl.handle.net/20.500.11776/11954
dc.identifier.volume8
dc.identifier.wosWOS:000904031300016
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherElsevier Sci Ltd
dc.relation.ispartofHeliyon
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectUleine
dc.subjectNoruleine
dc.subjectAlzheimer's disease
dc.subjectDFT computations
dc.subjectMolecular dockings
dc.subjectConcise Total-Synthesis
dc.subjectReductive Cyclization Route
dc.subjectHuman Serum-Albumin
dc.subjectFt-Ir
dc.subjectCrystal-Structure
dc.subjectOrbital Methods
dc.subjectAb-Initio
dc.subjectBasis-Set
dc.subjectDrug
dc.subjectFramework
dc.titleStrychnos alkaloids: total synthesis, characterization, DFT investigations, and molecular docking with AChE, BuChE, and HSA
dc.typeArticle

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