dc.contributor.author | Uludağ, Nesimi | |
dc.contributor.author | Üstun, Elvan | |
dc.contributor.author | Serdaroğlu, Goncagül | |
dc.date.accessioned | 2023-05-06T17:20:48Z | |
dc.date.available | 2023-05-06T17:20:48Z | |
dc.date.issued | 2022 | |
dc.identifier.issn | 2405-8440 | |
dc.identifier.uri | https://doi.org/10.1016/j.heliyon.2022.e11990 | |
dc.identifier.uri | https://hdl.handle.net/20.500.11776/11954 | |
dc.description.abstract | An 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. | en_US |
dc.description.sponsorship | Scientific and Technological Research Council of Turkey [TUBITAK] [112T503] | en_US |
dc.description.sponsorship | Nesimi Uludag was supported by Scientific and Technological Research Council of Turkey [TUBITAK Project No.112T503] . | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Elsevier Sci Ltd | en_US |
dc.identifier.doi | 10.1016/j.heliyon.2022.e11990 | |
dc.rights | info:eu-repo/semantics/openAccess | en_US |
dc.subject | Uleine | en_US |
dc.subject | Noruleine | en_US |
dc.subject | Alzheimer's disease | en_US |
dc.subject | DFT computations | en_US |
dc.subject | Molecular dockings | en_US |
dc.subject | Concise Total-Synthesis | en_US |
dc.subject | Reductive Cyclization Route | en_US |
dc.subject | Human Serum-Albumin | en_US |
dc.subject | Ft-Ir | en_US |
dc.subject | Crystal-Structure | en_US |
dc.subject | Orbital Methods | en_US |
dc.subject | Ab-Initio | en_US |
dc.subject | Basis-Set | en_US |
dc.subject | Drug | en_US |
dc.subject | Framework | en_US |
dc.title | Strychnos alkaloids: total synthesis, characterization, DFT investigations, and molecular docking with AChE, BuChE, and HSA | en_US |
dc.type | article | en_US |
dc.relation.ispartof | Heliyon | en_US |
dc.department | Fakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü | en_US |
dc.authorid | uludag, Nesimi/0000-0002-2819-3612 | |
dc.identifier.volume | 8 | en_US |
dc.identifier.issue | 12 | en_US |
dc.institutionauthor | Uludağ, Nesimi | |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.identifier.wos | WOS:000904031300016 | en_US |
dc.identifier.scopus | 2-s2.0-85144046729 | en_US |
dc.identifier.pmid | 36531635 | en_US |