Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies

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dc.authoridTOKALI, Feyzi Sinan/0000-0001-5532-8802
dc.authoridTaslimi, Parham/0000-0002-3171-0633
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.contributor.authorTokali, Feyzi Sinan
dc.contributor.authorTaslimi, Parham
dc.contributor.authorDemirciolu, Ibrahim Hakki
dc.contributor.authorSendil, Kivilcim
dc.contributor.authorTuzun, Burak
dc.contributor.authorGulcin, Ilhami
dc.date.accessioned2024-10-26T18:09:38Z
dc.date.available2024-10-26T18:09:38Z
dc.date.issued2022
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractIn this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against alpha-glycosidase (alpha-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1-3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1-3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward alpha-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 +/- 31.84-904.76 +/- 93.56 nM on AChE and 176.27 +/- 22.87-621.77 +/- 69.98 nM on alpha-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and alpha-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of - 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of - 4.94 against alpha-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.
dc.identifier.doi10.1007/s13738-021-02331-8
dc.identifier.endpage577
dc.identifier.issn1735-207X
dc.identifier.issn1735-2428
dc.identifier.issue2
dc.identifier.scopus2-s2.0-85109259132
dc.identifier.scopusqualityQ3
dc.identifier.startpage563
dc.identifier.urihttps://doi.org/10.1007/s13738-021-02331-8
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30198
dc.identifier.volume19
dc.identifier.wosWOS:000669287400002
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer
dc.relation.ispartofJournal of the Iranian Chemical Society
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectPhenolic Mannich bases
dc.subjectSchiff bases
dc.subjectEnzyme inhibition
dc.subjectMolecular docking
dc.titleNovel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies
dc.typeArticle

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