Polysubstituted pyrrolidines linked to 1,2,3-triazoles: Synthesis, crystal structure, DFT studies, acid dissociation constant, drug-likeness, and anti-proliferative activity

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dc.authoridNural, Yahya/0000-0002-5986-8248
dc.authoridSERTTAS, RIZA/0000-0002-7493-0388
dc.authoridSeferoglu, Nurgul/0000-0001-9368-3354
dc.authoridince, tuncay/0000-0002-5150-3463
dc.authorwosidNural, Yahya/K-1798-2015
dc.authorwosidince, tuncay/Y-7206-2018
dc.authorwosidSERTTAS, RIZA/AAG-7463-2020
dc.contributor.authorInce, Tuncay
dc.contributor.authorSerttas, Riza
dc.contributor.authorDemir, Bunyamin
dc.contributor.authorAtabey, Hasan
dc.contributor.authorSeferoglu, Nurgul
dc.contributor.authorErdogan, Suat
dc.contributor.authorSahin, Ertan
dc.date.accessioned2024-06-12T11:16:41Z
dc.date.available2024-06-12T11:16:41Z
dc.date.issued2020
dc.departmentTrakya Üniversitesien_US
dc.description.abstractNovel pyrrolidines linked to 1,2,3-triazole derivatives, dimethyl 1-(2 (4-R-1H 1,2,3 triazol-1-yl)-acetyl)-5,5-diphenylpyrrolidine-2,4-dicarboxylate, were synthesized in the presence of sodium ascorbate and copper (II) sulfate pentahydrate by click chemistry in excellent 89-95% yield. The H-1 NMR, C-13 NMR, DEPT, COSY, HMQC, FT-IR, HRMS and elemental analysis techniques were used for structural characterization. A single crystal X-ray diffraction study was performed in order to determine the stereochemistry of the compounds. The optimization geometry of the compounds was obtained by performing density functional theory. However, the global reactivity parameters were estimated from frontier molecular orbitals. The calculated global reactivity parameters showed that the most reactive compound was 4e and the least reactive compounds were 4a, 4c and 4d. The acid dissociation constants were determined using potentiometric titration in 20% (v/v) dimethyl sulfoxide-water hydro-organic solvent at 25 +/- 0.1 degrees C, and four dissociation constants relating nitrogen atoms were obtained for each ligand. Six synthesized compounds were screened for their in vitro anti-proliferative activities against human prostate cancer cells, all of which significantly reduced cell proliferation. One of the compounds 4d showed much more anti-proliferative potential relative to the others, delaying the cells at the DNA synthesis phase. The drug-likeness model score (DLS) calculations for all the synthesized compounds using MolSoft websites supported the experimental results of anti-proliferative bioactivity study, and 4d was found to be maximum DLS value of 1.01. (C) 2020 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipMersin University Research Fund [BAP 2019-1-AP4-3292]en_US
dc.description.sponsorshipThis work was funded by Mersin University Research Fund (Project No: BAP 2019-1-AP4-3292). The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).en_US
dc.identifier.doi10.1016/j.molstruc.2020.128400
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85084499747en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2020.128400
dc.identifier.urihttps://hdl.handle.net/20.500.14551/24401
dc.identifier.volume1217en_US
dc.identifier.wosWOS:000546638700001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal Of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectTriazoleen_US
dc.subjectPyrrolidineen_US
dc.subjectClick Chemistryen_US
dc.subjectAcid Dissociation Constanten_US
dc.subjectAnticancer Activityen_US
dc.subjectDFTen_US
dc.subjectStem-Cell Survivalen_US
dc.subjectBiological Evaluationen_US
dc.subjectProstate-Canceren_US
dc.subjectAntimicrobial Activityen_US
dc.subjectMolecular-Structureen_US
dc.subjectClick Chemistryen_US
dc.subjectAnticanceren_US
dc.subjectDerivativesen_US
dc.subjectInhibitionen_US
dc.subjectDiscoveryen_US
dc.titlePolysubstituted pyrrolidines linked to 1,2,3-triazoles: Synthesis, crystal structure, DFT studies, acid dissociation constant, drug-likeness, and anti-proliferative activityen_US
dc.typeArticleen_US

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