Synthesis, structural features, computational study along with molecular docking examination of organosulfur mercaptoacetic acid based compound

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dc.contributor.authorOsmanova, Sabiya
dc.contributor.authorKurbanova, Malahat
dc.contributor.authorAshfaq, Muhammad
dc.contributor.authorFeizi-Dehnayebi, Mehran
dc.contributor.authorTahir, Muhammad Nawaz
dc.contributor.authorSahin, Onur
dc.date.accessioned2026-04-25T14:19:49Z
dc.date.available2026-04-25T14:19:49Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractWe carried out a thiylating reaction of p-nitroacetophenone with thioglycolic acid. The reaction was carried out in a benzene solution, with a molar ratio of the initial components of 1:4. 1,1-bis-(carboxymethylthio)-1-p-nitrophenylethane (CTNE). Structural features are evaluated via Fourier transform infrared (FT-IR) spectroscopy, 1H NMR and single crystal X-ray diffraction (XRD) analysis. Structure is composed of an organosulfur molecule and a water molecule. Organosulfur molecule adopted non-planar conformation supported via dihedral angle of 71.3 (4)degrees among carboxylic acid groups. Supramolecular organization is primarily supported via O-H & ctdot;O bonding. Further stability of the supramolecular organization is due to pi & ctdot;pi interactions with inter-centroid separation range from 3.85 to 4.01 & Aring;. Strong and weaker interactions are evaluated via Hirshfeld surface analysis which showed that H & ctdot;O contact has highest contribution in stability of the supramolecular organization. DFT calculations at the B3PW91/6-311 + + g (2d,2p) level was employed to optimize the molecular geometry and assess the electronic properties of the synthesized compound. Highest Occupied Molecular Orbital (HOMO)- Lowest Unoccupied Molecular Orbital (LUMO) energy gap (triangle E = 4.06 eV) of the synthesized compound indicates enhanced chemical reactivity and biological potential compared to precursor molecules. Furthermore, molecular docking studies demonstrated a promising binding affinity (-7.05 kcal/mol) toward VEGFR2, stabilized through hydrogen bonding and hydrophobic interactions, suggesting potential anticancer activity through angiogenesis inhibition.
dc.identifier.doi10.1007/s11224-025-02668-3
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.orcid0000-0001-9857-9505
dc.identifier.orcid0000-0002-7868-9085
dc.identifier.orcid0000-0003-4438-4117
dc.identifier.scopus2-s2.0-105022276586
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1007/s11224-025-02668-3
dc.identifier.urihttps://hdl.handle.net/11486/8207
dc.identifier.wosWOS:001615683300001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofStructural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260420
dc.subject1,1-bis-(carboxymethylthio)-1-p-nitrophenylethane
dc.subjectCrystal structure
dc.subjectDFT
dc.subjectMolecular docking
dc.subjectHirshfeld surface analysis
dc.titleSynthesis, structural features, computational study along with molecular docking examination of organosulfur mercaptoacetic acid based compound
dc.typeArticle

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