Design, synthesis and spectroscopic and structural characterization of novel N-(2-hydroxy-5-methyl-phenyl)-2,3-dimethoxybenzamide: DFT, Hirshfeld surface analysis, antimicrobial activity, molecular docking and toxicology

Basit Öğe Kaydı
dc.authoridAYCAN, TUGBA/0000-0002-5313-7807
dc.authoridVeyisoglu, Aysel/0000-0002-1406-5513
dc.authoridOZTURK, FILIZ/0000-0002-0493-0446
dc.authoridCAKMAK, Sukriye/0000-0002-2221-0098
dc.contributor.authorCakmak, Sukriye
dc.contributor.authorAycan, Tugba
dc.contributor.authorOzturk, Filiz
dc.contributor.authorVeyisoglu, Aysel
dc.date.accessioned2025-03-23T19:32:12Z
dc.date.available2025-03-23T19:32:12Z
dc.date.issued2022
dc.departmentSinop Üniversitesi
dc.description.abstractThe novel compound N-(2-hydroxy-5-methylphenyl)-2,3-dimethoxybenzamide, C16H17NO4, I, was prepared by a two-step reaction and then characterized by elemental analysis and X-ray diffraction (XRD) methods. Moreover, its spectroscopic properties were investigated by FT-IR and H-1 and C-13 NMR. Compound I crystallized in the monoclinic space group P2(1)/c and the molecular geometry is not planar, being divided into three planar regions. Supramolecular structures are formed by connecting units via hydrogen bonds. The ground-state molecular structure of I was optimized by the DFT-B3LYP/6-31G(d,p) method and the theoretical structure was compared with that obtained by X-ray diffraction. Intermolecular interactions in the crystal network were studied by two-dimensional (2D) and three-dimensional (3D) Hirshfeld analyses. The calculated electronic transition results were examined and the molecular electrostatic potentials (MEPs) were also determined. The in vitro antimicrobial activities of I against three Gram-positive bacteria, three Gram-negative bacteria and two fungi were determined. The compound was compared with several control drugs and showed better activity than the amoxicillin standard against Gram-positive bacteria B. subtilis, S. aureus and E. faecalis, and Gramnegative bacteria E. coli, K. pneumoniae and P. aeruginosa. The density functional theory (DFT)-optimized structure of the small molecule was used to perform molecular docking studies with proteins from experimentally studied bacterial and fungal organisms using AutoDock to determine the most preferred binding mode of the ligand within the protein cavity. A druglikeness assay and ADME (absorption, distribution, metabolism and excretion) and toxicology studies were carried out and predict a good drug-like character.
dc.identifier.doi10.1107/S2053229622008257
dc.identifier.endpage+
dc.identifier.issn2053-2296
dc.identifier.pmid36063377
dc.identifier.scopus2-s2.0-85137158240
dc.identifier.scopusqualityN/A
dc.identifier.startpage493
dc.identifier.urihttps://doi.org/10.1107/S2053229622008257
dc.identifier.urihttps://hdl.handle.net/11486/5441
dc.identifier.volume78
dc.identifier.wosWOS:000852661700005
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherInt Union Crystallography
dc.relation.ispartofActa Crystallographica Section C-Structural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectcrystal structure
dc.subjectbenzamide
dc.subjectX-ray diffraction
dc.subjectantimicrobial activity
dc.subjectspectroscopic studies
dc.subjectmolecular docking
dc.subjectHirshfeld analysis
dc.titleDesign, synthesis and spectroscopic and structural characterization of novel N-(2-hydroxy-5-methyl-phenyl)-2,3-dimethoxybenzamide: DFT, Hirshfeld surface analysis, antimicrobial activity, molecular docking and toxicology
dc.typeArticle

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
PubMed İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu