New thiophene derivatives: chemoselective synthesis, antitumor effectiveness, structural characterization, DFT calculations, Hirshfeld surface, and Fukui function analysis

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dc.authoridhttps://orcid.org/0000-0003-4492-2181
dc.contributor.authorBin Muhsinah, Abdullatif
dc.contributor.authorAlharbi, Mohammed M.
dc.contributor.authorKheder, Nabila Abdelshafy
dc.contributor.authorSoliman, Saied M.
dc.contributor.authorGhabbour, Hazem A.
dc.contributor.authorMahmoud, Naglaa S.
dc.contributor.authorElhaty, Ismail A. M.
dc.contributor.authorMabkhot, Yahia N.
dc.date.accessioned2025-05-27T12:06:33Z
dc.date.available2025-05-27T12:06:33Z
dc.date.issued2024
dc.departmentSağlık Bilimleri Fakültesi
dc.description.abstractIn this study, the chemoselective synthesis of two new thiophene derivatives is presented. The structure of newly synthesized thiophenes derivatives; ethyl 4-acetyl-3-phenyl-5-(phenylamino)thiophene-2-carboxylate (5) and ethyl (E)-4-(3-(dimethylamino)acryloyl)-3-phenyl-5-(phenylamino)thiophene-2-carboxylate (8) were established using different FTIR and NMR spectral analyses. Compound 8 was isolated as single crystal and its 3D structure was determined using X-ray crystallographic analysis. Possible intermolecular interactions that control the molecular packing of 8 were elucidated using Hirshfeld topology analysis. The O…H (13.7%), H…H (55.3%) and C…C (2.3%) intermolecular interactions are the most significant. Fukui functions showed that C4 in thiophene 5 and C3 in thiophene 8 are the most reactive atoms for nucleophilic attack, while N9 in thiophene 5 and C1 in thiophene 8 are the most reactive atoms for electrophilic attack. Antitumor activity of thiophene 5 was assessed and the results showed higher activity against HepG-2 (7.46 µg/mL) compared to the HCT 116 (12.60 µg/mL) cell line.
dc.identifier.doihttps://doi.org/10.1186/s13065-024-01346-5
dc.identifier.endpage13
dc.identifier.issn2661-801X
dc.identifier.issue1
dc.identifier.startpage1
dc.identifier.urihttps://hdl.handle.net/11363/9833
dc.identifier.volume18
dc.identifier.wos001355102100002
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.institutionauthorElhaty, Ismail A. M.
dc.institutionauthoridhttps://orcid.org/0000-0003-4492-2181
dc.language.isoen
dc.publisherBMC, CAMPUS, 4 CRINAN ST, LONDON N1 9XW, ENGLAND
dc.relation.ispartofBMC CHEMISTRY
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectThiophene
dc.subjectChemoselective synthesis
dc.subjectX-ray crystallography
dc.subjectDFT calculations
dc.subjectHirshfeld surface analysis
dc.subjectFukui function
dc.subjectAntitumor activity
dc.titleNew thiophene derivatives: chemoselective synthesis, antitumor effectiveness, structural characterization, DFT calculations, Hirshfeld surface, and Fukui function analysis
dc.typeArticle

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