Synthesis of novel benzofuran-4,7-quinones from 4,6-dimethoxybenzofurans specifically targeting breast and lung cancer cells

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dc.contributor.authorUcar, Tugce N. Uslu
dc.contributor.authorIzgi, Samet
dc.contributor.authorDemir, Elif Ayazoglu
dc.contributor.authorUzuner, Selcen Celik
dc.contributor.authorSengul, Ibrahim F.
dc.contributor.authorUzuner, Ugur
dc.contributor.authorKandemir, Hakan
dc.date.accessioned2025-04-06T12:23:56Z
dc.date.available2025-04-06T12:23:56Z
dc.date.issued2025
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstract4,6-Dimethoxy-2-phenylbenzofurans were synthesized from the one-pot reactions of 3,5-dimethoxyphenol and a range of alpha-bromoacetophenones. The dimethoxybenzofurans were then selectively formylated at C7 using Vilsmeier-Haack method to generate 4,6-dimethoxybenzofuran-7-carbaldehydes which have been effectively converted to 6-dimethoxybenzofuran-4,7-quinones by Dakin oxidation. The cytotoxic potentials of the targeted compounds in MDA-MB-231 breast cancer and A549 lung cancer cell lines were investigated and compared to the cytotoxicity profiles of normal breast and bronchial cells. 2-Phenylbenzofurans mostly targeted lung cancer cells whereas benzofuran-7-carbaldehydes were specifically cytotoxic for metastatic breast cancer cells. The targeted benzofuran derivatives were found to be the most effective compounds for lung and breast cancer. ADME analyses showed lethal doses of all compounds excluding benzofuran-4,7-quinones are around 4000 mg/kg.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [122Z598]; TUBITAK
dc.description.sponsorshipThis study was supported by the Scientific and Technological Research Council of Turkey (TUBITAK) under Grant Number 122Z598. The authors thank TUBITAK for their support. Authors thank Prof Zuelal ATLI SEKEROGLU (Ordu University, Department of Molecular Biology and Genetics, Tuerkiye) for providing a batch of BEAS-2B cells.
dc.identifier.doi10.1007/s00706-025-03304-w
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.scopus2-s2.0-86000732950
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1007/s00706-025-03304-w
dc.identifier.urihttps://hdl.handle.net/20.500.11776/17269
dc.identifier.wosWOS:001441649400001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer Wien
dc.relation.ispartofMonatshefte Fur Chemie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250406
dc.subjectHeterocycles
dc.subjectBenzofuran
dc.subjectCytotoxicity
dc.subjectBioorganic chemistry
dc.subjectDakin oxidation
dc.titleSynthesis of novel benzofuran-4,7-quinones from 4,6-dimethoxybenzofurans specifically targeting breast and lung cancer cells
dc.typeArticle

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