Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties

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Özet

Indole has been known as a key heterocyclic motif in the development of new structures for both chemical and biological properties. In this current study, a new range of indole-7-carbohydrazides has been successfully synthesized starting from the readily available 3-phenyl and 2,3-diphenyl 4,6-dimethoxyindoles. The structures of the novel compounds were confirmed by utilizing 1H NMR, 13C NMR, FT-IR, high-resolution mass spectrometry, and single crystal X- ray diffraction techniques. In addition, the indole-7-carbohydrazides showed promising antioxidant results in preliminary screens. Some of the new compounds generated from dimethoxy indoles were also screened for their anticancer activity against SH-SHY5Y (human neuroblastoma), AGS (human gastric adenocarcinoma), and MDA-MB-231 (human breast adenocarcinoma) cell lines. The results revealed that the compound 12 was the promising candidate, showing cytotoxic effects on both neuroblastoma, stomach, and breast cancer cells.

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https://rdlopen.rawdatalibrary.net/r/bayburt/11835Resmi atıflarda kullanılan kalıcı adres
DOI
https://doi.org/10.1002/jhet.4562Yayıncı resmi DOI adresi
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorKandemir, Hakan
dc.contributor.authorİzgi, Samet
dc.contributor.authorCınar, Irfan
dc.contributor.authorCebeci, Fatma
dc.contributor.authorDirican, Ebubekir
dc.contributor.authorSaglam, Mehmet F.
dc.contributor.authorSengul, Ibrahim F.
dc.date.accessioned2026-10-29T19:08:51.347599383Z
dc.date.available2026-10-29T19:08:51.347599383Z
dc.date.issued2023
dc.description.abstractIndole has been known as a key heterocyclic motif in the development of new structures for both chemical and biological properties. In this current study, a new range of indole-7-carbohydrazides has been successfully synthesized starting from the readily available 3-phenyl and 2,3-diphenyl 4,6-dimethoxyindoles. The structures of the novel compounds were confirmed by utilizing 1H NMR, 13C NMR, FT-IR, high-resolution mass spectrometry, and single crystal X- ray diffraction techniques. In addition, the indole-7-carbohydrazides showed promising antioxidant results in preliminary screens. Some of the new compounds generated from dimethoxy indoles were also screened for their anticancer activity against SH-SHY5Y (human neuroblastoma), AGS (human gastric adenocarcinoma), and MDA-MB-231 (human breast adenocarcinoma) cell lines. The results revealed that the compound 12 was the promising candidate, showing cytotoxic effects on both neuroblastoma, stomach, and breast cancer cells.
dc.description.sponsorshipTürkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK, (120Z116)
dc.description.sponsorshipTürkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK
dc.description.sponsorshipTekirdağ Namık Kemal Üniversitesi, TNKU, (19.220, NKUBAP.01)
dc.description.sponsorshipTekirdağ Namık Kemal Üniversitesi, TNKU
dc.identifier.doi10.1002/jhet.4562
dc.identifier.eissn1943-5193
dc.identifier.endpage85
dc.identifier.issn0022-152X
dc.identifier.issue1
dc.identifier.scopus2-s2.0-85137568357
dc.identifier.startpage74
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/11835
dc.identifier.volume60
dc.identifier.wosWOS:000852569600001
dc.language.isoen
dc.publisherHeteroCorporation
dc.relation.ispartofJournal of Heterocyclic Chemistry
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject.classificationChemistry, Organic
dc.subject.classificationChemistry
dc.subject.other2 3 diphenyl indole
dc.subject.other2 3 phenyl dimethoxyindole derivative
dc.subject.other3 diphenyl 4 6 dimethoxyindole derivative
dc.subject.other3 phenyl indole
dc.subject.other7 (hydrazonomethyl) 4 6 dimethoxy 2 3 diphenyl 1h indole
dc.subject.other7 (hydrazonomethyl) 4 6 dimethoxy 3 phenyl 1h indole
dc.subject.otherhydrazide derivative
dc.subject.otherindole 7 carbohydrazide derivative
dc.subject.otherindole derivative
dc.subject.otherindometacin
dc.subject.othermelatonin
dc.subject.othern ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 3 (trifluoromethyl)benzohydrazide
dc.subject.othern ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 4 methylbenzohydrazide
dc.subject.othern ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 4 nitrobenzohydrazide
dc.subject.othern ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene)acetohydrazide
dc.subject.othern ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene)benzohydrazide
dc.subject.othern ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene) 3 (trifluoromethyl)benzohydrazide
dc.subject.othern ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene) 4 nitrobenzohydrazide
dc.subject.othern ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene)acetohydrazide
dc.subject.otheroxypertine
dc.subject.otherunclassified drug
dc.subject.otherABTS radical scavenging assay
dc.subject.otherantineoplastic activity
dc.subject.otherantioxidant activity
dc.subject.otherArticle
dc.subject.otherbreast adenocarcinoma cell line
dc.subject.othercarbon nuclear magnetic resonance
dc.subject.othercell proliferation
dc.subject.othercell viability
dc.subject.othercontrolled study
dc.subject.othercytotoxicity
dc.subject.otherDPPH radical scavenging assay
dc.subject.otherdrug synthesis
dc.subject.otherfemale
dc.subject.otherFourier transform infrared spectroscopy
dc.subject.othergastric adenocarcinoma cell line
dc.subject.otherhuman
dc.subject.othermass spectrometry
dc.subject.otherneuroblastoma cell line
dc.subject.otherproton nuclear magnetic resonance
dc.subject.otherX ray diffraction
dc.titleMethoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties
dc.typeArticle
rdl.citation.openalex6
rdl.citation.scopus4
rdl.citation.wos4
rdl.oa.statusclosed
rdl.scopus.quartileQ3
rdl.sdgSDG03
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)
rdl.wos.indexIndex Chemicus (IC)