Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties
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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- WoS
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- OpenAlex
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Tam Kayıt
| Alan | Değer | Dil |
|---|---|---|
| dc.contributor.author | Kandemir, Hakan | |
| dc.contributor.author | İzgi, Samet | |
| dc.contributor.author | Cınar, Irfan | |
| dc.contributor.author | Cebeci, Fatma | |
| dc.contributor.author | Dirican, Ebubekir | |
| dc.contributor.author | Saglam, Mehmet F. | |
| dc.contributor.author | Sengul, Ibrahim F. | |
| dc.date.accessioned | 2026-10-29T19:08:51.347599383Z | |
| dc.date.available | 2026-10-29T19:08:51.347599383Z | |
| dc.date.issued | 2023 | |
| dc.description.abstract | 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. | |
| dc.description.sponsorship | Türkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK, (120Z116) | |
| dc.description.sponsorship | Türkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK | |
| dc.description.sponsorship | Tekirdağ Namık Kemal Üniversitesi, TNKU, (19.220, NKUBAP.01) | |
| dc.description.sponsorship | Tekirdağ Namık Kemal Üniversitesi, TNKU | |
| dc.identifier.doi | 10.1002/jhet.4562 | |
| dc.identifier.eissn | 1943-5193 | |
| dc.identifier.endpage | 85 | |
| dc.identifier.issn | 0022-152X | |
| dc.identifier.issue | 1 | |
| dc.identifier.scopus | 2-s2.0-85137568357 | |
| dc.identifier.startpage | 74 | |
| dc.identifier.uri | https://rdlopen.rawdatalibrary.net/r/bayburt/11835 | |
| dc.identifier.volume | 60 | |
| dc.identifier.wos | WOS:000852569600001 | |
| dc.language.iso | en | |
| dc.publisher | HeteroCorporation | |
| dc.relation.ispartof | Journal of Heterocyclic Chemistry | |
| dc.rights | info:eu-repo/semantics/closedAccess | |
| dc.subject.classification | Chemistry, Organic | |
| dc.subject.classification | Chemistry | |
| dc.subject.other | 2 3 diphenyl indole | |
| dc.subject.other | 2 3 phenyl dimethoxyindole derivative | |
| dc.subject.other | 3 diphenyl 4 6 dimethoxyindole derivative | |
| dc.subject.other | 3 phenyl indole | |
| dc.subject.other | 7 (hydrazonomethyl) 4 6 dimethoxy 2 3 diphenyl 1h indole | |
| dc.subject.other | 7 (hydrazonomethyl) 4 6 dimethoxy 3 phenyl 1h indole | |
| dc.subject.other | hydrazide derivative | |
| dc.subject.other | indole 7 carbohydrazide derivative | |
| dc.subject.other | indole derivative | |
| dc.subject.other | indometacin | |
| dc.subject.other | melatonin | |
| dc.subject.other | n ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 3 (trifluoromethyl)benzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 4 methylbenzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene) 4 nitrobenzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene)acetohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 2 3 diphenyl 1h indol 7 yl]methylene)benzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene) 3 (trifluoromethyl)benzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene) 4 nitrobenzohydrazide | |
| dc.subject.other | n ([4 6 dimethoxy 3 phenyl 1h indol 7 yl]methylene)acetohydrazide | |
| dc.subject.other | oxypertine | |
| dc.subject.other | unclassified drug | |
| dc.subject.other | ABTS radical scavenging assay | |
| dc.subject.other | antineoplastic activity | |
| dc.subject.other | antioxidant activity | |
| dc.subject.other | Article | |
| dc.subject.other | breast adenocarcinoma cell line | |
| dc.subject.other | carbon nuclear magnetic resonance | |
| dc.subject.other | cell proliferation | |
| dc.subject.other | cell viability | |
| dc.subject.other | controlled study | |
| dc.subject.other | cytotoxicity | |
| dc.subject.other | DPPH radical scavenging assay | |
| dc.subject.other | drug synthesis | |
| dc.subject.other | female | |
| dc.subject.other | Fourier transform infrared spectroscopy | |
| dc.subject.other | gastric adenocarcinoma cell line | |
| dc.subject.other | human | |
| dc.subject.other | mass spectrometry | |
| dc.subject.other | neuroblastoma cell line | |
| dc.subject.other | proton nuclear magnetic resonance | |
| dc.subject.other | X ray diffraction | |
| dc.title | Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties | |
| dc.type | Article | |
| rdl.citation.openalex | 6 | |
| rdl.citation.scopus | 4 | |
| rdl.citation.wos | 4 | |
| rdl.oa.status | closed | |
| rdl.scopus.quartile | Q3 | |
| rdl.sdg | SDG03 | |
| rdl.source.index | SCOPUS | |
| rdl.source.index | WOS | |
| rdl.wos.index | Science Citation Index Expanded (SCI-EXPANDED) | |
| rdl.wos.index | Index Chemicus (IC) |

