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Synthesis and biological activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles

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dc.contributor.authorKAYMAKÇIOĞLU, BEDİA
dc.contributor.authorsKocyigit-Kaymakcioglu, Bedia; Oruc-Emre, Emine Elcin; Unsalan, Seda; Tabanca, Nurhayat; Khan, Shabana Iqrar; Wedge, David Earl; Iscan, Gokalp; Demirci, Fatih; Rollas, Sevim
dc.date.accessioned2022-03-12T18:07:24Z
dc.date.available2022-03-12T18:07:24Z
dc.date.issued2012
dc.description.abstractVarious 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles (11-20) were prepared by the reaction of aryl substituted hydrazones of 4-fluorobenzoic acid hydrazide (1-10) with acetic anhydride. The structures of the synthesized compounds 11-20, were confirmed by UV, IR, H-1-NMR and mass spectroscopic methods. Antifungal evaluation of the hydrazide-hydrazones 1-10 and corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles 11-20, against clinical and standard Candida pathogens have been performed by using agar diffusion to indentify the active compounds, which were later subjected to a broth microdilution assay to justify the activity level in terms of minimum inhibitory concentrations (MIC). 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide, showed the highest inhibitory activity against Candida albicans (MIC: 125 mu g/ml), and when compared with ketoconazole. In addition, bioauthographic antifungal activity against plant pathogenic fungi such as Colletotrichum, Botrytis, Fusarium, and Phomopsis was conducted. 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide was the most active analog against P. viticola with 91% inhibition at 30 mu M after 144 h. Furthermore, known and the newly synthesized compounds were also screened through a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. 3-Acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole, showed a strong inhibition of NF-kappa B-dependent transcription in SW1353 cells with IC50 value of 0.75 mu g/ml. 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide, and 3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole on intracellular ROS generation in PMA induced HL-60 cells demonstrated potent activity with IC50 values of 0.9 mu g/ml. A strong inhibition of the activity of iNOS activity in LPS induced RAW 264.7 cells was observed for 3-acetyl-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole with IC50 value of 0.3 mu g/ml.
dc.identifier.doi10.1007/s00044-011-9882-z
dc.identifier.eissn1554-8120
dc.identifier.issn1054-2523
dc.identifier.urihttps://hdl.handle.net/11424/231012
dc.identifier.wosWOS:000309348600020
dc.language.isoeng
dc.publisherSPRINGER BIRKHAUSER
dc.relation.ispartofMEDICINAL CHEMISTRY RESEARCH
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectHydrazide-hydrazones
dc.subject1,3,4-Oxadiazoles
dc.subjectAnti-inflammatory
dc.subjectCytotoxicity
dc.subjectAntioxidant
dc.subjectAntifungal
dc.subjectANTIMICROBIAL ACTIVITY
dc.titleSynthesis and biological activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles
dc.typearticle
dspace.entity.typePublication
local.avesis.idf74c5ade-e280-4508-b66e-c84e9d24bc59
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.journal.numberofpages10
oaire.citation.endPage3508
oaire.citation.issue11
oaire.citation.startPage3499
oaire.citation.titleMEDICINAL CHEMISTRY RESEARCH
oaire.citation.volume21
relation.isAuthorOfPublication0f8e7ba6-02e7-4232-84bb-31777a356761
relation.isAuthorOfPublication.latestForDiscovery0f8e7ba6-02e7-4232-84bb-31777a356761

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