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Synthesis and characterization of flurbiprofen hydrazide derivatives as potential anti-HCV, anticancer and antimicrobial agents

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dc.contributor.authorTATAR, ESRA
dc.contributor.authorsCikla, Pelin; Tatar, Esra; Kucukguzel, Ilkay; Sahin, Fikrettin; Yurdakul, Dilsad; Basu, Amartya; Krishnan, Ramalingam; Nichols, Daniel Brian; Kaushik-Basu, Neerja; Kucukguzel, S. Guniz
dc.date.accessioned2022-03-12T18:11:09Z
dc.date.available2022-03-12T18:11:09Z
dc.date.issued2013
dc.description.abstractA novel series of new flurbiprofen hydrazide derivatives 2-(2-fluorobiphenyl-4-yl)-N'-[(substituted phenyl/5-nitro-2-furyl)methylene]propanehydrazide (3a-k), 2-(2-fluorobiphenyl-4-yl)-N-(2-substituted-4-oxo-1,3-thiazolidine-3-yl)propanamide (4a-b, 4d-k), 2-[2-(2-fluorobiphenyl-4-yl) propanoyl]-N-substituted hydrazinecarbothioamide (5a-h) and 2-(2-fluorobiphenyl-4-yl)-N'-[(3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]propanehydrazide (6a-b, 6e and 6g) has been synthesized in this study. All synthesized compounds were screened for antimicrobial activity against various bacterial and fungal strains. Additionally, compounds were evaluated for the ability to inhibit Hepatitis C virus NS5B polymerase. The most active 4-thiazolidinone compound was 4k (SGK119) with 67.0 % and thiosemicarbazide compound was 5d (SGK123) with 69.50 % inhibition at 200 mu M against hepatitis C virus NS5B RNA polymerase. Anticancer activity of the selected compounds (3i, 3j, 3h, 4d, 4i and 6b) was determined at a single dose towards the full panel of 60 human cancer cell lines by the National Cancer Institute (NCI). 2-(2-Fluoro-4-biphenylyl)-N-[2-[4-(trifluoromethyl)phenyl]-4-oxo-1,3-thiazolidine-3-yl]propanamide 4d, containing thiazolidinone ring, demonstrated the most marked effect with 20.80 % growth percent on leukaemia cancer cell line SR at 10(-5) M. The results demonstrated that none of the compounds tested have anticandidal and antifungal activities, but two of them (4a and 4i) showed antibacterial inhibition against Micrococcus luteus, and Staphylococcus cohnii and Staphylococcus aureus, respectively.
dc.identifier.doi10.1007/s00044-013-0550-3
dc.identifier.eissn1554-8120
dc.identifier.issn1054-2523
dc.identifier.urihttps://hdl.handle.net/11424/231431
dc.identifier.wosWOS:000325827000005
dc.language.isoeng
dc.publisherSPRINGER BIRKHAUSER
dc.relation.ispartofMEDICINAL CHEMISTRY RESEARCH
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectAnticancer activity
dc.subjectHepatitis C NS5B polymerase
dc.subject4-Thiazolidinone
dc.subjectHydrazide-hydrazone
dc.subjectFlurbiprofen
dc.subjectC VIRUS-INFECTION
dc.subjectNATIONAL-CANCER-INSTITUTE
dc.subjectTUMOR-CELL-LINES
dc.subjectHEPATITIS-C
dc.subjectHEPATOCELLULAR-CARCINOMA
dc.subjectR-FLURBIPROFEN
dc.subjectCYCLOOXYGENASE-2 EXPRESSION
dc.subjectPOLYMERASE INHIBITORS
dc.subjectBIOLOGICAL-ACTIVITIES
dc.subjectANTITUMOR-ACTIVITY
dc.titleSynthesis and characterization of flurbiprofen hydrazide derivatives as potential anti-HCV, anticancer and antimicrobial agents
dc.typearticle
dspace.entity.typePublication
local.avesis.idc4bcc54b-0ba1-4707-9821-b9953a5fc14e
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.journal.numberofpages15
oaire.citation.endPage5699
oaire.citation.issue12
oaire.citation.startPage5685
oaire.citation.titleMEDICINAL CHEMISTRY RESEARCH
oaire.citation.volume22
relation.isAuthorOfPublicatione2c939bf-1387-4174-802c-e714419b20af
relation.isAuthorOfPublication.latestForDiscoverye2c939bf-1387-4174-802c-e714419b20af

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