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Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1- yl)-N-phenethylbenzenesulfonamides

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dc.contributor.authorPingaew R.
dc.contributor.authorPrachayasittikul S.
dc.contributor.authorRuchirawat S.
dc.contributor.authorPrachayasittikul V.
dc.date.accessioned2021-04-05T03:32:29Z
dc.date.available2021-04-05T03:32:29Z
dc.date.issued2014
dc.date.issuedBE2557
dc.description.abstractA new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N- phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3). Most of the synthesized triazoles 5 displayed cytotoxicity against MOLT-3 cell line, except for analogs 5a-c and 5e. Significantly, 4-phenyltriazoles (5a and 5n), 4-(naphthalen-2-yloxy) methyltriazole 5d, as well as 4-((2-oxo-2H-chromen-7-yl)oxy)methyltriazole 5l showed higher cytotoxic activity against HepG2 cells than the reference drug, etoposide. Interestingly, the 4-phenyltriazole 5a was the most potent and promising compound with IC50 value of 9.07 μM against HepG2 cell line. The analog 5a also exerted the highest cytotoxic activity against HuCCA-1 cells. This finding provides the novel lead molecules for further development. © Springer Science+Business Media 2013.
dc.format.mimetypeapplication/pdf
dc.identifier.citationMedicinal Chemistry Research. Vol 23, No.4 (2014), p.1768-1780
dc.identifier.doi10.1007/s00044-013-0777-z
dc.identifier.issn10542523
dc.identifier.other2-s2.0-84899410430
dc.identifier.urihttps://hdl.handle.net/20.500.14740/6368
dc.rights.holderScopus
dc.subject.other4 [4 [(4 formyl 2 methoxyphenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [(5 formyl 2 methoxyphenoxy)methyl] 1h 1,2,3 triazol y 1l] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [(naphthalen 1 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [(naphthalen 2 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [[(2 oxo 1h chromen 4 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.other4 [4 [[(2 oxo 2h chromen 7 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
dc.subject.otherAntineoplastic agent
dc.subject.otherBenzenesulfonamide derivative
dc.subject.otherEtoposide
dc.subject.otherMethyl 2 [[1 [4 (n phenethylsulfamoyl)phenyl] 1h 1,2,3 triazol 4 yl]methoxy]benzoate
dc.subject.otherN (3,4 dimethoxyphenethyl) 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
dc.subject.otherN (3,4 dimethoxyphenethyl) 4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
dc.subject.otherN (3,4 dimethoxyphenethyl) 4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
dc.subject.otherN phenethyl 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
dc.subject.otherN phenethyl 4 [4 (phenoxymethyl) 1h 1,2,3 triazol 1 yl]benzenesulfonamide
dc.subject.otherN phenethyl 4 [4 [(o tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
dc.subject.otherN phenethyl 4 [4 [(p tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
dc.subject.otherPhenethylamine derivative
dc.subject.otherTriazole derivative
dc.subject.otherUnclassified drug
dc.subject.otherArticle
dc.subject.otherCancer cell culture
dc.subject.otherChemical reaction
dc.subject.otherClick reaction
dc.subject.otherCycloaddition
dc.subject.otherCytotoxicity
dc.subject.otherDrug structure
dc.subject.otherDrug synthesis
dc.subject.otherHuman
dc.subject.otherHuman cell
dc.subject.otherIC 50
dc.subject.otherProton nuclear magnetic resonance
dc.titleSynthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1- yl)-N-phenethylbenzenesulfonamides
dc.typeArticle
dspace.entity.typePublication
swu.datasource.scopushttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84899410430&doi=10.1007%2fs00044-013-0777-z&partnerID=40&md5=28635881403896eb7d621130f3eff0ca

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