Publication: Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1- yl)-N-phenethylbenzenesulfonamides
0
0
Issued Date
2014
Resource Type
File Type
application/pdf
ISSN
10542523
Other identifier(s)
2-s2.0-84899410430
Rights Holder(s)
Scopus
Bibliographic Citation
Medicinal Chemistry Research. Vol 23, No.4 (2014), p.1768-1780
Suggested Citation
Pingaew R., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1- yl)-N-phenethylbenzenesulfonamides. Medicinal Chemistry Research. Vol 23, No.4 (2014), p.1768-1780. doi:10.1007/s00044-013-0777-z Retrieved from: https://hdl.handle.net/20.500.14740/6368
Abstract
A 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.
Subject(s)
4 [4 [(4 formyl 2 methoxyphenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(5 formyl 2 methoxyphenoxy)methyl] 1h 1,2,3 triazol y 1l] n phenethylbenzenesulfonamide
4 [4 [(naphthalen 1 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(naphthalen 2 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [[(2 oxo 1h chromen 4 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [[(2 oxo 2h chromen 7 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
Antineoplastic agent
Benzenesulfonamide derivative
Etoposide
Methyl 2 [[1 [4 (n phenethylsulfamoyl)phenyl] 1h 1,2,3 triazol 4 yl]methoxy]benzoate
N (3,4 dimethoxyphenethyl) 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
N (3,4 dimethoxyphenethyl) 4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N (3,4 dimethoxyphenethyl) 4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
N phenethyl 4 [4 (phenoxymethyl) 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 [4 [(o tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 [4 [(p tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
Phenethylamine derivative
Triazole derivative
Unclassified drug
Article
Cancer cell culture
Chemical reaction
Click reaction
Cycloaddition
Cytotoxicity
Drug structure
Drug synthesis
Human
Human cell
IC 50
Proton nuclear magnetic resonance
4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(5 formyl 2 methoxyphenoxy)methyl] 1h 1,2,3 triazol y 1l] n phenethylbenzenesulfonamide
4 [4 [(naphthalen 1 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [(naphthalen 2 yloxy)methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [[(2 oxo 1h chromen 4 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
4 [4 [[(2 oxo 2h chromen 7 yl)oxy]methyl] 1h 1,2,3 triazol 1 yl] n phenethylbenzenesulfonamide
Antineoplastic agent
Benzenesulfonamide derivative
Etoposide
Methyl 2 [[1 [4 (n phenethylsulfamoyl)phenyl] 1h 1,2,3 triazol 4 yl]methoxy]benzoate
N (3,4 dimethoxyphenethyl) 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
N (3,4 dimethoxyphenethyl) 4 [4 [(4 formylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N (3,4 dimethoxyphenethyl) 4 [4 [(4 nitrophenoxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 (4 phenyl 1h 1,2,3 triazol 1 yl)benzenesulfonamide
N phenethyl 4 [4 (phenoxymethyl) 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 [4 [(o tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
N phenethyl 4 [4 [(p tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]benzenesulfonamide
Phenethylamine derivative
Triazole derivative
Unclassified drug
Article
Cancer cell culture
Chemical reaction
Click reaction
Cycloaddition
Cytotoxicity
Drug structure
Drug synthesis
Human
Human cell
IC 50
Proton nuclear magnetic resonance