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Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors

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dc.contributor.authorPingaew R.
dc.contributor.authorPrachayasittikul V.
dc.contributor.authorMandi P.
dc.contributor.authorNantasenamat C.
dc.contributor.authorPrachayasittikul S.
dc.contributor.authorRuchirawat S.
dc.contributor.authorPrachayasittikul V.
dc.date.accessioned2021-04-05T03:26:28Z
dc.date.available2021-04-05T03:26:28Z
dc.date.issued2015
dc.date.issuedBE2558
dc.description.abstractAbstract A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity (IC50 = 1.3-9.4 μM). Interestingly, the meta analog of triazole-benzene-sulfonamide (34) bearing 6,7-dimethoxy substituents on the isoquinoline ring displayed the most potent aromatase inhibitory activity (IC50 = 0.2 μM) without affecting normal cell. Molecular docking of these triazoles against aromatase revealed that the compounds could snugly occupy the active site of the enzyme through hydrophobic, π-π stacking, and hydrogen bonding interactions. The potent compound 34 was able to form hydrogen bonds with Met374 and Ser478 which were suggested to be the essential residues for the promising inhibition. The study provides compound 34 as a potential lead molecule of anti-aromatase agent for further development. © 2015 Elsevier Ltd.
dc.format.mimetypeapplication/pdf
dc.identifier.citationBioorganic and Medicinal Chemistry. Vol 23, No.13 (2015), p.3472-3480
dc.identifier.doi10.1016/j.bmc.2015.04.036
dc.identifier.issn9680896
dc.identifier.other2-s2.0-84937425435
dc.identifier.urihttps://hdl.handle.net/20.500.14740/6253
dc.rights.holderScopus
dc.subject.other1,2,3 triazole derivative
dc.subject.other1,2,3 triazole sulfonamide derivative
dc.subject.other4 [[1 [3 [(3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other4 [[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [3 [(3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.otherAromatase inhibitor
dc.subject.otherCoumarin oxymethyl
dc.subject.otherFunctional group
dc.subject.otherKetoconazole
dc.subject.otherLetrozole
dc.subject.otherNaphthalene oxymethyl
dc.subject.otherPhenoxymethyl
dc.subject.otherPhenyl group
dc.subject.otherSulfonamide
dc.subject.otherSulfonyl group
dc.subject.otherUnclassified drug
dc.subject.otherAntineoplastic agent
dc.subject.otherAromatase
dc.subject.otherAromatase inhibitor
dc.subject.otherCYP19A1 protein, human
dc.subject.otherIsoquinoline derivative
dc.subject.otherProtein binding
dc.subject.otherSulfonamide
dc.subject.otherTriazole derivative
dc.subject.otherAnimal cell
dc.subject.otherArticle
dc.subject.otherBinding affinity
dc.subject.otherBinding site
dc.subject.otherCarbon nuclear magnetic resonance
dc.subject.otherChemical interaction
dc.subject.otherChemical reaction
dc.subject.otherClick reaction
dc.subject.otherConcentration response
dc.subject.otherControlled study
dc.subject.otherDrug cytotoxicity
dc.subject.otherDrug mechanism
dc.subject.otherDrug potency
dc.subject.otherDrug safety
dc.subject.otherDrug screening
dc.subject.otherDrug synthesis
dc.subject.otherEnzyme active site
dc.subject.otherEnzyme inhibition
dc.subject.otherHydrogen bond
dc.subject.otherHydrophobicity
dc.subject.otherIC50
dc.subject.otherMass spectrometry
dc.subject.otherMolecular docking
dc.subject.otherNonhuman
dc.subject.otherPi pi stacking interaction
dc.subject.otherProton nuclear magnetic resonance
dc.subject.otherStructure activity relation
dc.subject.otherVero cell line
dc.subject.otherAnimal
dc.subject.otherCell survival
dc.subject.otherChemical phenomena
dc.subject.otherChemistry
dc.subject.otherChlorocebus aethiops
dc.subject.otherDrug effects
dc.subject.otherHuman
dc.subject.otherSynthesis
dc.subject.otherAnimals
dc.subject.otherAntineoplastic Agents
dc.subject.otherAromatase
dc.subject.otherAromatase Inhibitors
dc.subject.otherCatalytic Domain
dc.subject.otherCell Survival
dc.subject.otherCercopithecus aethiops
dc.subject.otherHumans
dc.subject.otherHydrogen Bonding
dc.subject.otherHydrophobic and Hydrophilic Interactions
dc.subject.otherIsoquinolines
dc.subject.otherMolecular Docking Simulation
dc.subject.otherProtein Binding
dc.subject.otherStructure-Activity Relationship
dc.subject.otherSulfonamides
dc.subject.otherTriazoles
dc.subject.otherVero Cells
dc.titleSynthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
dc.typeArticle
dspace.entity.typePublication
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