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Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents

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dc.contributor.authorPingaew R.
dc.contributor.authorSaekee A.
dc.contributor.authorMandi P.
dc.contributor.authorNantasenamat C.
dc.contributor.authorPrachayasittikul S.
dc.contributor.authorRuchirawat S.
dc.contributor.authorPrachayasittikul V.
dc.date.accessioned2021-04-05T03:32:26Z
dc.date.available2021-04-05T03:32:26Z
dc.date.issued2014
dc.date.issuedBE2557
dc.description.abstractA new series of chalcone-coumarin derivatives (9-19) linked by the 1,2,3-triazole ring were synthesized through the azide/alkyne dipolar cycloaddition. Hybrid molecules were evaluated for their cytotoxic activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) and antimalarial activity toward Plasmodium falciparum. Most of the synthesized hybrids, except for analogs 10 and 16, displayed cytotoxicity against MOLT-3 cell line without affecting normal cells. Analogs (10, 11, 16 and 18) exhibited higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells. Significantly, the high cytotoxic potency of the hybrid 11 was shown to be non-toxic to normal cells. Interestingly, the chalcone-coumarin 18 was the most potent antimalarial compound affording IC50 value of 1.60 μM. Molecular docking suggested that the cytotoxicity of reported hybrids could be possibly due to their dual inhibition of α- and β-tubulins at GTP and colchicine binding sites, respectively. Furthermore, falcipain-2 was identified to be a plausible target site of the hybrids given their antimalarial potency. © 2014 Elsevier Masson SAS. All rights reserved.
dc.format.mimetypeapplication/pdf
dc.identifier.citationEuropean Journal of Medicinal Chemistry. Vol 85, (2014), p.65-76
dc.identifier.doi10.1016/j.ejmech.2014.07.087
dc.identifier.issn2235234
dc.identifier.other2-s2.0-84905161366
dc.identifier.urihttps://hdl.handle.net/20.500.14740/6312
dc.rights.holderมหาวิทยาลัยศรีนครินทรวิโรฒ
dc.subject.other4 ((1 (3 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other4 ((1 (3 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other4 ((1 (3 (3 (3,4 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other4 ((1 (4 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other4 ((1 (4 (3 (3,4,5 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yll)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (3 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (3 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (3 (3 (3,4 dimethoxyphenyl)acryloyl)phenyl) 1 h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (4 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (4 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.other7 ((1 (4 (3 (3,4,5 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one
dc.subject.otherAlpha tubulin
dc.subject.otherAntimalarial agent
dc.subject.otherAntineoplastic agent
dc.subject.otherBeta tubulin
dc.subject.otherChalcone derivative
dc.subject.otherCoumarin derivative
dc.subject.otherEtoposide
dc.subject.otherFalcipain 2
dc.subject.otherUnclassified drug
dc.subject.other1,2,3 triazole derivative
dc.subject.other4 [[1 [3 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other4 [[1 [3 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other4 [[1 [3 [3 (3,4 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other4 [[1 [4 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other4 [[1 [4 [3 (3,4,5 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [3 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [3 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [3 [3 (3,4 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [4 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [4 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.other7 [[1 [4 [3 (3,4,5 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one
dc.subject.otherAntimalarial agent
dc.subject.otherAntineoplastic agent
dc.subject.otherChalcone derivative
dc.subject.otherColchicine
dc.subject.otherCoumarin derivative
dc.subject.otherDihydroartemisinin
dc.subject.otherDoxorubicin
dc.subject.otherEllipticine
dc.subject.otherEtoposide
dc.subject.otherFalcipain 2
dc.subject.otherN [n (3 carboxyoxirane 2 carbonyl)leucyl]agmatine
dc.subject.otherTubulin
dc.subject.otherAntimalarial agent
dc.subject.otherAntineoplastic agent
dc.subject.otherChalcone
dc.subject.otherCoumarin
dc.subject.otherCoumarin derivative
dc.subject.otherCysteine proteinase
dc.subject.otherTriazole derivative
dc.subject.otherAntimalarial activity
dc.subject.otherAntineoplastic activity
dc.subject.otherArticle
dc.subject.otherCancer cell line
dc.subject.otherCarbon nuclear magnetic resonance
dc.subject.otherCycloaddition
dc.subject.otherCytotoxicity
dc.subject.otherDrug structure
dc.subject.otherDrug synthesis
dc.subject.otherHepG2 cell line
dc.subject.otherHuman
dc.subject.otherHuman cell
dc.subject.otherMolecular docking
dc.subject.otherPlasmodium falciparum
dc.subject.otherProton nuclear magnetic resonance
dc.subject.otherA549 cell line
dc.subject.otherAGMK cell line
dc.subject.otherAnimal cell
dc.subject.otherAntimalarial activity
dc.subject.otherArticle
dc.subject.otherCholangiocarcinoma cell line
dc.subject.otherControlled study
dc.subject.otherCrystal structure
dc.subject.otherDrug binding site
dc.subject.otherDrug cytotoxicity
dc.subject.otherDrug potency
dc.subject.otherDrug screening
dc.subject.otherDrug synthesis
dc.subject.otherHydrogen bond
dc.subject.otherIC50
dc.subject.otherLeukemia cell line
dc.subject.otherLymphatic leukemia
dc.subject.otherMolecular docking
dc.subject.otherNonhuman
dc.subject.otherStructure activity relation
dc.subject.otherVero cell line
dc.subject.otherChemistry
dc.subject.otherDrug effects
dc.subject.otherMetabolism
dc.subject.otherProtein conformation
dc.subject.otherSynthesis
dc.subject.otherTumor cell line
dc.subject.otherAntimalarials
dc.subject.otherAntineoplastic Agents
dc.subject.otherCell Line, Tumor
dc.subject.otherChalcone
dc.subject.otherChemistry Techniques, Synthetic
dc.subject.otherCoumarins
dc.subject.otherCysteine Endopeptidases
dc.subject.otherHumans
dc.subject.otherMolecular Docking Simulation
dc.subject.otherPlasmodium falciparum
dc.subject.otherProtein Conformation
dc.subject.otherTriazoles
dc.subject.otherTubulin
dc.titleSynthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents
dc.typeArticle
dspace.entity.typePublication
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