Alkenylation of ortho-palladated phenylglycine: synthesis of stilbene derivatives and 3-aryl-isoquinoline-1-carboxylates

Laga, Eduardo; Cativiela, Carlos; Urriolabeitia, Esteban P.

doi:10.1016/j.jorganchem.2020.121482

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Transition Metal-catalyzed Synthesis Of Stilbene Derivatives1

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Cited by 2 publications

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“…Cross-coupling reaction between organic compounds in the presence of transition metal catalysts is considered a beneficial and versatile approach towards the construction of stilbene derivatives. 22 Synthesis of stilbene-based compounds 1c via cross-coupling reaction between vinylic ethers 1a and aryl Grignard reagents 1b was developed by Iwasaki and co-workers (Scheme 2). 23 The reaction proceeded through selective cleavage of vinylic C–O bond of aryl ether or aryl sulfonate followed by C–C bond formation.…”

Section: Transition Metal-catalyzed Synthesis Of Stilbene Derivativesmentioning

confidence: 99%

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

et al. 2023

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Section: Transition Metal-catalyzed Synthesis Of Stilbene Derivativesmentioning

confidence: 99%

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

et al. 2023

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Mixed N‐heterocyclic carbene and benzyl‐, phenethyl‐, and biphenylamine coordinated Pd complexes: Anticancer activities and stereo‐electronic effects

Teng,

Song,

Chen

et al. 2024

Applied Organom Chemis

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A series of mixed N‐heterocylic carbene (NHC) palladium complexes bearing C^N bidentate ligands derived from benzylamine, phenethylamine, and biphenylamine were prepared and fully characterized by NMR spectroscopy, ESI‐MS spectrometry, and X‐ray diffraction analyses. The complexes were potent in inhibiting proliferation of HepG2 and Caco2 cancer cells, and a SAR (structure–activity relationship) study revealed C^N ligands with stronger electron donation and moderate steric hindrance are more cytotoxic. DNA binding study through UV–vis absorption titration indicated that such complexes bound stronger to CT‐DNA molecules with higher binding constants. Additional molecular docking of the best performer suggested a groove binding mode through hydrogen bonding and π‐π stacking interactions. The apoptosis induced by the two best performers of α,α‐dimethylbenzylamine and S‐α‐methylbenzylamine ligated complexes was further analyzed by morphology change, cell cycle distribution, ROS production, and mitochondrial membrane potential studies.

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Alkenylation of ortho-palladated phenylglycine: synthesis of stilbene derivatives and 3-aryl-isoquinoline-1-carboxylates

Cited by 2 publications

References 75 publications

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

Mixed N‐heterocyclic carbene and benzyl‐, phenethyl‐, and biphenylamine coordinated Pd complexes: Anticancer activities and stereo‐electronic effects

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