C–H activations on a 1H-1,4-benzodiazepin-2(3H)-one template

“…[104] Reactions employing the iodonium salt only needed palladium acetate as the catalyst, whereas aryl iodides required the addition of stoichiometric quantities of silver acetate. The CÀH activation/arylation method using diaryliodonium salts has also been applied to the arylation of benzodiazepines [106] and in the synthesis of 3-(1-arylmethylene)oxindoles. [107] Sanford and co-workers developed a palladium-catalyzed 2-arylation of indoles using diaryliodonium salts (Scheme 23).…”

Section: Arylation Of Arenesmentioning

confidence: 99%

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009

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The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.

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“…Compounds were dissolved at 5 mg ml-1 in sterile DMSO, and further diluted with the appropriate complete cell culture medium. After 72 h, cell viability was assessed using MTT(Sigma), also following published protocols [20,[72][73][74].…”

Section: Cell Culturementioning

confidence: 99%

“…Nevertheless, a recent breakthrough from Caires et al [18] has shown that a number of C,N-palladacycles were non-cytotoxic anticancer activity, and have notable cathepsin B inhibitory activity with the potential to treat metastatic cancer [19,20]. However, palladacycles are more stable, and, most important, less toxic, suggesting they could have a more specific antitumor activity in vivo [1,[21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

Elgazwy

Shehata²,

Zaki³

et al. 2013

Med chem (Los Angeles)

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The reaction of 2-bromo-3,4,5-trimethoxybenzaldehyde 1 with Pd(dba) 2 ; dba=dibenzylideneacetone) in the presence of a stoichiometric amount of nitrogen donor ligands, such as N,N,N',, 2,2'-bipyridine (bpy) 4,4'-dimethyl-2,2'-bipyridine (dmbpy) and an 1,10-phenanthroline (Phen), should be added to with equimolar ratio in degassed acetone under nitrogen to give mononuclear σ-aryl palladium (II) complexes cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5}BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L 2 =bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d) in good yields 48-65%. The reaction of the synthesized five-membered C,N-palladacycle cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5} BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L=bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d), with an1-naphthylisocyanates (C 10 H 7 -NCO) and an 1-naphthylisothiocyanates (C 10 H 7 -NCS), leads to the formation of novel palladacycle 4a-d and 5a-d, which was characterized in solution by 1 H NMR spectroscopy. The solid products were characterized by satisfactory elemental analysis and spectra studies. All the resulting complexes 3a-d, 4a-d and 5a-d were tested in vitro against a number of cell lines. For example, it inhibited K562 leukaemia cells with an IC 50 value in the range of (3.00 -4.3) µM (1 h exposure) and displayed cathepsin B inhibitory action with an IC 50 value in the range of (0.045-0.055 µM). .

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C–H activations on a 1H-1,4-benzodiazepin-2(3H)-one template

Cited by 34 publications

References 38 publications

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

Diaryliodonium Salts: A Journey from Obscurity to Fame

Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

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