A new family of oxime palladacycles mixed with unsymmetrical phosphorus ylides; synthesis, structural, cytotoxicity and catalytic activity studies
| Autor: | Robert W. Gable, Ahmadreza Shiralinia, Elham Hoveizi, Sepideh Samiee |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Ligand Organic Chemistry Crystal structure 010402 general chemistry Oxime 01 natural sciences Biochemistry Medicinal chemistry Coupling reaction 0104 chemical sciences Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Ylide Materials Chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Phenylboronic acid |
| Zdroj: | Journal of Organometallic Chemistry. 900:120927 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2019.120927 |
| Popis: | In the present investigation, the reactivity of an oxime-derived palladacycle [Pd{C,N–C6H4{C(Me) = NOH}-2}(μ-Cl)]2 toward various unsymmetrical phosphorus ylides has been studied. When the ylide was added to a solution of oxime complex in dichloromethane (2:1 ratio), the new oxime palladacycles of the types [Pd{C,N–C6H4{C(Me) = NOH}-2}(Ph2PCH2PPh2C(H)C(O)C6H4X)]ClO4 (X = Cl (1), Br (2), NO2(3) or OCH3 (4)) were formed by means of bridge-splitting reaction. These are the first description of oxime-based palladacycles mixed with phosphorus ylides. All of complexes were fully characterized by elemental analysis, IR and NMR spectroscopies. The crystal structure of 3 were determined by single-crystal X-ray diffraction analysis that confirmed breaking of Pd–Cl bonds in the initial precursor and allowing phosphorus ylide act as P,C-chelating ligand. In addition, the catalytic activity of 3 was evaluated in the Suzuki cross-coupling reactions of a variety of arylbromides with phenylboronic acid. This complex was also used for the assessment of their anticancer activities against three human carcinoma cell lines: A549 (human lung carcinoma), HT29 (human colon carcinoma), and HeLa (human cervical carcinoma). The results show that the new family of oxime-derived palladacycles could be introduced as promising innovative anticancer complexes and considered as an efficient catalyst in the cross coupling reactions. |
| Databáze: | OpenAIRE |
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