Highly selective metal mediated ortho-alkylation of phenol. First platinum containing organometallic chromane analogues
| Autor: | Michele Benedetti, Francesco Capitelli, Francesco Paolo Fanizzi, Sandra Angelica De Pascali, Antonella Ciccarese, Santo Marsigliante, Danilo Migoni, Vita M. Vecchio |
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| Přispěvatelé: | V. M., Vecchio, Benedetti, Michele, Migoni, Danilo, DE PASCALI, SANDRA ANGELICA, Ciccarese, Antonella, Marsigliante, Santo, F., Capitelli, Fanizzi, Francesco Paolo |
| Rok vydání: | 2007 |
| Předmět: |
Models
Molecular Alkylation Stereochemistry Cell Survival chemistry.chemical_element Platinum Compounds Crystallography X-Ray Inorganic Chemistry Metal HeLa chemistry.chemical_compound Electrophilic substitution Organometallic Compounds Phenol Humans Vitamin E Chromans Cytotoxicity biology Molecular Structure TOCOPHEROL TRANSFER PROTEIN FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS VITAMIN-E ALPHA-TOCOPHEROL CRYSTAL-STRUCTURE CYCLOMETALATED COMPLEXES CONJUGATE ADDITION IN-VITRO REACTIVITY CYTOTOXICITY biology.organism_classification chemistry visual_art visual_art.visual_art_medium Chromane Cisplatin Platinum HeLa Cells |
| Zdroj: | Dalton transactions (Cambridge, England : 2003). (48) |
| ISSN: | 1477-9226 |
| Popis: | We were able, for the first time, to synthesize and characterize Pt derivatives with a structural shape similar to vitamin E, having a metalla-chromane core. The formation reaction mechanism includes an unexpected highly selective ortho aromatic electrophilic substitution on phenol, operated by [PtCl(eta(1)-C2H4OR)(N-N)], R = Me or Ph, and a final cyclization step. The X-ray structure of one of the new metalla-chromane complexes [Pt(EtPh)(phen)], 1a, (EtPh = 2-(ethan-2'-yl-kC(1))-1-phenolato-kO(1), phen = 1,10- phenanthroline) is reported. Cytotoxicity and Pt uptake measurements, performed on HeLa cancer cells, show an interesting structure-activity correlation for the new metalla-chromane analogues 1a and [Pt(MeOEtPh)(phen)], 1b, (MeOEtPh = 2-( ethan-2'-yl-kC(1))-4-(methoxy)-1-phenolato- kO(1)), being the structurally closest to vitamin E and also the most active. |
| Databáze: | OpenAIRE |
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