Chromane derivatives of small aromatic molecules: Chemoenzymatic synthesis and growth inhibitory activity on human tumor cell line LoVo WT
| Autor: | Alessandra Bonamore, Eugenio Lendaro, Alessandra Comandini, Antonio Carraturo, R.M. Matarese, Alberto Macone, Irene Rovardi |
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| Rok vydání: | 2009 |
| Předmět: |
Allylic rearrangement
growth inhibitory activity Double bond Stereochemistry Clinical Biochemistry Prenyltransferase Substituent aromatic prenyl transferase chromane Pharmaceutical Science Antineoplastic Agents Biochemistry Chemical synthesis chemistry.chemical_compound Cell Line Tumor Drug Discovery Humans Moiety Phenols Chromans Molecular Biology chemistry.chemical_classification Organic Chemistry Dimethylallyltranstransferase Growth Inhibitors Recombinant Proteins chemistry Colonic Neoplasms Biocatalysis Molecular Medicine Chromane |
| Zdroj: | Bioorganic & Medicinal Chemistry. 17:6003-6007 |
| ISSN: | 0968-0896 |
| Popis: | Aromatic substrates tyrosol ( p -hydroxyphenylethanol) and 2,6-dihydroxynaphthalene (2,6-DHN) were converted into chromane derivatives by means of chemoenzymatic reactions catalyzed by the aromatic prenyltransferase of bacterial origin NovQ, using dimethylallyl bromide as allylic substrate instead of the natural isoprenyl pyrophosphate substrate. Stereoselective prenylation occurred in o -position with respect to the phenol hydroxyl in both compounds. Prenylated derivatives were readily converted into chromane products via a selective 6- endo -trig cyclization involving the oxygen atom from the phenol moiety and the double bond of the prenyl substituent, a process catalyzed by FeCl 3 . These findings set up the basis of a most convenient two-step, one-pot process which allows for easy recovery of the chromane products in high yields. The chromane derivatives thus obtained were tested for cytotoxicity and pro-apoptotic activity using LoVo WT cells, a line of human colon adenocarcinoma. |
| Databáze: | OpenAIRE |
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