The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters
| Autor: | Andy G. Harry, Norma O'Donovan, James T. Murphy, Peter T.M. Kenny, Dilip K. Rai, Rachel Tiedt, Áine Mooney, William E. Butler, Mary T. Pryce, Jennifer C. Manton, John Crown, Naomi Walsh |
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| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Dipeptide Chemistry Stereochemistry Hydrochloride Bioorganometallic chemistry Electrospray ionization Organic Chemistry Carbon-13 NMR Biochemistry Amino acid Inorganic Chemistry chemistry.chemical_compound Ferrocene Materials Chemistry Proton NMR Physical and Theoretical Chemistry |
| Zdroj: | Journal of Organometallic Chemistry. 734:86-92 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2012.11.041 |
| Popis: | N -{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2 – 8 were prepared by coupling 6-(ferrocenyl) ethynyl-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(OEt), ProGly(OEt) and ProAla(OEt) using the standard N -(3-dimethylaminopropyl)- N ′-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of 1 H NMR, 13 C NMR, DEPT-135 and 1 H– 13 C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2 – 8 showed micromolar activity in the H1299 NSCLC cell line, with IC 50 values in the range of 3.2–7.2 μM. |
| Databáze: | OpenAIRE |
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