The synthesis, structural characterization and in vitro anti-cancer activity of novel 1-alkyl-1′-N-para-(ferrocenyl) benzoyl dipeptide esters
| Autor: | John Crown, William E. Butler, Mary T. Pryce, Dilip K. Rai, Peter T.M. Kenny, Andy G. Harry, Jennifer C. Manton, Norma O'Donovan |
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| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Dipeptide Stereochemistry Hydrochloride Electrospray ionization Bioorganometallic chemistry Organic Chemistry Carbon-13 NMR Biochemistry Inorganic Chemistry chemistry.chemical_compound Ferrocene chemistry Materials Chemistry Proton NMR Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Journal of Organometallic Chemistry. 757:28-35 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2014.01.031 |
| Popis: | 1-Alkyl-1′- N - para -(ferrocenyl) benzoyl dipeptide esters 4 – 12 were prepared by coupling the alkyl ferrocenyl benzoic acids 1 – 3 to the dipeptide ethyl esters Gly- L -Ala(OEt), Gly- L -Leu(OEt) and Gly- L -Phe(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). Selected compounds showed micromolar activity in the H1299 NSCLC cell line, with IC 50 values in the range of 4.5–6.6 μM. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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