The synthesis, structural characterization and in vitro anticancer activity of novel 1-alkyl-1′-N-meta-(ferrocenyl) benzoyl dipeptide esters and novel 1-alkyl-1′-N-ortho-(ferrocenyl) benzoyl dipeptide esters
| Autor: | John Crown, Mary T. Pryce, Jennifer C. Manton, Peter T.M. Kenny, William E. Butler, Andy G. Harry, Dilip K. Rai, Norma O'Donovan |
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| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Dipeptide integumentary system Hydrochloride Stereochemistry organic chemicals Electrospray ionization Bioorganometallic chemistry Organic Chemistry Carbon-13 NMR Biochemistry Inorganic Chemistry chemistry.chemical_compound chemistry Ferrocene Materials Chemistry Proton NMR Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Journal of Organometallic Chemistry. 766:1-12 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2014.04.027 |
| Popis: | 1-Alkyl-1′- N - meta -(ferrocenyl) benzoyl dipeptide esters 7–18 and 1-alkyl-1′- N - ortho -(ferrocenyl) benzoyl dipeptide esters 19–30 were prepared by coupling the alkyl ferrocenyl benzoic acids 1–6 to the dipeptide ethyl esters Gly-Gly(OEt), 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. The alkyl groups employed in the synthesis were methyl, ethyl and propyl. The compounds were characterized using a combination of 1 H NMR, 13 C NMR, DEPT-135 and 1 H- 13 C COSY (HMQC) spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Selected compounds showed micromolar activity in the H1299 NSCLC cell line, with IC 50 values in the range of 2.6–20.1 μM. |
| Databáze: | OpenAIRE |
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