학술논문
Synthesis, characterisation and biological evaluation of N-(ferrocenyl)naphthoyl amino acid esters as anticancer agentsCCDC reference numbers 718596and 775339. For crystallographic data in CIF or other electronic format see DOI: 10.1039/c0dt00377h.
Document Type
Article
Author
Source
Subject
*ORGANIC synthesis
*AMINO acids
*ANTINEOPLASTIC agents
*X-ray crystallography
*CELL lines
*SPECTRUM analysis
*GABA
*MELANOMA
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Language
ISSN
1477-9226
Abstract
A series of N-(ferrocenyl)naphthoyl amino acid esters 5–18has been prepared by coupling ferrocenyl naphthoic acids 3–4to α-amino acids and linear amino acids in the presence of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) and 1-hydroxybenzotriazole (HOBt). The compounds were fully characterised by a range of NMR spectroscopic techniques, UV-Vis spectroscopy, mass spectrometry and cyclic voltammetry. X-ray crystallographic studies of the intermediate compounds 1–2were also performed. Biological evaluation of the intermediates 1–2and N-(ferrocenyl)naphthoyl amino acid esters 5–18was performed in the H1299 non-small cell lung cancer (NSCLC) cell line and the Sk-Mel-28 metastatic melanoma cell line. The intermediates 1–2failed to produce an effect in either cell line. Compounds 5–18exhibited a strong anti-proliferative effect in the H1299 cell line, whilst the Sk-Mel-28 cells were slightly more resistant to these compounds. N-(6-ferrocenyl-2-naphthoyl)-γ-aminobutyric acid ethyl ester 17shows a particularly high activity in both the H1299 cell line (IC50= 0.62 ± 0.07 μM) and the Sk-Mel-28 cell line (IC50= 1.41 ± 0.04 μM). [ABSTRACT FROM AUTHOR]