TY - JOUR
T1 - The synthesis, structural characterization and biological evaluation of novel N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters as anticancer agents
AU - Harry, Andy G.
AU - Murphy, James P.
AU - O'Donovan, Norma
AU - Crown, John
AU - Rai, Dilip K.
AU - Kenny, Peter T.M.
N1 - Publisher Copyright:
© 2017 Elsevier B.V.
PY - 2017
Y1 - 2017
N2 - A series of N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters 4–18 were prepared by coupling para-(ferrocenyl) ethynyl benzoic acid 3 to the amino acids GABA(OMe), GABA(OEt) and the dipeptide esters GlyGly(OMe), GlyGly(OEt), Gly-L-Ala(OMe), Gly-L-Ala(OEt), Gly-D-Ala(OMe), Gly-D-Ala(OEt), Gly-L-Leu(OEt), Gly-L-Phe(OEt), SarGly(OMe), SarGly(OEt), Sar-L-Ala(OEt), L-ProGly(OEt) and L-Pro-L-Ala(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 I.R., UV-Vis, 1H NMR, 13C NMR, DEPT-135, 1H-13C COSY (HMQC) spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Selected compounds 5, 7, 9, 11, 16, 17 and 18 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.8–8.3 μM.
AB - A series of N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters 4–18 were prepared by coupling para-(ferrocenyl) ethynyl benzoic acid 3 to the amino acids GABA(OMe), GABA(OEt) and the dipeptide esters GlyGly(OMe), GlyGly(OEt), Gly-L-Ala(OMe), Gly-L-Ala(OEt), Gly-D-Ala(OMe), Gly-D-Ala(OEt), Gly-L-Leu(OEt), Gly-L-Phe(OEt), SarGly(OMe), SarGly(OEt), Sar-L-Ala(OEt), L-ProGly(OEt) and L-Pro-L-Ala(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 I.R., UV-Vis, 1H NMR, 13C NMR, DEPT-135, 1H-13C COSY (HMQC) spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Selected compounds 5, 7, 9, 11, 16, 17 and 18 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.8–8.3 μM.
KW - Bioorganometallic chemistry
KW - Cytotoxicity
KW - Dipeptides
KW - Ferrocene
KW - Lung cancer
UR - http://www.scopus.com/inward/record.url?scp=85025093350&partnerID=8YFLogxK
U2 - 10.1016/j.jorganchem.2017.07.019
DO - 10.1016/j.jorganchem.2017.07.019
M3 - Article
AN - SCOPUS:85025093350
SN - 0022-328X
VL - 846
SP - 379
EP - 388
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
ER -
