The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Andy G. Harry; James Murphy; William E. Butler; Rachel Tiedt; Áine Mooney; Jennifer C. Manton; Mary T. Pryce; Norma O'Donovan; Naomi Walsh; John Crown; Dilip K. Rai; Peter T.M. Kenny

doi:10.1016/j.jorganchem.2012.11.041

The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Andy G. Harry
, James Murphy
, William E. Butler
, Rachel Tiedt
, Áine Mooney
, Jennifer C. Manton
, Mary T. Pryce
, Norma O'Donovan
, Naomi Walsh
, John Crown
, Dilip K. Rai
, Peter T.M. Kenny

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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 ¹H NMR, ¹³C NMR, DEPT-135 and ¹H-¹³C 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 IC₅₀ values in the range of 3.2-7.2 μM.

Original language	English
Pages (from-to)	86-92
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	734
DOIs	https://doi.org/10.1016/j.jorganchem.2012.11.041
Publication status	Published - 15 Jun 2013
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Bioorganometallic chemistry
Cytotoxicity
Dipeptides
Ferrocene
Lung cancer

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10.1016/j.jorganchem.2012.11.041

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Harry, A. G., Murphy, J., Butler, W. E., Tiedt, R., Mooney, Á., Manton, J. C., Pryce, M. T., O'Donovan, N., Walsh, N., Crown, J., Rai, D. K., & Kenny, P. T. M. (2013). The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters. Journal of Organometallic Chemistry, 734, 86-92. https://doi.org/10.1016/j.jorganchem.2012.11.041

@article{eca21e10fb264c6b837544131e59ed1a,

title = "The synthesis, structural characterization and in vitro anti-cancer activity of novel N-\{6-(ferrocenyl) ethynyl-2-naphthoyl\} amino acid and dipeptide ethyl esters",

abstract = "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 1H NMR, 13C NMR, DEPT-135 and 1H-13C 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 IC50 values in the range of 3.2-7.2 μM.",

keywords = "Bioorganometallic chemistry, Cytotoxicity, Dipeptides, Ferrocene, Lung cancer",

author = "Harry, \{Andy G.\} and James Murphy and Butler, \{William E.\} and Rachel Tiedt and {\'A}ine Mooney and Manton, \{Jennifer C.\} and Pryce, \{Mary T.\} and Norma O'Donovan and Naomi Walsh and John Crown and Rai, \{Dilip K.\} and Kenny, \{Peter T.M.\}",

year = "2013",

month = jun,

day = "15",

doi = "10.1016/j.jorganchem.2012.11.041",

language = "English",

volume = "734",

pages = "86--92",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

}

Harry, AG, Murphy, J, Butler, WE, Tiedt, R, Mooney, Á, Manton, JC, Pryce, MT, O'Donovan, N, Walsh, N, Crown, J, Rai, DK & Kenny, PTM 2013, 'The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters', Journal of Organometallic Chemistry, vol. 734, pp. 86-92. https://doi.org/10.1016/j.jorganchem.2012.11.041

TY - JOUR

T1 - The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

AU - Harry, Andy G.

AU - Murphy, James

AU - Butler, William E.

AU - Tiedt, Rachel

AU - Mooney, Áine

AU - Manton, Jennifer C.

AU - Pryce, Mary T.

AU - O'Donovan, Norma

AU - Walsh, Naomi

AU - Crown, John

AU - Rai, Dilip K.

AU - Kenny, Peter T.M.

PY - 2013/6/15

Y1 - 2013/6/15

N2 - 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 1H NMR, 13C NMR, DEPT-135 and 1H-13C 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 IC50 values in the range of 3.2-7.2 μM.

AB - 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 1H NMR, 13C NMR, DEPT-135 and 1H-13C 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 IC50 values in the range of 3.2-7.2 μM.

KW - Bioorganometallic chemistry

KW - Cytotoxicity

KW - Dipeptides

KW - Ferrocene

KW - Lung cancer

UR - https://www.scopus.com/pages/publications/84876671848

U2 - 10.1016/j.jorganchem.2012.11.041

DO - 10.1016/j.jorganchem.2012.11.041

M3 - Article

AN - SCOPUS:84876671848

SN - 0022-328X

VL - 734

SP - 86

EP - 92

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Abstract

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Keywords

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