Synthesis, Characterization and in Vitro Biological Evaluation of Ru(Eta(6)-Arene)(N,N)Cl Pf6 Compounds Using the Natural Products Arenes Methylisoeugenol and Anethole
Five new organometallic Ru(II) compounds (VI-X) with the general formula Ru(eta(6)-arene)(N,N)CIPF6, where arene-N,N correspond to methylisoeugenol-bipyridine (VI); anethole-bipyridine (VII); methylisoeugenol-ethylenediamine (VIII); anethole-ethylenediamine (IX) and methylisoeugenol-1,2-diaminobenzene (X), have been synthesized, fully characterized and biologically evaluated in vitro. The reaction conditions based on the reduction of Ru(1,5-COD)Cl-2(n) in situ with methyleugenol and estragole, which are natural ligands, induced an alkene isomerization on the allylic substituent of coordinated arenes. The Ru(II)-arene bond formation and isomerization of the C=C bond on the allyl substituent was confirmed using 1H NMR spectroscopy; this result was validated for compound VIII by X-ray diffraction. An XRD analysis revealed the presence of both enantiomers of the complex in the single-crystal. Compounds IX and X exhibited a better cytotoxic activity in vitro than carboplatin, which is a commercial drug, against three human tumor cell lines (MCF-7, PC-3 and HT-29).
%0 Journal Article
%1 RN259
%A Delgado, R.A.
%A Galdamez, A.
%A Villena, J.
%A Reveco, P.G.
%A Thomet, F.A.
%D 2015
%I 2014 Elsevier B.V.
%J Journal of Organometallic Chemistry
%K 2 allyl bioorganometallic, bond cancer, complexes, cytotoxicity, diastereomers, dqcauchile drugs, isomerization, natural ovarian oxaliplatin, products, ru(ii) ruthenium, single-crystal, tumor-models,
%P 131-137
%R 10.1016/j.jorganchem.2014.09.005
%T Synthesis, Characterization and in Vitro Biological Evaluation of Ru(Eta(6)-Arene)(N,N)Cl Pf6 Compounds Using the Natural Products Arenes Methylisoeugenol and Anethole
%U /brokenurl#<Go to ISI>://WOS:000351637900020
%V 782
%X Five new organometallic Ru(II) compounds (VI-X) with the general formula Ru(eta(6)-arene)(N,N)CIPF6, where arene-N,N correspond to methylisoeugenol-bipyridine (VI); anethole-bipyridine (VII); methylisoeugenol-ethylenediamine (VIII); anethole-ethylenediamine (IX) and methylisoeugenol-1,2-diaminobenzene (X), have been synthesized, fully characterized and biologically evaluated in vitro. The reaction conditions based on the reduction of Ru(1,5-COD)Cl-2(n) in situ with methyleugenol and estragole, which are natural ligands, induced an alkene isomerization on the allylic substituent of coordinated arenes. The Ru(II)-arene bond formation and isomerization of the C=C bond on the allyl substituent was confirmed using 1H NMR spectroscopy; this result was validated for compound VIII by X-ray diffraction. An XRD analysis revealed the presence of both enantiomers of the complex in the single-crystal. Compounds IX and X exhibited a better cytotoxic activity in vitro than carboplatin, which is a commercial drug, against three human tumor cell lines (MCF-7, PC-3 and HT-29).
@article{RN259,
abstract = {Five new organometallic Ru(II) compounds (VI-X) with the general formula [Ru(eta(6)-arene)(N,N)CI]PF6, where arene-N,N correspond to methylisoeugenol-bipyridine (VI); anethole-bipyridine (VII); methylisoeugenol-ethylenediamine (VIII); anethole-ethylenediamine (IX) and methylisoeugenol-1,2-diaminobenzene (X), have been synthesized, fully characterized and biologically evaluated in vitro. The reaction conditions based on the reduction of [Ru(1,5-COD)Cl-2](n) in situ with methyleugenol and estragole, which are natural ligands, induced an alkene isomerization on the allylic substituent of coordinated arenes. The Ru(II)-arene bond formation and isomerization of the C=C bond on the allyl substituent was confirmed using 1H NMR spectroscopy; this result was validated for compound VIII by X-ray diffraction. An XRD analysis revealed the presence of both enantiomers of the complex in the single-crystal. Compounds IX and X exhibited a better cytotoxic activity in vitro than carboplatin, which is a commercial drug, against three human tumor cell lines (MCF-7, PC-3 and HT-29). },
added-at = {2019-12-04T03:57:35.000+0100},
author = {Delgado, R.A. and Galdamez, A. and Villena, J. and Reveco, P.G. and Thomet, F.A.},
biburl = {https://www.bibsonomy.org/bibtex/2a0512784dbc99c6b11903c1b9e43ae27/dqcauchile},
doi = {10.1016/j.jorganchem.2014.09.005},
interhash = {6e4083f47653b17b912e525681fc3ee8},
intrahash = {a0512784dbc99c6b11903c1b9e43ae27},
issn = {0022-328x},
journal = {Journal of Organometallic Chemistry},
keywords = {2 allyl bioorganometallic, bond cancer, complexes, cytotoxicity, diastereomers, dqcauchile drugs, isomerization, natural ovarian oxaliplatin, products, ru(ii) ruthenium, single-crystal, tumor-models,},
pages = {131-137},
publisher = {2014 Elsevier B.V.},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {Synthesis, Characterization and in Vitro Biological Evaluation of [Ru(Eta(6)-Arene)(N,N)Cl] Pf6 Compounds Using the Natural Products Arenes Methylisoeugenol and Anethole},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000351637900020},
volume = 782,
year = 2015
}