Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction

Plażuk, Damian; Rychlik, Błażej; Błauż, Andrzej; Domagała, Sławomir

doi:10.1016/j.jorganchem.2012.05.042

Cited by 29 publications

(16 citation statements)

References 50 publications

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“…C 13 H 10 ORu requires C, 55.1; H, 3.6%; IR (KBr) ν max /cm −1 : 3212s, 3092w, 2090s, 1625vs, 1449s, 1411w, 1394w, 1375m, 1350w, 1339w, 1324s, 1101m, 1072s, 1034m, 1023w, 1001m, 992m, 882m, 869w, 849w, 841w, 823m, 765m, 725m, These compounds were prepared by applying the previously described procedure for the synthesis of 1-aryl-4-ferrocenyl-1,2,3-triazoles. 13 7-Deacetamido-7-(4-ferrocenyl-1H-1,2,3-triazol-1-yl)-colchicine 7-Deacetamido-7-(4-ferrocenoyl-1H-1,2,3-triazol-1-yl)-colchicine Fc2. This compound was prepared in 77% yield (118 mg) according to general procedure B starting from 95 mg (0.248 mmol) of 5 and 59 mg (0.248 mmol) of 15.…”

Section: General Procedures Asynthesis Of ϖ-Alkynoylruthenocenes 19-23mentioning

confidence: 99%

“…7-azido-7-deacetamidocolchicine 5 with ethynylmetallocenes 12-13, ϖ-alkynoylferrocenes 15-18 or ϖ-alkynoylruthenocenes 20-23 by following a previously described method. 13 Compound 5 was prepared according to a known procedure starting from colchicine (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…HSQC or HMQC, 1 H-13 C HMBC) NMR spectra were recorded on a Bruker ARX 600 MHz (spectrometer frequency 600.3 MHz for 1 H and 150.9 MHz for 13 C). Chemical shifts for the NMR spectra are referenced relative to the residual protons in the deuterated solvent (CDCl 3 δ = 7.26 ppm for 1 H and δ = 77.00 ppm for 13 C{ 1 H}).…”

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confidence: 99%

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Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines

et al. 2017

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A series of ferrocenyl and ruthenocenyl conjugates with colchicine bearing a 1,2,3-triazole moiety were synthesized and their anticancer properties were evaluated. We found that the most potent metallocenyl derivatives Rc4 and Rc5 are 6-7 times more cytotoxic toward HepG2 cells, while Fc4 and Fc5 are two times more cytotoxic toward HCT116 cells as colchicine. We also found that compounds Fc4, Fc5, Rc1 and Rc3-Rc5 are able to induce apoptosis, while compound Fc2 arrests mitosis.

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Section: General Procedures Asynthesis Of ϖ-Alkynoylruthenocenes 19-23mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines

et al. 2017

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“…The required ω‐metallocenylalkynes 8 – 14 were prepared in Friedel–Crafts acylation of ferrocene or ruthenocene with acyl trifluoroacetates generated in situ in the presence of trifluoromethanesulfonic acid according to a reported procedure [29b, 37] . Next, azide 5 reacts with acetylenes 7 – 14 at RT for 3 days in a mixture of tert ‐butanol and water in the presence of Cu I complex with TTTA as a catalyst (freshly prepared form copper(II) sulfate, sodium ascorbate and TTTA [38] ) to give 1,2,3‐triazoles T1 – 8 in 19–79 % yields, isolated by column chromatography on silica. The structures of the obtained compounds were confirmed by 1D and 2D NMR, IR and MS spectroscopy, and elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Ferrocenyl and Ruthenocenyl Analogues of Etoposide: Discovery of a Novel Dual Inhibitor of Topoisomerase II Activity and Tubulin Polymerization

Chrabąszcz

Błauż

Gruchała

et al. 2021

Chemistry A European J

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Two series of the ferrocenyl and ruthenocenyl analogues of etoposide bearing 1,2,3‐triazolyl or aminoalkyl linker were synthesized and evaluated for their cytotoxic properties, influence on the cell cycle, ability to induce tubulin polymerization, and inhibition of topoisomerase II activity. We found that the replacement of the etoposide carbohydrate moiety with a metallocenyl group led to organometallic conjugates exhibiting differentiated antiproliferative activity. Biological studies demonstrated that two ferrocenylalkylamino conjugates were notably more active than etoposide, with submicromolar or low‐micromolar IC50 values towards SW620, etoposide‐resistant SW620E, and methotrexate‐resistant SW620M cancer cell lines. Moreover, the simplest ferrocenylmethylamino conjugate exerted dual inhibitory action against tubulin polymerization and topoisomerase II activity while other studied compounds affected only topoisomerase II activity.

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“…The introduction of a 3,5-dihydroxyphenyl in compound 64 led to a significant decrease in the anticancer activity. Compound 62 exhibited cytotoxic activity against the hormone-dependent MCF-7 cancer cell lines at high concentrations of IC 50 = 48.9 [68].…”

Section: Ferrocene-based Compounds With Anticancer Activitymentioning

confidence: 99%

Ferrocene-Based Compounds with Antimalaria/Anticancer Activity

2019

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Malaria and cancer are chronic diseases. The challenge with drugs available for the treatment of these diseases is drug toxicity and resistance. Ferrocene is a potent organometallic which have been hybridized with other compounds resulting in compounds with enhanced biological activity such as antimalarial and anticancer. Drugs such as ferroquine were developed from ferrocene and chloroquine. It was tested in the 1990s as an antimalarial and is still an effective antimalarial. Many researchers have reported ferrocene compounds as potent compounds useful as anticancer and antimalarial agents when hybridized with other pharmaceutical scaffolds. This review will be focused on compounds with ferrocene moieties that exhibit either an anticancer or antimalarial activity.

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Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction

Cited by 29 publications

References 50 publications

Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines

Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines

Synthesis and Biological Activity of Ferrocenyl and Ruthenocenyl Analogues of Etoposide: Discovery of a Novel Dual Inhibitor of Topoisomerase II Activity and Tubulin Polymerization

Ferrocene-Based Compounds with Antimalaria/Anticancer Activity

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