Synthesis and biological activity of ferrocenyl indeno[1,2-c]isoquinolines as topoisomerase II inhibitors

Wambang, Nathalie; Schifano-Faux, Nadège; Aillerie, Alexandre; Baldeyrou, Brigitte; Jacquet, Camille; Bal-Mahieu, Christine; Bousquet, Till; Pellegrini, Sylvain; Ndifon, Peter T.; Meignan, Samuel; Goossens, Jean‐François; Lansiaux, Amélie; Pélinski, Lydie

doi:10.1016/j.bmc.2015.12.033

Cited by 25 publications

(22 citation statements)

References 57 publications

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“…To circumvent drug resistance, a possible approach consists of designing and developing new therapeutic metal-based anticancer drugs [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. Several transition metals from the d-block of the periodic table (groups 3 to 12) and particularly essential trace metals [ 15 , 22 , 23 ], such as copper [ 24 , 25 , 26 , 27 , 28 , 29 ], are useful for the implementation of metal-based complexes in anticancer therapies.…”

Section: Introductionmentioning

confidence: 99%

Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II

Molinaro

Martoriati

Pélinski

et al. 2020

Cancers

131

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Organometallics, such as copper compounds, are cancer chemotherapeutics used alone or in combination with other drugs. One small group of copper complexes exerts an effective inhibitory action on topoisomerases, which participate in the regulation of DNA topology. Copper complexes inhibitors of topoisomerases 1 and 2 work by different molecular mechanisms, analyzed herein. They allow genesis of DNA breaks after the formation of a ternary complex, or act in a catalytic mode, often display DNA intercalative properties and ROS production, and sometimes display dual effects. These amplified actions have repercussions on the cell cycle checkpoints and death effectors. Copper complexes of topoisomerase inhibitors are analyzed in a broader synthetic view and in the context of cancer cell mutations. Finally, new emerging treatment aspects are depicted to encourage the expansion of this family of highly active anticancer drugs and to expend their use in clinical trials and future cancer therapy.

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Section: Introductionmentioning

confidence: 99%

Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II

Molinaro

Martoriati

Pélinski

et al. 2020

Cancers

131

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“…The most potent compound 149 (Table 6) with IC 50 of 0.95 mM displayed high DNA interaction, topoisomerase I and II inhibition, and an in vitro cytotoxicity comparable to etoposide as the reference drug. 131 de Jesús Cázares-Marinero et al, 132 synthesized seven new ferrocenyl compounds which showed strong antiproliferative activities against BC cell lines with IC 50 values ranging from 0.5 mM to 4.12 mM. Primary amides FcTAMPSA (compound 150) and 151 were the most cytotoxic compounds of all the three series (suberic, adipic and succinic) against MDA-MB-231 cells, with IC 50 values of 0.50 mM and 0.54 mM, respectively; while succinimide 152 was the most active compound against hormone dependent MCF-7 BC cells ( Table 6).…”

Section: The Ferrocenyl Functional Groupmentioning

confidence: 99%

Current research on anti-breast cancer synthetic compounds

et al. 2018

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“…Хочеться відмітити можливість проведення такої реакції за участю різноманітного набору поліфункціональних гідроксиловмісних аліфатичних амінів, у т.ч. аміноцукрів [80,81], а також за участю амінів, складовою частиною яких є металокомплекси [79]. Поштовхом до одержання такого великого масиву інденоізохінолінів стала вже згадана здатність деяких їхніх представників інгібувати білок PARP-1 (протизапальна дія), тоді як інші похідні є інгібіторами топоізомерази І та антагоністами RXR -ретиноїд Х рецепторів (протиракова активність).…”

Section: рис 25 імінотіазолідинонові похідні 234-триарилізохінолонівunclassified

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

Shablykina

Москвина

Савченко

et al. 2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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The review systematizes and analyzes the literature data (100 sources) regarding the recyclization of 3-arylisocoumarins (3-aryl-1H-isochromen-1-ones) under the action of primary N-nucleophiles that leads to the formation of 3-arylisoquinolones (3-arylisoquinolin-1(2H)-ones). This reaction may be carried out with a wide range of primary aminogroup-containing compounds: ammonia, primary aliphatic, aromatic, and heteroaromatic amines, hydrazine, and hydroxylamine. This transformation is not hindered by the presence of active functional groups (hydroxyl, acetal, carboxyl, ester, nitrile groups, or additional aminogroup) neither in 3-arylcoumarin nor in the primary amine. A special attention has been paid to reaction conditions (temperature regime, duration, solvent, catalysts), which may vary greatly. In particular, it is pointed out that in most cases to carry out high-temperature recyclization of 3-arylisocoumarins with ammonia and volatile amines with low molecular weight the use of closed reactors and high-pressure flasks was required. The cases of successful recyclization of 11,12-dihydrodibenzo[c,h]chromen-6-ones, indeno[1,2-c]isochromen-5(11H)-ones, isochromeno[4,3-c]chromen-6,11-dione and 5H-benzofuro[3,2-c]isochromen-5-one are reviewed separately. The polycondensated heterocyclic system of these compounds contains a 3-arylisocoumarin fragment. The biological activity data is presented for the compounds obtained via this transformation – 3-arylisoquinolin-1(2H)-ones, and also polycondensated systems that contain this fragment, e.g. 11,12-dihydrobenzo[c]phenanthridin-6(5H)-ones and 6H-indeno[1,2-c]isoquinoline-5,11-diones. The opportunities to use 3-arylisoquinolin-1(2H)-ones in the synthesis of other compounds of isoquinoline family, e.g. natural benzo[c]phenanthridinealocoloids, are demonstrated.

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Synthesis and biological activity of ferrocenyl indeno[1,2-c]isoquinolines as topoisomerase II inhibitors

Cited by 25 publications

References 57 publications

Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II

Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II

Current research on anti-breast cancer synthetic compounds

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

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