Nitrogen-Containing Heterocyclic Quinones: A Class of Potential Selective Antitumor Agents

Garuti, L.; Roberti, Marinella; Pizzirani, Daniela

doi:10.2174/138955707780619626

Cited by 78 publications

(52 citation statements)

References 59 publications

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“…Heterocyclic compounds with naphthoquinone fragment are well known as anticancer drugs, such as doxorubicin, daunorubicin, mitoxantrone and mitomycine C. 37,38) Thus, the reaction of 3a-d with 1,4-naphthoquinone 8 in refluxing acetic acid afforded compounds 9a-d (Chart 3). The structure of the isolated adducts was confirmed by elemental analysis and spectral data.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-<i>d</i>]thiazoles Incorporating Pyrazole Moiety

2015

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The knöevenagel condensation of 3-phenyl-4-thioxo-2-thiazolidinone (1) with 1-phenyl-3-aryl-1H-pyrazole-4-carbaldehydes 2a-d in refluxing glacial acetic acid or in polyethylene glycol-400 (PEG-400) at room temperature without catalyst, afforded the corresponding 5-hetarylmethylene derivatives 3a-d.[4+2] Cycloaddition reaction of compounds 3 with N-arylmaleimides, acrylonitrile and ethyl acrylate afforded thiopyrano[2,3-d]thiazole derivatives 5a-p. The anticancer activity of some of the newly synthesized compounds was investigated against different human cancer cell lines (MCF7 and HEPG2) and confirmed by molecular docking. Moreover, the structure for one representative example of the new products was confirmed by X-ray crystallography. The structure of all the newly synthesized compounds was established by elemental and spectral data.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-<i>d</i>]thiazoles Incorporating Pyrazole Moiety

2015

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“…8 In our laboratory, the study for development of various heterocyclic quinones as an anticancer agent with topo II inhibitory activity has been continued. [9][10][11] However, the intrinsic cytotoxicity related to these benzonaphthofurandiones 12,13 prompted us to pursue the preparation and cytotoxicity study on the more promising anlogues towards the five human tumor cell lines.…”

Section: 6mentioning

confidence: 99%

Synthesis, Cytotoxicity and Topoisomerase II Inhibitory Activity of Benzonaphthofurandiones

Rhee

Kwon²,

Chung

et al. 2011

Bulletin of the Korean Chemical Society

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Benzonaphthofurandiones containing four coplanar fused aromatic rings were synthesized and evaluated for their cytotoxicity against five human cancer cell lines, and their inhibitory activity on topoisomerases. These benzonaphthofurandiones were prepared by condensation of 2,3-dichloronaphthoquinone and three aromatic diols with base catalysts in alcohol. The synthesized compounds were o-alkylated with six dialkylaminoalkyl halides. The hydroxy derivatives (8a-8g) exhibited relatively potent cytotoxicity among the prepared compounds. These compounds were evaluated as excellent inhibitors against topoisomerase II (topo II). Especially, the hydroxy analogue with branched methyl side chain (8e) showed high cytotoxicity against cancer cell lines and good inhibitory activity on topo II.

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“…5 The reduction of quinones and the oxidation of hydroquinones have been related to cytotoxicity and anti-cancer activity. [6][7][8] Besides, it is known that quinone derivatives display a variety of biological activities, including fungicidal, through the formation of semi-quinone radicals. 9 In the past, significant work of our group has been devoted to the synthesis, mechanism of formation and biological evaluation of quinones and hydroquinones.…”

Section: Introductionmentioning

confidence: 99%

Location, Orientation and Dynamics of Two Molecules With Mitochondrial Activity Dissolved in Anionic Lyomesophase: A ²h-NMR and Md Study

Bahamonde-Padilla¹,

Martínez-Cifuentes²,

Muñoz-Masson³

et al. 2012

J. Chil. Chem. Soc.

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ABSTRACT4,4-Dimethyl-5,8-dihydroanthracene-1,9,10(4H)-trione (Q1) and 9,10-Dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone (Q2), two molecules that inhibit cancer cell respiration, were selectively deuterated and dissolved in an anionic discotic nematic lyotropic liquid crystal (dnllc) solution. The solution provides a magnetic field oriented anisotropic medium, where the location, average orientation and dynamics of Q1 and Q2 were examined by measuring 2 H-NMR quadrupole splittings (Dn Q ) and 2 H longitudinal relaxation times (T 1 ). The NMR data shows that both molecules are strongly attached to the aggregate and, when dissolved, increase the alignment of the interface components with the magnetic field. However they present different average orientations. To assist with the interpretation of the experimental results, 300ns Molecular Dynamics (MD) trajectories of a bilayer model of the aggregate were calculated. The results show that both molecules spontaneously diffuse inside the bilayer, to locate in the limit between the hydrophobic core and the interface. The orientations of both molecules in the aggregate are determined by the formation of H-bonds with water.

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Nitrogen-Containing Heterocyclic Quinones: A Class of Potential Selective Antitumor Agents

Cited by 78 publications

References 59 publications

Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-<i>d</i>]thiazoles Incorporating Pyrazole Moiety

Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-<i>d</i>]thiazoles Incorporating Pyrazole Moiety

Synthesis, Cytotoxicity and Topoisomerase II Inhibitory Activity of Benzonaphthofurandiones

Location, Orientation and Dynamics of Two Molecules With Mitochondrial Activity Dissolved in Anionic Lyomesophase: A ²h-NMR and Md Study

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