Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

Compounds with dihydroquinoline-4(1H)-one nuclei have been reported in the literature for being important in the development of medicines due to their broad spectrum of activities. In this way, the structural knowledge of this class becomes relevant for obtaining new materials with desired biological properties. This study presents the structural elucidation of five halogenated dihydroquinolines, as well as the discussion about the effect on the molecular conformation of the type and position of halogen atom on aromatic rings. Compounds I and IV differ in halogen substitution on 2-phenyl ring, while compounds III and V differ in halogen substitution on the benzylidene ring. Moreover, compound II has a para-substituted 2-phenyl ring in their molecular structure. The crystal packing of all five molecules is mainly ruled by CeH/O and CeH$$$halogen interactions that form dimers and chains. The shift in position and the kind of the halogen in ring C shows a starring role in the conformation of the studied compounds, and the packaging of these compounds is more susceptible to variations when the halogen position changes.

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“…This kind of strategy allowed a complete assignment of the 1 H and 13 C nuclei (see S.I. ), and agrees with our previous report [22].…”

Section: Spectroscopy Characterizationsupporting

confidence: 91%

Structural comparison of five new halogenated dihydroquinoline-4(1H)-ones

Vaz

Michelini

Oliveira

et al. 2020

Journal of Molecular Structure

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“…Compounds 5 and 6 were obtained by reacting compound 4 with m-nitrobenzaldehyde and p-nitrobenzaldehyde under basic condition (Scheme 2). Their structure was verified by their 1 H NMR spectra (d'Oliverira et al 2018).…”

Section: Resultsmentioning

confidence: 99%

Different reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analogues

et al. 2019

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Non-enzyme catalyzed nucleophilic addition of reduced glutathione (GSH) onto two open-chain sulfonamide chalcones and two quinolinone-chalcone hybrids were studied to investigate the relationship between tumor cell cytotoxic activities and GSH-reactivities of the compounds. The consumption of the chalcones or the quinolinone-chalcone hybrids due to conjugation with GSH was evaluated by analytical high-performance liquid chromatography, and the formed diastereomeric adducts were identified by liquid chromatography-mass spectrometry. When the reaction was conducted with the open-chain chalcones, the equilibria were shifted towards formation of the respective GSH-conjugates. On the other hand, the cyclic chalcone derivatives with the quinolinone moiety were found to equilibrate to mixtures containing predominantly the reactants despite the strong electron withdrawing group present in the Bring of the compounds. The observed opposite behavior can be rationalized by reduced thiol-reactivity of the quinolinone-chalcone hybrids and fast decomposition of their GSH-conjugates. A combined X-ray diffraction and theoretical approach were used to explain the observed difference in the reactivities towards GSH. However, structural differences did not influence tumor cell (SF-295, PC-3 and HCT-116) cytotoxicity of the evaluated compounds. Accordingly, the altered GSH-reactivity seems to be not a determining factor in the tested tumor cell cytotoxic activity of the investigated compounds. Keywords Chalcones • Quinolinone • Glutathione • Michael reaction • Tumor cell cytotoxicity.

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“…Reports have been made where linking two distinct moieties together using various functional groups or spacers has resulted in synergizing the action of the resulting molecules [9][10][11][12][13][14][15][16][17]. In persuasion to the reports, we envisaged to fuse coumarin and chalcone nucleuses to form novel conjugates and evaluate the antioxidant potential of the conjugates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anti-oxidant activity of coumarinyl chalcones

Prasad

Loksh

2021

Futur J Pharm Sci

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Background The ability to inhibit oxidative stress has been established as the prime mechanism in treatment of several disease conditions. In view of this, two new series of coumarin–chalcone hybrid molecules (5a–o and 6a–o) were synthesized using various aromatic aldehydes. The structures of the compounds were confirmed using IR, 1HNMR and mass spectral analyses. The compounds were evaluated for their antioxidant potential against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydroxyl radicals in scavenging assays. Results Compounds 5o and 5k exhibited significant antioxidant potential as compared to the standard drug (ascorbic acid). Conclusions It can be concluded that the coumarin–chalcone treatment have the potential to be optimized further to generate scaffolds capable to treat many pathological conditions.

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Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

Cited by 15 publications

References 31 publications

Structural comparison of five new halogenated dihydroquinoline-4(1H)-ones

Structural comparison of five new halogenated dihydroquinoline-4(1H)-ones

Different reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analogues

Synthesis and anti-oxidant activity of coumarinyl chalcones

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