Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives

Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek

doi:10.1016/j.ejmech.2015.06.052

Cited by 166 publications

(85 citation statements)

References 151 publications

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“…They have received considerable attention due to their wide range of biological actions and have been used as a scaffold in the development of anticancer, antioxidant, antiangiogenic, and anti-inflammatory agents [5]. A number of natural and synthetic chalcones have been shown to possess anti-parasitic activities including licochalcone A 1, a natural prenylated chalcone isolated from liquorice root (Glycyrrhiza glabra), and a potent anti-leishmanial agent [6]. However, the therapeutic use of chalcones has been limited due to their poor bioavailability and rapid metabolic clearance from biological systems [7].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antitrypanosomal activities of novel pyridylchalcones

Bhambra

Ruparelia

Tan

et al. 2017

European Journal of Medicinal Chemistry

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a b s t r a c tA library of novel pyridylchalcones were synthesised and screened against Trypanosoma brucei rhodesiense. Eight were shown to have good activity with the most potent 8 having an IC 50 value of 0.29 mM.Cytotoxicity testing with human KB cells showed a good selectivity profile for this compound with a selectivity index of 47. Little activity was seen when the library was tested against Leishmania donovani. In conclusion, pyridylchalcones are promising leads in the development of novel compounds for the treatment of human African trypanosomiasis (HAT).

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Section: Introductionmentioning

confidence: 99%

“…Pyridylchalcones, such as 3 and 4, have been found to exhibit both antimalarial and anti-leishmanial activity [6,11,12,13]. However, there are no examples of them being tested against Trypanosoma brucei.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitrypanosomal activities of novel pyridylchalcones

Bhambra

Ruparelia

Tan

et al. 2017

European Journal of Medicinal Chemistry

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“…Chalcones, or 1,3-diaryl-2-propen-1-ones, are a class of polyphenolic compounds belonging to the flavonoid family which possess a wide range of pharmacological activities, including anti-cancer [1], anti-infective [2], anti-diabetic [3], and anti-oxidant [4] activities. These one compounds are obtained by means of the Claisen-Schmidt condensation reaction between aldehydes and ketones using basic or acidic catalysis [5].…”

Section: Introductionmentioning

confidence: 99%

N-{4-[(2E)-3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl]phenyl}quinoline-3-carboxamide

Polo-Cuadrado

Trilleras

Cabrera

2017

Molbank

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An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenyl) quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl 2 ), following the addition of 4-aminoacetophenone. Then, a typical Claisen-Schmidtreactionwas made between 2 and piperonal using KOH solution as a catalystin ethanol, under ultrasonic irradiation. The structure of the target compound was established by FTIR (Fourier-transform infrared spectroscopy), HRMS, 1 H and 13 C-NMR.

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“…Chalcones are widely explored as potential lead compounds for new therapeutic agents, and antitumor properties of the compounds are among the most often studied (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17).…”

mentioning

confidence: 99%

“…The residue was purified on silica gel chromatographic column in methylene chloride to give a colorless solid, yield 154 mg (43%). (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), the formed solid was filtered off, washed with water and ethanol, and crystallized. Cytotoxicity assays in vitro on A549, HCT116 and HeLa cell lines Multiwell (24-well) plates were seeded at 3 9 10 3 cells/ well in RPMI1640 medium supplemented with 10% FBS and antibiotics (penicillin/streptomycin), and cells were allowed to attach overnight.…”

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confidence: 99%

Influence of S‐Oxidation on Cytotoxic Activity of Oxathiole‐Fused Chalcones

et al. 2016

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Synthesis, in vitro cytotoxic activity, and interaction with tubulin of oxidized, isomeric 1-(5-alkoxybenzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-ones and 1-(6-alkoxybenzo[d][1,3]oxathiol-5-yl)-3-phenylprop-2-en-1-ones are described. Most of the compounds demonstrated cytotoxic activity at submicromolar concentrations. It was found that oxidation of sulfur atom of the oxathiole-fused chalcones strongly influenced activity of the parent compounds, and that depending on relative position of the sulfur atom in the molecule, the activity was either increased or diminished. For isomers with sulfur atom para to the chalcone carbonyl group, oxidation led to increase in activity, while for isomers with sulfur atom meta to the carbonyl the activity dropped down. It was demonstrated that the compounds interact with tubulin at the colchicine binding site, and the interaction was evaluated using molecular modeling. It was concluded that the observed profound influence of oxidation of the sulfur atom on cytotoxic activity cannot be solely related to interaction of the compounds with tubulin.

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Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives

Cited by 166 publications

References 151 publications

Synthesis and antitrypanosomal activities of novel pyridylchalcones

Synthesis and antitrypanosomal activities of novel pyridylchalcones

N-{4-[(2E)-3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl]phenyl}quinoline-3-carboxamide

Influence of S‐Oxidation on Cytotoxic Activity of Oxathiole‐Fused Chalcones

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