Search results for "Chalcone"

Phenylsulphonyl urenyl chalcone derivatives as dual inhibitors of cyclo-oxygenase-2 and 5-lipoxygenase

2005

Two series of phenylsulphonyl urenyl chalcone derivatives (UCH) with various patterns of substitution were tested for their effects on nitric oxide (NO) and prostaglandin E2 (PGE2) overproduction in RAW 264.7 macrophages. None of the tested compounds reduced NO production more than 50% at 10 microM but most of them inhibited the generation of PGE2 with IC50 values under the micromolar range. Me-UCH 1, Me-UCH 5, Me-UCH 9, Cl-UCH 1, and Cl-UCH 9 were selected to evaluate their influence on human leukocyte functions and eicosanoids generation. These derivatives selectively inhibited cyclo-oxygenase-2 (COX-2) activity in human monocytes being Me-UCH 5 the most potent (IC50 0.06 microM). Selecte…

Synthesis and anti-inflammatory activity of chalcone derivatives

1998

Chalcones and their derivatives were synthesized and evaluated for their anti-inflammatory activity. In vitro, chalcones 2, 4, 8, 10 and 13 inhibited degranulation and 5-lipoxygenase in human neutrophils, whereas 11 behaved as scavenger of superoxide. Only four compounds (4-7) inhibited cyclo-oxygenase-2 activity. The majority of these samples showed anti-inflammatory effects in the mouse air pouch model.

Cytotoxicity of two naturally occurring flavonoids (dorsmanin F and poinsettifolin B) towards multi-factorial drug-resistant cancer cells.

2015

Abstract Introduction The expression of diverse resistance mechanisms in cancer cells is one of the major barriers to successful cancer chemotherapy. Methods In the present study, we assessed the cytotoxicity of two naturally occurring flavonoids dorsmanin F ( 1 , a flavanone) and poinsettifolin B ( 2 , a chalcone) against 9 drug-sensitive and multidrug-resistant (MDR) cancer cell lines. The resazurin reduction assay was used to evaluate the cytotoxicity of these compounds, whilst caspase-Glo assay was used to detect caspase activation. Cell cycle, mitochondrial membrane potential (MMP) and levels of reactive oxygen species (ROS) were all analysed via flow cytometry. Results Compounds 1 and…

Cytotoxicity and modes of action of 4'-hydroxy-2',6'-dimethoxychalcone and other flavonoids toward drug-sensitive and multidrug-resistant cancer cell…

2014

Abstract Introduction Resistance of cancer to chemotherapy is a main cause in treatment failure. Naturally occurring chalcones possess a wide range of biological activities including anti-cancer effects. In this work, we evaluated the antiproliferative activity of three chalcones [4′-hydroxy-2′,6′-dimethoxychalcone ( 1 ), cardamomin ( 2 ), 2′,4′-dihydroxy-3′,6′-dimethoxychalcone ( 3 )], and four flavanones [( S )-(–)-pinostrobin ( 4 ), ( S )-(–)-onysilin ( 5 ) and alpinetin ( 6 )] toward nine cancer cell lines amongst which were multidrug resistant (MDR) types. Methods The resazurin reduction assay was used to detect the antiproliferative activity of the studied samples whilst flow cytometr…

Cytotoxicity of three naturally occurring flavonoid derived compounds (artocarpesin, cycloartocarpesin and isobavachalcone) towards multi-factorial d…

2015

Abstract Introduction Cancer remains an aggressive deadly disease, if drug resistance develops. This problem is aggravated by the fact that multiple rather than single mechanisms are involved in resistance and that multidrug resistance (MDR) phenomena cause inefficacy of many clinical established anticancer drugs. We are seeking for novel cytotoxic phytochemicals to combat drug-resistant tumour cells. Methods In the present study, we investigated the cytotoxicity of three naturally occurring flavonoids including two flavones artocarpesin (1) and cycloartocarpesin (2) and one chalcone, isobavachalcone (3) against 9 drug-sensitive and MDR cancer cell lines. The resazurin reduction assay was u…

Erratum to “Cissampeloflavone, a chalcone–flavone dimer from Cissampelos pareira”[Phytochemistry 64 (2003) 645–647]

2003

E-2-Benzylidenebenzocycloalkanones. IV. Studies on transmission of substituent effects on 13C NMR chemical shifts of E-2-(X-benzylidene)-1-tetralones…

2005

Abstract Single substituent parameter (SSP) and dual substituent parameter (DSP) analyses were applied to study the transmission of substituent effects on selected 13C NMR chemical shifts of the cyclic chalcone analogues, E-2-(4′-X-benzylidene)-1-tetralones (2) and E-2-(4′-X-benzylidene)-1-benzosuberones (3). In order to study how the geometry of the cyclic chalcone analogues affects the transmission of substituent effects similar investigations with the respective chalcones (4) were also performed. The results obtained earlier with the five-membered analogue E-2-(4′-X-benzylidene)-1-indanones (1) were also involved in the comparisons. Geometry optimization of the unsubstituted 1a, 2a, 3a a…

The reaction of aromatic α,β-unsaturated ketones with 4,5-diamino-1,6- dihydropyrimidin-6-ones

1994

The reaction of 4,5-diamino-1,6-dihydropyrimidin-6-ones 1 with one equivalent of the chalcones 2 leads in an acidic medium to the formation of the 2,4-diaryl-2,3,6,7-tetrahydro-1H-pyrimido[4,5-b][1,4]diazepin-6-ones 3a-m. The structure elucidation of the products is based on detailed nmr investigations including selective 13C[1H] decoupling experiments.

The effect of the fused-ring substituent on anthracene chalcones: crystal structural and DFT studies of 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-…

2018

Two new anthracene chalcones, namely 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one and 1-(anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one, have been successfully synthesized and the effect of the different fused ring substituent system attached to the anthracene chalcone derivative investigated. These compounds show a very narrow band gap due to the large p-conjugated systems, making them promising candidates as optoelectronic materials. Hirshfeld surface analysis has been carried out to show the contribution of inter­molecular contacts and weak inter­actions to supra­molecular stabilization.

Evaluation of the anti-inflammatory and analgesic activity of Me-UCH9, a dual cyclooxygenase-2/5-lipoxygenase inhibitor

2007

Abstract Recently, we reported the dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LO) activity by some phenylsulphonyl urenyl chalcone derivatives. 2,4-dichloro-4′ N [ N ′(4″methylphenylsulphonyl)urenyl] chalcone (Me-UCH9), was selected in the present study to determine its potential anti-inflammatory and analgesic effect after oral administration in several animal models related to the activation of COX-2 and 5-LO pathways. In the zymosan stimulated mouse air pouch model, Me-UCH9, reduced in a dose-dependent manner leukotriene B 4 (LTB 4 ) levels in pouch exudates obtained at 4 h, as well as prostaglandin E 2 (PGE 2 ) generated through COX-2 activation at 24 h. Tumor nec…