34000-26-5Relevant academic research and scientific papers
Differences in antioxidant potential of chalcones in human serum: In vitro study
Ivkovi?, Branka,Jankovi?, Tamara,Kotur-Stevuljevi?, Jelena,Turkovi?, Nemanja,Vuji?, Zorica
, (2020/04/17)
Introduction: An imbalance between oxidants and antioxidants in favour of oxidants, potentially leading to damage, is termed oxidative stress. Antioxidants (AO), either enzymatic or non-enzymatic, are the ones that can reduce diverse effects of pro-oxidan
Novel chalcone derivatives containing a 1,2,4-triazine moiety: Design, synthesis, antibacterial and antiviral activities
Tang, Xu,Su, Shijun,Chen, Mei,He, Jun,Xia, Rongjiao,Guo, Tao,Chen, Ying,Zhang, Cheng,Wang, Jun,Xue, Wei
, p. 6011 - 6020 (2019/03/12)
A series of novel chalcone derivatives containing the 1,2,4-triazine moiety were synthesized and their structures were confirmed by 1H NMR, 13C NMR and elemental analyses. Antiviral bioassays revealed that most of the compounds exhibited good antiviral activity against tobacco mosaic virus (TMV) at a concentration of 500 μg mL-1. The designated compound 4l was 50% effective in terms of curative and protective activities against TMV with 50% effective concentrations (EC50) of 10.9 and 79.4 μg mL-1, which were better than those of ningnanmycin (81.4 and 82.2 μg mL-1). Microscale thermophoresis (MST) also showed that the binding of compound 4l to coat protein (TMV-CP) yielded a Kd value of 0.275 ± 0.160 μmol L-1, which was better than that of ningnanmycin (0.523 ± 0.250 μmol L-1). At the same time, molecular docking studies for 4l with TMV-CP (PDB code:1EI7) showed that the compound was embedded well in the pocket between the two subunits of TMV-CP. Meanwhile, compound 4a demonstrated excellent antibacterial activities against Ralstonia solanacearum (R. solanacearum), with an EC50 value of 0.1 μg mL-1, which was better than that of thiodiazole-copper (36.1 μg mL-1) and bismerthiazol (49.5 μg mL-1). The compounds act by causing folding and deformation of the bacterial cell membrane as observed using scanning electron microscopy (SEM). The chalcone derivatives thus synthesized could become potential alternative templates for novel antiviral and antibacterial agents.
From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation
Kumar, Singam Naveen,Bavikar, Suhas Ravindra,Pavan Kumar, Chebolu Naga Sesha Sai,Yu, Isaac Furay,Chein, Rong-Jie
, p. 5362 - 5366 (2018/09/12)
A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.
Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin
Dias, Tatiana A.,Duarte, Cecília L.,Lima, Cristovao F.,Proen?a, M. Fernanda,Pereira-Wilson, Cristina
, p. 500 - 510 (2013/10/01)
A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the respective chalcone precursors. The antiproliferative activity of halogenated derivatives increases as the substituent in the 3- or 4-positon of the B-ring goes from F to Cl and to Br. In addition, halogens in position 3 enhance anticancer activity in chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully prepared and presented high anticancer activity as shown by their cell growth and cell cycle inhibitory potential against HCT116 cells, superior to that of quercetin, used as a positive control.
Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols
Zhao, Dongbing,Beiring, Bernhard,Glorius, Frank
supporting information, p. 8454 - 8458 (2013/09/02)
Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright
Understanding the cardioprotective effects of flavonols: Discovery of relaxant flavonols without antioxidant activity
Cheng, Xue Qin,Chen, Xingqiang,Hughes, Richard A.,Williams, Spencer J.,Woodman, Owen L.
, p. 1874 - 1884 (2008/12/21)
3′,4′-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can reduce injury after myocardial ischemia and reperfusion and thus is a promising small molecule for the treatment of cardiovascular disease. Like all vasoactive flavonols reported to date, DiOHF is both relaxant and antioxidant, hindering investigation of the relative contribution of each activity for the prevention of reperfusion injury. This study investigates structure-activity relationships of variations at the 3′ and 4′ positions of the B ring of DiOHF and vasorelaxant and antioxidant activities. Relaxation of rat isolated aortic rings precontracted with KCl revealed that the most active flavonols were those with a 4′-hydroxyl group, with the opening of potassium channels as a possible contributing mechanism. For the antioxidant activity, with the exception of DiOHF, none of the flavonols investigated were able to significantly scavenge superoxide radical, and none of the three most potent vasorelaxant flavonols could prevent oxidant-induced endothelial dysfunction. The discovery of single-acting vasorelaxant flavonols without antioxidant activity, in particular 4′-hydroxy-3′-methoxyflavonol, will assist in investigating the mechanism of flavonol-induced cardioprotection.
Inhibition of amine oxidases activity by 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives
Manna, Fedele,Chimenti, Franco,Bolasco, Adriana,Secci, Daniela,Bizzarri, Bruna,Befani, Olivia,Turini, Paola,Mondov, Bruno,Alcaro, Stefano,Tafi, Andrea
, p. 3629 - 3633 (2007/10/03)
A novel series of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives have been synthesised and investigated for the ability to inhibit selectively monoamine oxidases, swine kidney oxidase, and bovine serum amine oxidase. The newly synthesised compounds 1-6 proved to be reversible and non-competitive inhibitors of all types of the assayed amine oxidases. Compounds inhibit monoamine oxidases potently, displaying low I50 values of particular interest. In particular 1-acetyl-3-(2,4-dihydroxyphenyl)-5-(3-methylphenyl)-4,5-dihydro-(1H)-pyrazole 6 showed to be a potent monoamine oxidase inhibitor with a Ki of about 10-8 M. Further insights in the theoretical evaluation of the possible interactions between the compounds and monoamine oxidase B have been developed through a computational approach.
A concerted synthesis of hydroxychalcones, flavanones and benzo[b]furans through palladium-catalysed reactions
De, Mahuya,Majumdar, Dyuti P.,Kundu, Nitya G.
, p. 665 - 674 (2007/10/03)
A convenient palladium-catalysed procedure for the synthesis of o-hydroxychalcones, flavanones and benzo[b]furans is described where o-iodophenyl acetate was used as a common precursor.
Thermal Isomerization Equilibrium between 2'-Hydroxychalcones and Flavanones
Hoshino, Yukio,Takeno, Noboru
, p. 2903 - 2904 (2007/10/02)
Nine substituted 2'-hydroxychalcones and the corresponding flavanones were heated separately at 230 +/- 0.2 deg C in nitrogen atmosphere.Both materials were mutually isomerized under these reaction conditions and the equilibrium constants of this isomerization were measured by means of HPLC analyses.The substituent effect on the equilibrium is discussed and thermodynamic functions (ΔG, ΔH, and ΔS) are calculated.
The Direct Preparation of Flavones from 2'-Hydroxychalcones Using Disulfides
Hoshino, Yukio,Oohinata, Toshinori,Takeno, Noboru
, p. 2351 - 2352 (2007/10/02)
Flavone was obtained by a reaction of 2'-hydroxychalcone with disulfides in good yield.Among several disulfides, diphenyl disulfide gave the best result.Under the same conditions, some flavones were obtained from the corresponding 2'-hydroxychalcones in satisfactory yields.
