Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

Aurones as Modulators of ABCG2 and ABCB1: Synthesis and Structure–Activity Relationships

“…[31] With regards to the series 4 indanones, it was reported that the methine CH signals of E-benzylidene-2,3-dihydroindenones were found at 7.15-7.95 ppm and frequently overlapped with the aromatic proton signals. [33] This was duly observed in this study as well, in which the 1 H chemical shifts of the methine protons were found as singlets over a wide range (d = 6.21-7.89 ppm) or merged with the aromatic protons as multiplets.…”

Boronic-aurone Derivatives as Anti-Tubercular Agents: Design, Synthesis and Biological Evaluation

“…An important structural difference between CF1 and CF2 on one hand, and AL10 and AL11 on the other is the presence of 6-hydroxyl group on phenyl ring in the former. This suggests that although introducing more hydrophobic groups may be important, presence of hydroxyl groups appears to be a stronger contributing factor towards aurone activity [18,19]. Compared to NIH with MIC of 0.013 mg/mL, CF1 and CF2 with MICs of 0.083 mg/mL and 0.100 mg/ mL respectively exhibit fairly significant anti-tubercular activity.…”

“…Aurones have been shown to have a wide range of biological activity, including anti-inflammatory and antimicrobial activity [17,18]. The biological activities of aurones have been demonstrated to be affected by the number of hydroxyl groups present on the rings [19]. Previous studies have also shown that the active site of Ag85 shows fairly good tolerance for a number of substrates capable of fitting into the trehalose monomycolate-binding pocket [4,[9][10][11][12][13].…”

"On water" synthesis of aurones: first synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia

“…It was interesting to observe that the exclusive formation of β-hydroxy product (3) without detectable amount of aurone (4a) at rt. At higher temperatures, the reaction gave a mixture of β-hydroxy product (3) and aurone (4a), which were separated by column chromatography (entry [3][4][5]. Surprisingly at reflux temperature, the reaction proceeded cleanly and exclusively gave aurone (4a) in good yield.…”

“…Aurones possess a wide spectrum of pharmacological activities 2 such as anti-tumor/anti-cancer, [3][4][5][6] anti-diabetic, 7 anti-inflammatory, 8 anti-oxidant, 9 anti-bacterial, 10 anti-Alzheimer's, 11 insect antifeedant, 12 and tyrosinase. 13 Various approaches have been reported for the synthesis of aurones: (i) oxidative cyclization of 2'-hydroxychalcones using Hg(OAc)2 14,15 or Thallium(III) nitrate; 16 (ii) cyclization of 2'-acetoxychalcones using tetrabutylammonium tribromide; 17 (iii) ring closing reaction of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols catalyzed by AuCl2; 18 (iv) recently via dihaloacrylic acids 19 and Cu-catalyzed cyclization of (2-halogenphenyl)(3-phenyloxiran-2-yl)methanones; 20 (v) the more convenient and practical use involves the condensation of benzofuran-3(2H)-ones with aryl aldehydes using various acidic or basic catalysts 21 under different conditions, such as KOH or NaOH/CH3OH, 10 HCl/CH3COOH, 22 Al2O3/CH2Cl2, 23 KF-Al2O3/CH2Cl2/MW, 24 EDDA/CH3CN/Ultrasound, 25 acetic anhydride 26 and using deep eutectic solvent.…”