Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile

Synthesis and anti-cancer activity evaluation of new aurone derivatives

“…Various natural, semi-synthetic and synthetic derivatives of these structures have been investigated and reported with a wide range of biological applications 3,4 . Aurones, (Z)-2-benzylidenebenzofuran-3-(2H)-ones ( Figure 1c), constitute a less studied subclass of flavonoids although they are isosteres of flavones 5,6 . However, they have attracted attention with promising biological potential such as anti-microbial 7 , anti-cancer 8 , anti-leishmanial [9][10][11] , anti-histaminic 12 , antiinflammatory 13 , antioxidant 14 , insect anti-feedant 15 , herbicidal 16 , anti-HIV 17,18 , anti-HCV (hepatis C virus) 19,20 , anti-malarial 21,22 , ChE inhibitory 23,24 , MAO inhibitory 25 activities in the specified studies.…”

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

“…The geometry of the double bond has been established based on chemical shift (δ) value of the vinylic proton as well as carbon observed in the corresponding 1 H and 13 C NMR spectra. 14,35 Thus the present method does not require any use of organic solvent or acid or base or catalyst. In fact aurones were isolated in a practically pure form by simple Buchner filtration of the final aqueous reaction mixture, require neither work-up/extraction nor silica column purification.…”

“…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. 27 These methods suffers a severe limitation in the synthesis of hydroxy substituted aurones.…”

“…Due to our interest on aurones and isoaurones, 9,14,28 here we report a simple, green and environment friendly method for the synthesis of aurones from readily available benzofuranones and benzaldehydes.…”

A novel synthesis of aurones: Their <i>in vitro</i> anticancer activity against breast cancer cell lines and effect on cell cycle, apoptosis and mitochondrial membrane potential

“…The formation of Z-isomer is also supported by its thermodynamic stability compared to E-isomer. While the geometry of the double bond could be established on the basis of chemical shift () value of the vinylic proton as well as carbon observed in the corresponding 1 H and 13 C NMR spectra (Venkateswarlu et al, 2007;Hastings and Heller, 1972).…”