Synthesis of New Chiral (R)‐BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α‐Glucosidase Inhibitory Activity

Abstract

Series of new 3,3’‐disubstituted chiral (R)‐BINOL compounds have been synthesized with good yields and short reaction time under microwave‐irradiation. The titled compounds showed great antibacterial activity against gram‐positive and gram‐negative organisms. The results indicated that two compounds (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a) and (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) which bearing fluoro and nitro substitution on phenyl group has displayed highest inhibition against pathogens. All the derivatives evaluated in vitro against α‐glucosidase. The results indicates that all the target compounds have significant inhibitory activity and more potent than standard drug Acarbose (IC50 = 586.391 ± 14.017 μM). (R)‐3,3′‐bis(3,5‐dichlorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 b), (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a), (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) and (R)‐3,3′‐bis(3,5‐dimethylphenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 f) compounds shows strong inhibitors of α‐glucosidase, with the IC50 values of 25.341 ± 0.009 μM, 29.215 ± 0.017 μM, 30.294 ± 0.012 μM and 32.402 ± 0.041 μM, respectively.