1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 z Organic & Supramolecular Chemistry Synthesis of New Chiral (R)-BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α-Glucosidase Inhibitory Activity Ashok Reddy Ankireddy, [a] Kalyani Paidikondala, [a] Rambabu Gundla,* [a] Tuniki Balaraju, [a] Ramakanth Pagadala, [b] and Venkanna Banothu [c] 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’-binaphtha- lene]-2,2’-diol (6a) and (R)-3,3’-bis(4-nitrophenyl)-[1,1’-binaph- thalene]-2,2’-diol (6d) which bearing fluoro and nitro substitu- tion 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 (IC 50 = 586.391 � 14.017 μM). (R)-3,3’- bis(3,5-dichlorophenyl)-[1,1’-binaphthalene]-2,2’-diol (6b), (R)- 3,3’-bis(3,5-difluorophenyl)-[1,1’-binaphthalene]-2,2’-diol (6a), (R)-3,3’-bis(4-nitrophenyl)-[1,1’-binaphthalene]-2,2’-diol (6d) and (R)-3,3’-bis(3,5-dimethylphenyl)-[1,1’-binaphthalene]-2,2’- diol (6f) compounds shows strong inhibitors of α-glucosidase, with the IC 50 values of 25.341 � 0.009 μM, 29.215 � 0.017 μM, 30.294 � 0.012 μM and 32.402 � 0.041 μM, respectively. Introduction Present day global healthcare system is levied a heavy burden by the bacterial infections derived from hospital itself. The antibiotics are commonly used for bacterial infections. However bacteria have strengthened themselves against all present day therapeutic options because of the prolonged, dispropor- tionate and excessive usage. Thus the growing capacity of bacterial resistance to the present day antibiotics surfaces a chronic medical challenge especially in treating pathogenic infections. [1–3] Therefore the present day commercial antibiotics need to be replaced with compounds which are more potent and less sensitive. Bacterial resistance against various anti- biotics is spreading its tentacles across the globe causing serious threats to human health. Presently Gram-positive or Gram-negative bacterial strains are massively tormenting huge number of people. Hence, novel drug invention is the prime need of the hour to prevent common infections leading to serious illnesses. [4–8] Antibiotics stake prime position to provide solution to the microbial infection. However presently for the growth of the bacterial intensity, fresh antibiotic agents need to be invented. Therefore the organic and medicinal chemists must come up with more potent antibacterial drugs to replace the existing medication and combat the bacterial resistance in general. For a decade intense research has been going on various organic compounds to answer this issue. The BINOL ring framework is among these bioactive scaffolds that have been considered one of the mainstays in providing novel chemical scaffolds for many drugs. Chiral bicyclic macrocycles, [9] Imidazole based dicationic macrocycles, [10] chiral dendrimers, [11,12] Imidazolium salts at 3,3’ substitution on BINOL [13] and [2,1-b:1’,2’-d][1,6] dioxacycloalkenes [14] having BINOL as core unit show antibacte- rial activity. Very few reports are available on 3,3’-disubstituted chiral (R)-BINOL. Diabetes mellitus generally coined as diabetes (Type I and Type II) is the worst metabolic disorders spread across the world. Diabetes is a group metabolic disorder characterized with high blood sugar levels over a long time. Frequent urination, increased thirst, and increased hunger are caused by high blood sugar, which if not addressed to, will result in serious health issues such as diabetic ketoacidosis, hyper- osmolar hyperglycemic state, or death, cardiac and vascular diseases, thrombosis, stroke, chronic kidney disease, foot ulcers, and damage to the eyes. [15,16,17] Causes of diabetes are either the pancreas fail to produce enough insulin, or the cells of the body fail to respond adequately to the insulin produced. In the brush border of the intestine α-glucosidase is present. It catalyzes the hydrolysis of polysaccharides to monosaccharides that leads to post-parandial hyperglycemia. [18–20] High glucose levels in the blood (hyperglycemia) adversely affect different [a] A. R. Ankireddy, Dr. K. Paidikondala, Dr. R. Gundla, Dr. T. Balaraju Department of Chemistry, Gitam University, Hyderabad, Rudraram Mandal, Sangareddy District, Patancheru, Hyderabad, Telangana 502329, India E-mail: rambabu.gundla@gitam.edu [b] Dr. R. Pagadala Department of Chemistry, CVR College of Engineering (Autonomous), Hyderabad, Telangana 501510, India [c] Dr. V. Banothu Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, Kukatpally Housing Board Colony, Hyderabad, Telangana 500085, India Supporting information for this article is available on the WWW under https://doi.org/10.1002/slct.201803937 Full Papers DOI: 10.1002/slct.201803937 5563 ChemistrySelect 2019, 4, 5563–5569 © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim