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Amylase and -Glucosidase molecules Article Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase Mezna Saleh Altowyan 1, Assem Barakat 2,3,* , Abdullah Mohammed Al-Majid 2 and H.A. Al-Ghulikah 1 1 Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh 1167, Saudi Arabia; [email protected] (M.S.A.); [email protected] (H.A.A.-G.) 2 Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; [email protected] 3 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt * Correspondence: [email protected]; Tel.: +966-11467-5901; Fax: +966-11467-5992 Received: 3 June 2019; Accepted: 21 June 2019; Published: 25 June 2019 Abstract: Inhibition of α-amylase and α-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/ benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[b]furan scaffold (compounds 2a–f), with a substituted isatin (compounds 3a–c) and heterocyclic amino acids (compounds 4a,b). The target spiroindolone analogues 5a–r were evaluated for their potential inhibitory activities against the enzymes α-amylase and α-glucosidase. Preliminary results indicated that some of the target compounds exhibit promising α-amylase and α-glucosidase inhibitory activity. Among the tested spiroindolone analogues, the cycloadduct 5r was found to be the most active (IC50 = 22.61 0.54 µM and 14.05 1.03 µM) as α-amylase and α-glucosidase inhibitors, with selectivity ± ± indexes of 0.62 and 1.60, respectively. Docking studies were carried out to confirm the binding interaction between the enzyme active site and the spiroindolone analogues. Keywords: spiroindolone; antidiabetic; hypoglycemic; α-amylase; α-glucosidase 1. Introduction Diabetes is a serious disease, classified as chronic, that occurs either when the pancreas does not produce enough insulin (a hormone that regulates blood glucose), or when the body cannot effectively use the insulin well [1]. According to the World Health Organization more than 400 million people live with diabetes and this number may raise to 592 million by 2035, due to increased incidence of adult onset diabetes (T2DM) [2,3]. Increased blood glucose levels, a common effect of uncontrolled diabetes, may, over time, lead to serious consequences, including coronary heart disease, liver damage, retinopathy, nephropathy, strokes, and peripheral nephropathy [4]. α-Amylase and α-glucosidase are key enzymes involve in the breakdown and intestinal absorption of carbohydrates, respectively. Inhibition of these enzymes hampers blood glucose level increases after consumption of carbohydrates and can be an important strategy in the management of non-insulin-dependent diabetes mellitus (NIDDM) [5]. α-Amylases are distributed across various organisms and show diverse substrate specificities, while possessing a common topology formed by Molecules 2019, 24, 2342; doi:10.3390/molecules24122342 www.mdpi.com/journal/molecules Molecules 2019, 24, 2342 2 of 20 three domains, one of which being a typical α-β barrel. Inhibition of insects’ α-amylase is a proposed cropMolecules protection 2019,method. 24, x FOR PEER On theREVIEW other hand, inhibition of mammalian α-amylase is a proven therapeutic2 of 20 approach in diabetes and related disorders [6]. As diabetes affects about 5% of the global population, the managementcrop protection of method. diabetes On without the other any hand, side effinhibitionects is still of amammalian challenge toα-amylase the medical is a proven community, and thetherapeutic investigation approach on in agents diabetes for and this related purpose disorders has [6]. become As diabetes more affects important about and5% of researchers the global are population, the management of diabetes without any side effects is still a challenge to the medical competing to find the new effective and safe therapeutic agents for the treatment of diabetes [7–12]. community, and the investigation on agents for this purpose has become more important and Benzofuran and its analogues are important core structures for drug discovery, showing excellent researchers are competing to find the new effective and safe therapeutic agents for the treatment of pharmacologicaldiabetes [7–12]. activity like antiviral [13], anticancer [14], anti-inflammatory [15], antihyperlipidemic [16], anti-Alzheimer’sBenzofuran [17], and anticonvulsant its analogues [18 are], antitubercular important core [19 ],structures CNS regulatory for drug [20 discovery,], analgesic showing [21], enzyme inhibitionexcellent [22 ,23pharmacological], antipyretic activities activity [ 24like]. antiviral [13], anticancer [14], anti-inflammatory [15], antihyperlipidemicOn the other hand [16], spiroheterocyclic anti-Alzheimer’s compounds [17], anticonvulsant based on the [18], oxindole antitubercular scaffold have[19], gainCNS much attention,regulatory as they [20], exhibit analgesic pharmaceutical [21], enzyme inhibition activity [22,23], which antipyretic makes them activities promising [24]. lead compounds for drug discovery.On the other Numerous hand spiroheterocyclic biological activities compounds have ba beensed on reported the oxindole for these scaffold compounds, have gain much including anti-inflammatory,attention, as they antitumor exhibit pharmaceutical (as tyrosine kinase activity inhibitors), which makes antiviral, them promising antibacterial, lead compounds DMD2-p53 for protein drug discovery. Numerous biological activities have been reported for these compounds, including interaction inhibitory, and local anaesthetic activities [25–35]. One approach to discovering new drugs anti-inflammatory, antitumor (as tyrosine kinase inhibitors), antiviral, antibacterial, DMD2-p53 is to combine different pharmacophores like benzofuran, pyrrolidine, thiazolidine and spiroxindole protein interaction inhibitory, and local anaesthetic activities [25–35]. One approach to discovering systemsnew intodrugs one is to hybrid combine target different molecule pharmacophores and then like study benzofuran, the biological pyrrolidine, activity. thiazolidine In continuation and of ourspiroxindole research programsystems into to findone hybrid novel pharmaceuticaltarget molecule and agents, then study we now the describebiological theactivity. synthesis In of oxindolecontinuation/benzofuran of our/pyrrolidine research program/thiazolidine to find analogues novel pharmaceutical as new potential agents,α-amylase, we now and describeα-glucosidase the inhibitorssynthesis Figure of oxindole/benzofuran/pyrrolidine/thiazolidine1. analogues as new potential α-amylase, and α- glucosidase inhibitors. FigureFigure 1. Representative 1. Representative examples examples of of spirooxindoles, spirooxindoles, benzo[ benzo[b]furanb]furan scaffolds, scaffolds, acarbose acarbose as standard as standard drug anddrug our and designed our designed compounds. compounds. 2. Results2. Results Synthesis2.1. Synthesis of Compounds of Compounds5a–r 5a-r EquimolarEquimolar amounts amounts of of benzofuran-based benzofuran-based chalcones 2a-f2a–f werewere reacted reacted with with substituted substituted isatins isatins 2a–c2a-cand and heterocyclic heterocyclic amino amino acidsacids 4a,b4a,b inin the the presence presence of MeOH of MeOH as a solvent as a solvent to give tocycloadduct give cycloadduct in a in aone pot pot reaction reaction [36 [–3639]– 39(Scheme] (Scheme 1). After1). Aftercompletion completion of the reaction of the either reaction the cycloadduct either the cycloadductproduct productprecipitated precipitated (just (justsimple simple filtration filtration being beingneeded, needed, followed followed by washing by washing with 1 mL with of MeOH) 1 mL of or MeOH) the or solvent was removed and the crude product subjected to column chromatography for purification to the solvent was removed and the crude product subjected to column chromatography for purification give the target compounds (Table 1). to give the target compounds (Table1). Molecules 2019, 24, 2342 3 of 20 Molecules 2019, 24, x FOR PEER REVIEW 3 of 20 Molecules 2019, 24, x FOR PEER REVIEW 3 of 20 MoleculesMolecules 2019 2019, ,24 24, ,x x FOR FOR PEER PEER REVIEW REVIEW 33 ofof 2020 Scheme 1. The synthesized compounds 5a–r. SchemeScheme 1. The 1. synthesizedThe synthesized compounds compounds 5a-r. 5a-r. SchemeScheme 1.1. TheThe synthesizedsynthesized compoundscompounds 5a-r.5a-r. Table 1. Synthesized pirooxindoles and benzo[b]furan scaffolds 5a–r and their biological activity. Table 1. Synthesized pirooxindoles and benzo[b]furan scaffolds 5a-r and their biological activity Table 1. SynthesizedTableTable 1.1. SynthesizedSynthesized pirooxindoles pirooxindolespirooxindoles and benzo[ andand benzo[benzo[b]furanbb]furan]furan scaffolds scaffoldsscaffolds 5a-r 5a-r5a-r and andand their their biologicalbiological activityactivity activity α-Amylase α-Glucosidase α-Amylase α-Glucosidase # Compound α -Amylase α-Glucosidase α-Amylase α-Glucosidase # Compound α -Amylaseα -Amylase α-Glucosidaseα-Glucosidasea Selectivityα-Amylase-Amylaseb Selectivity α-Glucosidaseα-Glucosidasec # Compound α -AmylaseIC50 (µM SD)α-Glucosidasea
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