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Research Article

Design, Synthesis and Bio-Evaluation of Indolin-2-Ones As Potential Antidiabetic Agents

, ORCID Icon, ORCID Icon, , , , ORCID Icon, , , & ORCID Icon show all
Pages 25-42 | Received 02 Aug 2022, Accepted 05 Dec 2022, Published online: 16 Jan 2023

References

  • Chen L , MaglianoDJ , ZimmetPZ. The worldwide epidemiology of Type 2 diabetes mellitus – present and future perspectives. Nat. Rev. Endocrinol.8(4), 228–236 (2012).
  • Munhoz A , FrodeTS. Isolated compounds from natural products with a potential antidiabetic activity – a systematic review. Curr. Diabetes Rev.14(1), 36–106 (2018).
  • Sun X , YuW , HuC. Genetics of Type 2 diabetes: insights into the pathogenesis and its clinical application. Biomed. Res. Int.2014, 926713 (2014).
  • Kaul N , AliS. Genes, genetics, and environment in Type 2 diabetes: implication in personalized medicine. DNA Cell Biol.35, 1–12 (2016).
  • Gruss SM , NhimK , GreggE , BellM , LumanE , AlbrightA. Public health approaches to Type 2 diabetes prevention: the US National Diabetes Prevention Program and beyond. Curr. Diabetes Rep.19(9), 1–11 (2019).
  • Elosta A , SlevinM , RahmanK , AhmedN. Aged garlic has more potent antiglycation and antioxidant properties compared to fresh garlic extract in vitro. Sci. Rep.7(1), 1–9 (2017).
  • Kahn SE , CooperME , DelPrato S. Pathophysiology and treatment of Type 2 diabetes: perspectives on the past, present, and future. Lancet383(9922), 1068–1083 (2014).
  • Kajaria D , RanjanaJT , TripathiYB , TiwariS. In-vitro α-amylase and glycosidase inhibitory effect of ethanolic extract of antiasthmatic drug – Shirishadi. J. Adv. Pharm. Technol. Res.4(4), 206 (2013).
  • Ali M , KhanKM , SalarUet al. Synthesis, in vitro, α-glucosidase inhibitory activity, and in silico study of (E)-thiosemicarbazones and (E)-2-(2-(arylmethylene)hydrazinyl)-4-arylthiazole derivatives. Mol. Divers.22, 841–861 (2018).
  • Asghari S , Hosseinzadeh-AttarMJ , AlipoorE , SehatM , Mohajeri-TehraniMR. Effects of zinc supplementation on serum adiponectin concentration and glycemic control in patients with Type 2 diabetes. J. Trace Elem. Med. Biol.55, 20–25 (2019).
  • Liu H , JavaheriA , GodarRJet al. Intermittent fasting preserves beta-cell mass in obesity-induced diabetes via the autophagy-lysosome pathway. Autophagy13(11), 1952–1968 (2017).
  • Artasensi A , PedrettiA , VistoliG , FumagalliL. Type 2 diabetes mellitus: a review of multi-target drugs. Molecules25(8), 1987 (2020).
  • Da Silva JF , GardenSJ , PintoAC. The chemistry of isatins: a review from 1975 to 1999. J. Braz. Chem. Soc.12(3), 273–324 (2001).
  • Grewal AS . Isatin derivatives with several biological activities. Int. J. Pharm. Res.6(1), 1–7 (2014).
  • Pawar VS , LokwaniDK , BhandariSVet al. Design, docking study and ADME prediction of isatin derivatives as anti-HIV agents. Med. Chem. Res.20, 370–380 (2011).
  • Jarrahpour A , SheikhJ , ElMounsi I , JunejaH , HaddaTB. Computational evaluation and experimental in vitro antibacterial, antifungal, and antiviral activity of bis-Schiff bases of isatin and its derivatives. Med. Chem. Res.22, 1203–1211 (2013).
  • Pandeya SN , SmithaS , JyotiM , SridharSK. Biological activities of isatin and its derivatives. Acta Pharm.55(1), 27–46 (2005).
  • Cheke RS , PatilVM , FirkeSDet al. Therapeutic outcomes of isatin and its derivatives against multiple diseases: recent developments in drug discovery. Pharmaceuticals15(3), 272 (2022).
  • Khan KM , MughalUR , KhanA , NazF , PerveenS , ChoudharyMI. N-Aroylated isatins: antiglycation activity. Lett. Drug Des. Discov.7(3), 188 (2010).
  • Chiyanzu I , ClarksonC , SmithPJet al. Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. Bioorg. Med. Chem.13(9), 3249–3261 (2005).
  • Raj R , SinghP , SinghP , GutJ , RosenthalPJ , KumarV. Azide-alkyne cycloaddition en route to 1H-1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: synthesis and antimalarial evaluation. Eur. J. Med. Chem.62, 590–596 (2013).
  • Lashgari N , ZiaraniGM. Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions. Arkivoc2012(1), 277–300 (2012).
  • Kakkar R . Isatin and its derivatives: a survey of recent syntheses, reactions, and applications. Med. Chem. Comm.10(3), 351–368 (2019).
  • Yaylı N , KılıçG , KahrimanNet al. Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous. Bioorg. Chem.115, 105183 (2021).
  • Akhtar J , KhanAA , AliZ , HaiderR , YarMS. Structure–activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities. Eur. J. Med. Chem.125, 143–189 (2017).
  • Kerru N , GummidiL , MaddilaS , GanguKK , JonnalagaddaSB. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules25, 1909 (2020).
  • Derosa G , MaffioliP. α-Glucosidase inhibitors and their use in clinical practice. Arch. Med. Sci.8(5), 899–906 (2012).
  • Hameed S , KhanKM , TaslimiPet al. Evaluation of synthetic 2-aryl quinoxaline derivatives as α-amylase, α-glucosidase, acetylcholinesterase, and butyrylcholinesterase inhibitors. Int. J. Biol. Macromol.211, 653–668 (2022).
  • Wahid S , JahangirS , VersianiMAet al. Biology-oriented drug synthesis of nitrofurazone derivatives: their α-glucosidase inhibitory activity and molecular docking studies. Arab. J. Chem.15(6), 103806 (2022).
  • Solangi M , Kanwal , KhanKMet al. Indole acrylonitriles as potential anti-hyperglycemic agents: synthesis, α-glucosidase inhibitory activity, and molecular docking studies. Bioorg. Med. Chem.28(21), 115605 (2020).
  • Ali I , RafiqueR , KhanKMet al. Potent α-amylase inhibitors and radical (DPPH and ABTS) scavengers based on benzofuran-2-yl (phenyl) methanone derivatives: syntheses, in vitro, kinetics, and in silico studies. Bioorg. Chem.104, 104238 (2020).
  • Saleem F , Kanwal , KhanKMet al. Dicyanoanilines as potential and dual inhibitors of α-amylase and α-glucosidase enzymes: synthesis, characterization, in vitro, in silico, and kinetics studies. Arab. J. Chem.15(3), 103651 (2022).
  • Rahim F , MalikF , UllahHet al. Isatin-based Schiff bases as inhibitors of α-glucosidase: synthesis, characterization, in vitro evaluation and molecular docking studies. Bioorg. Chem.60, 42–48 (2015).
  • Khan KM , KhanM , AliMet al. Synthesis of bis-Schiff bases of isatins and their antiglycation activity. Bioorg. Med. Chem.17(22), 7795–7801 (2009).
  • Arivazhagana R , ChigurupatiS , PrakasamaA. Exploring molecular structure, spectral features, electronic properties, and molecular docking of a novel biologically active heterocyclic compound 4-phenylthiosemicarbazide. J. Mol. Struct.1232, 129956 (2021).
  • Solangi M , Kanwal , KhanKMet al. Isatin thiazoles as antidiabetic: synthesis, in vitro enzyme inhibitory activities, kinetics, and in silico studies. Arch. Pharm.355, e2100481 (2022).
  • Jamil W , SolangiS , AliM , KhanKM , TahaM , KhuhawarMY. Syntheses, characterization, in vitro antiglycation and DPPH radical scavenging activities of isatin salicylhydrazidehydrazone and its Mn (II), Co (II), Ni (II), Cu (II), and Zn (II) metal complexes. Arab. J. Chem.12(8), 2262–2269 (2019).
  • Shingade SG , BariSB , WaghmareUB. Synthesis and antimicrobial activity of 5-chloroindoline-2,3-dione derivatives. Med. Chem. Res.21, 1302–1312 (2012).
  • Nikalje AP , AnsariA , BariS , UgaleV. Synthesis, biological activity, and docking study of novel isatin coupled thiazolidin-4-one derivatives as anticonvulsants. Arch. Pharm.348, 433–445 (2015).
  • Gholamzadeh P , ZiaraniGM , BadieiA. Application of SBA-Pr-SO3H in the green synthesis of isatinhydrazone derivatives: characterization, UV-vis investigation, and computational studies. J. Chil. Chem. Soc.61(2), 2935–2939 (2016).
  • Chigurupati S , AlharbiFS , AlmahmoudSet al. Molecular docking of phenolic compounds and screening of antioxidant and antidiabetic potential of Olea europaea L. ethanolic leaves extract. Arab. J. Chem.14(11), 103422 (2021).
  • Aroua LM , AlmuhaylanHR , AlminderejFMet al. A facile approach synthesis of benzoylaryl benzimidazole as potential α-amylase and α-glucosidase inhibitor with antioxidant activity. Bioorg. Chem.114, 105073 (2021).
  • Shamim S , KhanKM , UllahNet al. Synthesis and screening of (E)-3-(2-benzylidenehydrazinyl)-5,6-diphenyl-1,2,4-triazine analogs as novel dual inhibitors of α-amylase and α-glucosidase. Bioorg. Chem.101, 103979 (2020).
  • Lukomskaya IS , VoznyiYV , LanskayaIM , PodkidishevaEI. Use of β-maltosides (p-nitrophenyl-β-d-maltoside, 2-chloro-4-nitrophenyl-β-d-maltoside, and 4-methylumbelliferyl-β-d-maltoside) as substrates for the assay of neutral α-glucosidase from human kidney and urine. Clin. Chim. Acta244(2), 145–154 (1996).
  • Saleem F , Kanwal , KhanKMet al. Synthesis of azachalcones, their α-amylase, α-glucosidase inhibitory activities, kinetics, and molecular docking studies. Bioorg. Chem.106, 104489 (2021).
  • Babatunde O , HameedS , SalarUet al. Dihydroquinazolin-4 (1H)-one derivative as novel and potential lead for diabetic management. Mol. Divers.26, 849–868 (2021).
  • Chigurupati S . Antidiabetic and antioxidant potential of Duriozibethinus murr. leaves ethanolic extract. Indian J. Exp. Biol.59(2), 102–110 (2021).
  • Chemical Computing Group Inc. Molecular operating environment (MOE) (2016).
  • Carreiro EP , LouroP , AdrianoGet al. 3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: inhibition of rat intestinal α-glucosidase. Bioorg. Chem.54, 81–88 (2014).
  • Rahim F , TahaM , UllahHet al. Synthesis of new aryl hydrazide bearing Schiff bases/thiazolidinone: α-amylase, urease activities, and their molecular docking studies. Bioorg. Chem.91, 103112 (2019).
  • Malak N , NiazS , WadoodAet al. In silico approaches to develop herbal acaricides against R. (Boophilus) microplus and in vitro anti-tick activities of selected medicinal plants. Saudi J. Biol. Sci.29(6), 103302 (2022).
  • Ramírez-Escudero M , Gimeno-PérezM , GonzálezBet al. Structural analysis of β-fructofuranosidase from Xanthophyllomyces dendrorhous reveals unique features and the crucial role of N-glycosylation in oligomerization and activity. J. Biol. Chem.291(13), 6843–6857 (2016).

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