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Research Article

Novel Benzimidazole Derivatives as Effective Inhibitors of Prolyl Oligopeptidase: Synthesis, in Vitro and in Silico Analysis

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Pages 43-58 | Received 10 Sep 2023, Accepted 10 Nov 2023, Published online: 06 Dec 2023

References

  • Venäläinen JI , Juvonen RO , Männistö PT . Evolutionary relationships of the prolyl oligopeptidase family enzymes. Eur. J. Biochem. 271(13), 2705–2715 (2004).
  • Svarcbahs R , Julku U , Kilpeläinen T , Kyyrö M , Jäntti M , Myöhänen TT . New tricks of prolyl oligopeptidase inhibitors – a common drug therapy for several neurodegenerative diseases. Biochem. Pharmacol. 161, 113–120 (2019).
  • Sauer U , Eikmanns BJ . The PEP–pyruvate–oxaloacetate node as the switch point for carbon flux distribution in bacteria: we dedicate this paper to Rudolf K Thauer, Director of the Max-Planck-Institute for Terrestrial Microbiology in Marburg, Germany, on the occasion of his 65th birthday. FEMS Microbiol. Rev. 29(4), 765–794 (2005).
  • Ali H , Ullah K , Siddiqui H et al. Chemical constituents from Parrotia persica – structural derivatization and their potential prolyl endopeptidase inhibition activity. Bioorg. Chem. 96, 103526 (2020).
  • Zolotov NN , Schepetkin IA , Voronina TA et al. Therapeutic effect of novel cyanopyrrolidine-based prolyl oligopeptidase inhibitors in rat models of amnesia. Front. Chem. 9, 780958 (2021).
  • Song X-Q , Li Q , Zhang J . A double-edged sword: DLG5 in diseases. Biomed. Pharmacother. 162, 114611 (2023).
  • Malek M , Wawrzyniak AM , Koch P et al. Inositol triphosphate-triggered calcium release blocks lipid exchange at endoplasmic reticulum–Golgi contact sites. Nat. Commun. 12(1), 2673 (2021).
  • Wadhawan M , Ahmad F , Yadav S , Rathaur S . Proteomic analysis reveals differential protein expression induced by inhibition of prolyl oligopeptidase in filarial parasites. Protein J. 41(6), 613–624 (2022).
  • Alam A , Ali M , Rehman NU et al. Bio-oriented synthesis of novel (S)-flurbiprofen clubbed hydrazone schiff’s bases for diabetic management: in vitro and in silico studies. Pharmaceuticals 15(6), 672 (2022).
  • Tatum LA , Su X , Aprahamian I . Simple hydrazone building blocks for complicated functional materials. Acc. Chem. Res. 47(7), 2141–2149 (2014).
  • Yao X , Zhang R , Lv B et al. Design, synthesis and biological evaluation of thiazole and imidazo [1, 2-a] pyridine derivatives containing a hydrazone substructure as potential agrochemicals. Advanced Agrochem. 2(2), 154–162 (2023).
  • Jabeen M . A comprehensive review on analytical applications of hydrazone derivatives. Journal of the Turkish Chemical Society Section A: Chemistry 9(3), 663–698 (2022).
  • Sharma P , Sharma D , Sharma A et al. Hydrazone comprising compounds as promising anti-infective agents: chemistry and structure–property relationship. Mater. Today Chem. 18, 100349 (2020).
  • Ahmad S , Khan M , Shah MIA et al. Synthetic transformation of 2-{2-fluoro [1, 1′-biphenyl]-4-yl} propanoic acid into hydrazide–hydrazone derivatives: in vitro urease inhibition and in silico study. ACS Omega 7(49), 45077–45087 (2022).
  • Su X , Aprahamian I . Hydrazone-based switches, metallo-assemblies and sensors. Chem. Soc. Rev. 43(6), 1963–1981 (2014).
  • Zhou J , Guo T , Zhou L et al. The ferroptosis signature predicts the prognosis and immune microenvironment of nasopharyngeal carcinoma. Sci. Rep. 13(1), 1861 (2023).
  • Yang Z , Li P , Gan X . Novel pyrazole-hydrazone derivatives containing an isoxazole moiety: design, synthesis, and antiviral activity. Molecules 23(7), 1798 (2018).
  • Li L , Wang S , Zhou W . Balance cell apoptosis and pyroptosis of caspase-3-activating chemotherapy for better antitumor therapy. Cancers 15(1), 26 (2022).
  • Sridhar P , Alagumuthu M , Arumugam S , Reddy SR . Synthesis of quinoline acetohydrazide-hydrazone derivatives evaluated as DNA gyrase inhibitors and potent antimicrobial agents. RSC Adv. 6(69), 64460–64468 (2016).
  • Parlar S , Erzurumlu Y , Ilhan R , Ballar Kırmızıbayrak P , Alptüzün V , Erciyas E . Synthesis and evaluation of pyridinium-hydrazone derivatives as potential antitumoral agents. Chem. Biol. Drug Des. 92(1), 1198–1205 (2018).
  • Khan M , Ahad G , Manaf A et al. Synthesis, in vitro urease inhibitory activity, and molecular docking studies of (perfluorophenyl) hydrazone derivatives. Med. Chem. Res. 28, 873–883 (2019).
  • Shahab N , Kong D , Ali M et al. Novel polyhydroquinoline Schiff’s base derivatives: synthesis, characterization, in vitro α-glucosidase inhibitory, and molecular docking studies. Research on Chemical Intermediates 1–24 (2023).
  • Akdağ K , Ünal G , Tok F , Arıcıoğlu F , Temel HE , Kaymakcıoğlu-Koçyiğit B . Synthesis and biological evaluation of some new hydrazone derivatives bearing pyrimidine ring as analgesic and anti-inflammatory agents. Acta Pol. Pharm. 75(5), 1147–1159 (2018).
  • Talab F , Ullah S , Alam A et al. Bio-oriented synthesis of novel polyhydroquinoline derivatives as α-glucosidase inhibitor for management of diabetes. ACS Omega 8(7), 6234–6243 (2023).
  • Liu Z , Fan B , Zhao J , Yang B , Zheng X . Benzothiazole derivatives-based supramolecular assemblies as efficient corrosion inhibitors for copper in artificial seawater: formation, interfacial release and protective mechanisms. Corros. Sci. 212, 110957 (2023).
  • Kalidhar U , Kaur A . An overview on some benzimidazole and sulfonamide derivatives with anti-microbial activity. Res. J. Pharm. Biol. Chem. Sci. 2, 1116–1135 (2011).
  • Pathare B , Bansode T . Biological active benzimidazole derivatives. Results Chem. 3, 100200 (2021).
  • Li J-D , Wu J , Zhao Y et al. Phenotypic spectrum of idiopathic hypogonadotropic hypogonadism patients with CHD7 variants from a large Chinese cohort. J. Clin. Endocrinol. Metab. 105(5), 1515–1526 (2020).
  • Walia R , Hedaitullah M , Naaz SF , Iqbal K , Lamba H . Benzimidazole derivatives – an overview. Int. J. Res. Pharm. Chem. 1(3), 565–574 (2011).
  • Devivar RV , Kawashima E , Revankar GR et al. Benzimidazole ribonucleosides: design, synthesis, and antiviral activity of certain 2-(alkylthio)-and 2-(benzylthio)-5, 6-dichloro-1-(beta.-D-ribofuranosyl) benzimidazoles. J. Med. Chem. 37(18), 2942–2949 (1994).
  • Gellis A , Kovacic H , Boufatah N , Vanelle P . Synthesis and cytotoxicity evaluation of some benzimidazole-4, 7-diones as bioreductive anticancer agents. Eur. J. Med. Chem. 43(9), 1858–1864 (2008).
  • Bariwal J , Shah A , Kathiravan M , Somani R , Jagtap J , Jain K . Synthesis and antiulcer activity of novel pyrimidylthiomethyl-and pyrimidylsulfinylmethyl benzimidazoles as potential reversible proton pump inhibitors. Indian Journal of Pharmaceutical Education and Research 42(3), 225–231 (2008).
  • Alagöz Z , Kus C , Coban T . Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1, 1, 4, 4-tetramethyl-1, 2, 3, 4-tetrahydro-naphthalene fragments. J. Enzyme Inhib. Med. Chem. 20(4), (2005).
  • Vinodkumar R , Vaidya SD , Kumar BVS , Bhise UN , Bhirud SB , Mashelkar UC . Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2 [4-(4, 4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. Eur. J. Med. Chem. 43(5), 986–995 (2008).
  • Khan A , Waqas M , Khan M , Halim SA , Rehman NU , Al-Harrasi A . Identification of novel prolyl oligopeptidase inhibitors from resin of Boswellia papyrifera (Del.) Hochst. and their mechanism: virtual and biochemical studies. Int. J. Biol. Macromol. 213, 751–767 (2022).
  • Trott O , Olson AJ . AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31(2), 455–461 (2010).
  • Fülöp V , Szeltner Z , Polgár L . Catalysis of serine oligopeptidases is controlled by a gating filter mechanism. EMBO Rep. 1(3), 277–281 (2000).
  • Nehra N , Tittal RK , Ghule VD . 1, 2, 3-Triazoles of 8-hydroxyquinoline and HBT: synthesis and studies (DNA binding, antimicrobial, molecular docking, ADME, and DFT). ACS Omega 6(41), 27089–27100 (2021).
  • Waring MJ . Defining optimum lipophilicity and molecular weight ranges for drug candidates – molecular weight dependent lower log D limits based on permeability. Bioorg. Med. Chem. Lett. 19(10), 2844–2851 (2009).
  • Lipinski CA , Lombardo F , Dominy BW , Feeney PJ . Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 64, 4–17 (2012).

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