Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety

References

• Feng LS, Liu ML, Wang S, et al. Synthesis of naphthyridone derivatives containing 8-alkoxyimino-1,6-dizaspiro[3.4]octane scaffolds. Tetrahedron 2011;67:8264–70.
   Web of Science ®Google Scholar
• Hu YQ, Zhang S, Xu Z, et al. 4-Quinolone hybrids and their antibacterial activities. Eur J Med Chem 2017;141:335–45.
   PubMed Web of Science ®Google Scholar
• Panda SS, Ibrahim MA, Küçükbay H, et al. Synthesis and antimalarial bioassay of quinine–peptide conjugates. Chem Biol Drug Des 2013;82:361–6.
   PubMed Web of Science ®Google Scholar
• Katariya KD, Shah SR, Reddy D. Anticancer, antimicrobial activities of quinoline based hydrazone analogues: synthesis, characterization and molecular docking. Bioorg Chem 2020;94:103406.
   PubMed Web of Science ®Google Scholar
• Vullo D, Isik S, Bozdag M, et al. 7-Amino-3,4-dihydro-1H-quinolin-2-one, a compound similar to the substituted coumarins, inhibits α-carbonic anhydrases without hydrolysis of the lactam ring. J Enzyme Inhib Med Chem 2015;30:773–7.
   PubMed Web of Science ®Google Scholar
• Küçükbay FZ, Küçükbay H, Tanc M, Supuran CT. Synthesis and carbonic anhydrase inhibitory properties of amino acid – coumarin/quinolinone conjugates incorporating glycine, alanine and phenylalanine moieties. J Enzyme Inhib Med Chem 2016;31:1198–202.
   PubMed Web of Science ®Google Scholar
• Liu B, Li F, Zhou T, et al. Quinoline derivatives with potential activity against multidrug-resistant tuberculosis. J Heterocycl Chem 2018;55:1863–73.
   Web of Science ®Google Scholar
• Ibrahim MA, Hassanin HM, Abass M, Badran S. Synthesis of substituted quinolinone ketones derived with some five, six, and seven-membered heterocycles. J Turk Chem Soc 2016; 3:27–45.
   Google Scholar
• Cheng P, Zhang Q, Ma YB, et al. Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives. Bioorganic Med Chem Lett 2008;18:3787–9.
   PubMed Web of Science ®Google Scholar
• Meiring L, Petzer JP, Petzer A. A review of the pharmacological properties of 3,4-dihydro-2(1H)-quinolinones. Mini Rev Med Chem 2018;18:828–36.
   PubMed Web of Science ®Google Scholar
• Panda SS, Hall CD, Scriven E, Katritzky AR. Aminoacyl benzotriazolides: versatile reagents for the preparation of peptides and their mimetics and conjugates. Aldrichimica Acta 2014;46:43–58.
   Web of Science ®Google Scholar
• (a) Supuran CT. Exploring the multiple binding modes of inhibitors to carbonic anhydrases for novel drug discovery. Expert Opin Drug Discov in press.;
   Web of Science ®Google Scholar
  (b) Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016; 473:2023–32;
   PubMed Web of Science ®Google Scholar
  (c) Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin Drug Discov 2017;12:61–88;
   PubMed Web of Science ®Google Scholar
  (d) Nocentini A, Supuran CT. Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opin Drug Discov 2019; 14:1175–97.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81;
   PubMed Web of Science ®Google Scholar
  (b) Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77;
   PubMed Web of Science ®Google Scholar
  (c) Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60;
   PubMed Web of Science ®Google Scholar
  (d) Supuran CT. Carbonic anhydrases and metabolism. Metabolites 2018;8:25.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Briganti F, Menabuoni L, et al. Carbonic anhydrase inhibitors – Part 78. Synthesis of water-soluble sulfonamides incorporating β-alanyl moieties, possessing long lasting- intraocular pressure lowering properties via the topical route. Eur J Med Chem 2000;35:309–21;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT, Capasso C. An overview of the bacterial carbonic anhydrases. Metabolites 2017;7:56;
   PubMed Web of Science ®Google Scholar
  (c) Supuran CT, Capasso C. Biomedical applications of prokaryotic carbonic anhydrases. Expert Opin Ther Pat 2018;28:745–54;
   PubMed Web of Science ®Google Scholar
  (d) Supuran CT. Carbonic anhydrase inhibitors and their potential in a range of therapeutic areas. Expert Opin Ther Pat 2018;28:709–12.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Alterio V, Di Fiore A, et al. Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: three for the price of one. Med Res Rev 2018;38:1799–836;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs 2018;27:963–70;
   PubMed Web of Science ®Google Scholar
  (c) Nocentini A, Supuran CT. Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008–2018). Expert Opin Ther Pat 2018;28:729–40.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT. Applications of carbonic anhydrases inhibitors in renal and central nervous system diseases. Expert Opin Ther Pat 2018;28:713–21;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT, Altamimi ASA, Carta F. Carbonic anhydrase inhibition and the management of glaucoma: a literature and patent review 2013–2019. Expert Opin Ther Pat 2019;29:781–92;
   PubMed Web of Science ®Google Scholar
  (c) Supuran CT. The management of glaucoma and macular degeneration. Expert Opin Ther Pat 2019;29:745–7.
   PubMed Web of Science ®Google Scholar
• El Khatib M, Jauregui L, Tala SR, et al. Solution-phase synthesis of chiral O-acyl isodipeptides. Medchemcomm 2011;2:1087.
   Web of Science ®Google Scholar
• Bugday N, Kucukbay FFZ, Apohan E, et al. Synthesis and evaluation of novel benzimidazole conjugates incorporating amino acids and dipeptide moieties. Lett Org Chem 2017;14:198–206.
   Web of Science ®Google Scholar
• (a) Küçükbay H, Buğday N, Küçükbay FZ, et al. Bioorganic chemistry synthesis and carbonic anhydrase inhibitory properties of novel 4-(2-aminoethyl)benzenesulfonamide–dipeptide conjugates. Bioorg Chem 2019;83:414–23;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT. Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors? J Enzyme Inhib Med Chem 2018;33:485–95;
   PubMed Web of Science ®Google Scholar
  (c) Nocentini A, Bonardi A, Gratteri P, et al. Steroids interfere with human carbonic anhydrase activity by using alternative binding mechanisms. J Enzyme Inhib Med Chem 2018;33:1453–9.
   PubMed Web of Science ®Google Scholar
• (a) Buğday N, Küçükbay FZ, Küçükbay H, et al. Synthesis of novel dipeptide sulfonamide conjugates with effective carbonic anhydrase I, II, IX, and XII inhibitory properties. Bioorg Chem 2018;81:311–8;
   PubMed Web of Science ®Google Scholar
  (b) Innocenti A, Vullo D, Scozzafava A, et al. Carbonic anhydrase inhibitors. Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I–XIV). Bioorg Med Chem Lett 2008;18:1583–7;
   PubMed Web of Science ®Google Scholar
  (c) Innocenti A, Vullo D, Scozzafava A, et al. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I–XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem 2008;16:7424–8;
   PubMed Web of Science ®Google Scholar
  (d) Bayram E, Senturk M, Kufrevioglu OI, et al. In vitro effects of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg Med Chem 2008;16:9101–5.
   PubMed Web of Science ®Google Scholar
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73.
   PubMed Web of Science ®Google Scholar
• (a) Mincione F, Starnotti M, Menabuoni L, et al. Carbonic anhydrase inhibitors: 4-sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties. Bioorganic Med Chem Lett 2001;11:1787–91;
   PubMed Web of Science ®Google Scholar
  (b) Tars K, Vullo D, Kazaks A, et al. Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases. J Med Chem 2013;56:293–300;
   PubMed Web of Science ®Google Scholar
  (c) D'Ambrosio K, Carradori S, Monti SM, et al. Out of the active site binding pocket for carbonic anhydrase inhibitors. Chem Commun 2015;51:302–5;
   PubMed Web of Science ®Google Scholar
  (d) Güzel-Akdemir Ö, Angeli A, Demir K, et al. Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors. J Enzyme Inhib Med Chem 2018;33:1299–308.
   PubMed Web of Science ®Google Scholar
• (a) Del Prete S, Vullo D, De Luca V, et al. Biochemical characterization of recombinant β-carbonic anhydrase (PgiCAb) identified in the genome of the oral pathogenic bacterium Porphyromonas gingivalis. J Enzyme Inhib Med Chem 2015;30:366–70;
   PubMed Web of Science ®Google Scholar
  (b) Ammazzalorso A, Carradori S, Angeli A, et al. Fibrate-based N-acylsulphonamides targeting carbonic anhydrases: synthesis, biochemical evaluation, and docking studies. J Enzyme Inhib Med Chem 2019;34:1051–61.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorganic Med Chem 2007;15:4336–50;
   PubMed Web of Science ®Google Scholar
  (b) De Simone G, Supuran CT. (In)organic anions as carbonic anhydrase inhibitors. J Inorg Biochem 2012;111:117–29;
   PubMed Web of Science ®Google Scholar
  (c) Nocentini A, Supuran CT, Winum JY. Benzoxaborole compounds for therapeutic uses: a patent review (2010–2018). Expert Opin Ther Pat 2018;28:493–504.
   PubMed Web of Science ®Google Scholar
• (a) Maresca A, Vullo D, Scozzafava A, et al. Inhibition of the β-class carbonic anhydrases from Mycobacterium tuberculosis with carboxylic acids. J Enzyme Inhib Med Chem 2013;28:392–6;
   PubMed Web of Science ®Google Scholar
  (b) Köhler K, Hillebrecht A, Schulze Wischeler J, et al. Saccharin inhibits carbonic anhydrases: possible explanation for its unpleasant metallic aftertaste. Angew Chem Int Ed Engl 2007;46:7697–9.
   PubMed Web of Science ®Google Scholar
• (a) Scozzafava A, Passaponti M, Supuran CT, Gülçin I. Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII). J Enzyme Inhib Med Chem 2015;30:586–91;
   PubMed Web of Science ®Google Scholar
  (b) Pustenko A, Stepanovs D, Žalubovskis R, et al. 3H-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2017;32:767–75.
   PubMed Web of Science ®Google Scholar
• (a) Küçükbay H, Buğday N, Küçükbay FZ, et al. Synthesis and human carbonic anhydrase I, II, VA, and XII inhibition with novel amino acid–sulphonamide conjugates. J Enzyme Inhib Med Chem 2020;35:489–97;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT. Carbonic anhydrase activators. Future Med Chem 2018;10:561–73.
   PubMed Web of Science ®Google Scholar
• Yang J, Guo J, Yuan J. In vitro antioxidant properties of rutin. LWT – Food Sci Technol 2008;41:1060–6.
   Web of Science ®Google Scholar
• (a) Supuran C. Carbonic anhydrases an overview. Curr Pharm Des 2008;14:603–14;
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev Neurother 2015;15:851–6;
   PubMed Web of Science ®Google Scholar
  (c) Supuran CT. Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol 2016;12:423–31.
   PubMed Web of Science ®Google Scholar
• (a) Küçükbay FZ, Buğday N, Küçükbay H, et al. Synthesis, characterization and carbonic anhydrase inhibitory activity of novel benzothiazole derivatives. J Enzyme Inhib Med Chem 2016;31:1221–5;
   PubMed Web of Science ®Google Scholar
  (b) Alterio V, Esposito D, Monti SM, et al. Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2,4,6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor. J Enzyme Inhib Med Chem 2018;33:151–7.
   PubMed Web of Science ®Google Scholar
• Payaz DÜ, Küçükbay FZ, Küçükbay H, et al. Synthesis carbonic anhydrase enzyme inhibition and antioxidant activity of novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine moieties. J Enzyme Inhib Med Chem 2019;34:343–9.
   PubMed Web of Science ®Google Scholar