7-Amino-3,4-dihydro-1H-quinolin-2-one, a compound similar to the substituted coumarins, inhibits -carbonic anhydrases without hydrolysis of the lactam ring

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 30, Issue 5, 2015, Pages 773-777

  Vullo, Daniela ^a   Isik, Semra ^b   Bozdag, Murat ^a   Carta, Fabrizio ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b BALIKESIR UNIVERSITY   (Turkey)

Author keywords

Carbonic anhydrase; coumarin; inhibitor; isoform selectivity; lactam; lactone; quinolon 2 one

Indexed keywords

4 METHYL 7 AMINOCOUMARIN; 7 AMINO 3,4 DIHYDRO 1H QUINOLIN 2 ONE; ACETAZOLAMIDE; ALPHA CARBONATE DEHYDRATASE; AMINOQUINOLINE DERIVATIVE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE III; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE V; CARBONATE DEHYDRATASE VI; CARBONATE DEHYDRATASE VII; CARBONATE DEHYDRATASE XII; CARBONATE DEHYDRATASE XIII; CARBONATE DEHYDRATASE XIV; COUMARIN DERIVATIVE; ISOENZYME; LACTAM DERIVATIVE; LACTONE; UNCLASSIFIED DRUG; 7-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE; LACTAM; QUINOLONE DERIVATIVE;

ARTICLE; CATALYSIS; CONCENTRATION RESPONSE; DRUG HYDROLYSIS; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; INCUBATION TIME; INHIBITION CONSTANT; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HYDROLYSIS; METABOLISM; SYNTHESIS;

AMINOQUINOLINES; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; COUMARINS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDROLYSIS; ISOENZYMES; LACTAMS; MOLECULAR STRUCTURE; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84940728448     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2014.970185     Document Type: Article

References (62)

1. Alterio V, Di Fiore A, D'Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421-68.
2. Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759-72.
3. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Disc 2008;7:168-81.
4. 2 capture. J Enzyme Inhib Med Chem 2013;28:229-30.
5. Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nature Rev Drug Discovery 2011;10:767-77.
6. Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008-2013). Expert Opin Ther Pat 2013;23:737-49.
7. Rummer JL, McKenzie DJ, Innocenti A, et al. Root effect hemoglobin may have evolved to enhance general tissue oxygen delivery. Science 2013;340:1327-9.
8. Capasso C, Supuran CT. Sulfa and trimethoprim-like drugs-antimetabolites acting as carbonic anhydrase, dihydropteroate synthase and dihydrofolate reductase inhibitors. J Enzyme Inhib Med Chem 2014;29:379-87.
9. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-74.
10. Harju AK, Bootorabi F, Kuuslahti M, et al. Carbonic anhydrase III: a neglected isozyme is stepping into the limelight. J Enzyme Inhib Med Chem 2013;28:231-9.
11. Çavdar H, Ekinci D, Talaz O, et al. α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters. J Enzyme Inhib Med Chem 2012;27:148-54.
12. De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793-810.
13. Durdagi S, Scozzafava G, Vullo D, et al. Inhibition of mammalian carbonic anhydrases I-XIV with grayanotoxin III: solution and in silico studies. J Enzyme Inhib Med Chem 2014;29:469-75.
14. Bilginer S, Unluer E, Gul HI, et al. Carbonic anhydrase inhibitors. Phenols incorporating 2- or 3-pyridyl-ethenylcarbonyl and tertiary amine moieties strongly inhibit Saccharomyces cerevisiae β-carbonic anhydrase. J Enzyme Inhib Med Chem 2014;29:495-9.
15. 18F-labeled carbonic anhydrase IX inhibitors for imaging with positron emission tomography. J Enzyme Inhib Med Chem 2014;29:249-55.
16. Smith KS, Jakubzick C, Whittam TS, Ferry JG. Carbonic anhydrase is an ancient enzyme widespread in prokaryotes. Proc Natl Acad Sci USA 1999;96:15184-9.
17. Xu Y, Feng L, Jeffrey PD, et al. Structure and metal exchange in the cadmium carbonic anhydrase of marine diatoms. Nature 2008;452:56-61.
18. Supuran CT. Bacterial carbonic anhydrases as drug targets: towards novel antibiotics? Front Pharmacol 2011;2:34. doi: 10.3389/fphar.2011.00034.
19. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-89.
20. Ebbesen P, Pettersen EO, Gorr TA, et al. Taking advantage of tumor cell adaptations to hypoxia for developing new tumor markers and treatment strategies. J Enzyme Inhib Med Chem 2009;24:1-39.
21. Del Prete S, Vullo D, Fisher GM, et al. Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum - The η-carbonic anhydrases. Bioorg Med Chem Lett 2014;24:4389-96.
22. 2): a patent review 2008-2012. Expert Opin Ther Pat 2012;22:747-58.
23. Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012;27:138-47.
24. Ekinci D, Karagoz L, Ekinci D, et al. Carbonic anhydrase inhibitors: in vitro inhibition of α isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids. J Enzyme Inhib Med Chem 2013;28:283-8.
25. Carta F, Supuran CT, Scozzafava A. Novel therapies for glaucoma: a patent review 2007-2011. Expert Opin Ther Pat 2012;22:79-88.
26. Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: A patent review. Expert Opin Ther Pat 2013;23:705-16.
27. (a) Supuran CT, Maresca A, Gregáň F, Remko M. Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII. J Enzyme Inhib Med Chem 2013;28:289-93.
28. (b) Alp C, Maresca A, Alp NA, et al. Secondary/tertiary benzenesulfonamides with inhibitory action against the cytosolic human carbonic anhydrase isoforms I and II. J Enzyme Inhib Med Chem 2013;28:294-8.
29. Supuran CT. Carbonic anhydrase inhibitors: an editorial. Expert Opin Ther Pat 2013;23:677-9.
30. Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: A patent and literature review (2005-2013). Expert Opin Ther Pat 2013;23:681-91.
31. Supuran CT. Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs 2012;17:11-15.
32. Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat 2013;23:725-35.
33. Wilkinson BL, Bornaghi LF, Houston TA, et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 2007;50:1651-7.
34. Gieling RG, Parker CA, De Costa LA, et al. Inhibition of carbonic anhydrase activity modifies the toxicity of doxorubicin and melphalan in tumour cells in vitro. J Enzyme Inhib Med Chem 2013;28:360-9.
35. Capasso C, Supuran CT. Antiinfective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat 2013;23:693-704.
36. Del Prete S, De Luca V, Scozzafava A, et al. Biochemical properties of a new α-carbonic anhydrase from the human pathogenic bacterium Vibrio cholerae. J Enzyme Inhib Med Chem 2014;29:23-7.
37. Singh S, Supuran CT. 3D-QSAR CoMFA studies on sulfonamide inhibitors of the Rv3588c β-carbonic anhydrase from Mycobacterium tuberculosis and design of not yet synthesized new molecules. J Enzyme Inhib Med Chem 2014;29:449-55.
38. Maresca A, Vullo D, Scozzafava A, Supuran CT. Inhibition of the alpha- and beta-carbonic anhydrases from the gastric pathogen Helycobacter pylori with anions. J Enzyme Inhib Med Chem 2013;28:388-91.
39. Maresca A, Scozzafava A, Vullo D, Supuran CT. Dihalogenated sulfanilamides and benzolamides are effective inhibitors of the three β-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem 2013;28:384-7.
40. Maresca A, Carta F, Vullo D, Supuran CT. Dithiocarbamates strongly inhibit the beta-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem 2013;28:407-11.
41. Allouche F, Chabchoub F, Carta F, Supuran CT. Synthesis of aminocyanopyrazoles via a multi-component reaction and anticarbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms. J Enzyme Inhib Med Chem 2013;28:343-9.
42. Alp C, Özsoy S, Alp NA, et al. Sulfapyridine-like Benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI. J Enzyme Inhib Med Chem 2012;27:818-24.
43. Koz O, Ekinci D, Perrone A, et al. Analysis of saponins and phenolic compounds as inhibitors of α-carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2013;28:412-17.
44. Avram S, Milac AL, Carta F, Supuran CT. More effective dithiocarbamate derivatives inhibiting carbonic anhydrases, generated by QSAR and computational design. J Enzyme Inhib Med Chem 2013;28:350-9.
45. Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057-62.
46. Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335-44.
47. Touisni N, Maresca A, McDonald PC, et al. Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors. J Med Chem 2011;54:8271-7.
48. Maresca A, Supuran CT. Coumarins incorporating hydroxy- and chloro- moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg Med Chem Lett 2010;20:4511-14.
49. Maresca A, Scozzafava A, Supuran CT. 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range. Bioorg Med Chem Lett 2010;20:7255-8.
50. Carta F, Maresca A, Scozzafava A, Supuran CT. Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem 2012;20:2266-73.
51. Bonneau A, Maresca A, Winum JY, Supuran CT. Metronidazole-coumarin conjugates and 3-cyano-7-hydroxy-coumarin act as isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2013;28:397-401.
52. Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292-6.
53. 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.
54. Tanc M, Carta F, Bozdag M, et al. 7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors. Bioorg Med Chem 2013;21:4502-10.
55. Grandane A, Tanc M, Zalubovskis R, Supuran CT. Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem 2014;22:1522-8.
56. Grandane A, Tanc M, Zalubovskis R, Supuran CT. 6-Triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem Lett 2014;24:1256-60.
57. Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I - XIV). Bioorg Med Chem Lett 2008;18:1583-7.
58. Carta F, Temperini C, Innocenti A, et al. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem 2010;53:5511-22.
59. 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.
60. Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896-902.
61. Nishimori I, Minakuchi T, Morimoto K, et al. Carbonic anhydrase inhibitors. DNA cloning and inhibition studies of the α-carbonic anhydrase from Helicobacter pylori: a new target for developing sulfonamide and sulfamate gastric drugs. J Med Chem 2006;49:2117-26.
62. Supuran CT, Scozzafava A. Matrix metalloproteinases (MMPs). In: Smith HJ, Simons C, eds. Proteinase and peptidase inhibition: recent potential targets for drug development. London & New York: Taylor & Francis; 2002:35-61.