2-Amino-3-cyanopyridine derivatives as carbonic anhydrase inhibitors

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 2, 2013, Pages 305-310

  Ayvaz, Selçuk ^a   Çankaya, Murat ^b   Atasever, Ali ^c   Altuntas, Aliye ^a  

^a GAZI UNIVERSITY   (Turkey)

^b ERZINCAN UNIVERSITY   (Turkey)

^c ATATÜRK UNIVERSITY   (Turkey)

Author keywords

2 amino 3 cyanopyridines; 4 furyl; 4 thienyl; Carbonic anhydrase; Enzyme inhibition

Indexed keywords

AMINOPYRIDINE DERIVATIVE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; ISOPROTEIN; NITRILE;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ENZYMOLOGY; ERYTHROCYTE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINOPYRIDINES; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ERYTHROCYTES; HUMANS; MOLECULAR STRUCTURE; NITRILES; PROTEIN ISOFORMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891403878     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.639016     Document Type: Article

References (42)

1. Supuran CT. Carbonic anhydrase inhibition/activation: trip of a scientist around the world in the search of novel chemotypes and drug targets. Curr Pharm Des 2010;16:3233-3245.
2. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-3474.
3. Supuran CT. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Future Med Chem 2011;3:1165-1180.
4. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-181.
5. Xu Y, Feng L, Jeffrey PD, Shi Y, Morel FM. Structure and metal exchange in the cadmium carbonic anhydrase of marine diatoms. Nature 2008;452:56-61.
6. Burnell JN. (2000). Carbonic anhydrases of higher plants: An overview. In: Chegwidden, WR, Carter, ND, Edwards, YH (Eds.), The Carbonic Anhydrases. New Horizons. Basel: Birkhäuser Verlag, 501-518.
7. Forsman, C. (2000). Plant carbonic anhydrases: structure and mechanism. The Carbonic Anhydrases. New Horizons. Basel: Birkhäuser Verlag, 519-533.
8. Fukuzawa H, Tsuzuki M, Miyachi S. (2000). The Carbonic Anhydrases. New Horizons. Basel: Birkhäuser Verlag, 535-546.
9. Kozliak EI, Guilloton MB, Fuchs JA, Anderson PM. (2000)Bacterial carbonic anhydrases. New Horizons. Bassel: Birkhäuser Verlag, 547-565.
10. Zimmerman SA, Ferry JG. The β and g classes of carbonic anhydrase. Curr Pharm Des 2008;14:716-721.
11. Rowlett RS. Structure and catalytic mechanism of the ß-carbonic anhydrases. Biochim. Biophys 2010;1804:362-373.
12. Supuran CT, Scozzafava A, Conway J. (2004). Carbonic anhydrase? Its inhibitors and activators, Eds. Boca Raton, FL, USA: CRC Press, 1-376.
13. 2 hydration catalyzed by carbonic anhydrase. Biochem Biophys Res Commun 1982;108:1406-1412.
14. Tibell L, Forsman C, Simonsson I, Lindskog S. The inhibition of human carbonic anhydrase II by some organic compounds. Biochim Biophys Acta 1985;829;202-208.
15. Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A et al. Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057-3062.
16. Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT. Deciphering the mechanism of carbonic anhydrase inhibition with coumarines and thiocoumarines. J Med Chem 2010;53:335-344.
17. Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: The antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J Med Chem 2010;53:850-854
18. Carta F, Temperini C, Innocenti A, Scozzafava A, Kaila K, Supuran CT. Polyamines inhibit carbonic anhydrases by anchoring to the zinccoordinated water molecule. J Med Chem 2010;53:5511-5522.
19. Rami M, Winum JY, Innocenti A, Montero JL, Scozzafava A, Supuran CT. Carbonic anhydrese inhibitors: Copper (II) complexes of polyamino-polycarboxyamido aromatic/heterocyclic sulfonamides are very potent inhibitors of tumor-associated isoforms IX and XII. Bioorg Med Chem Lett 2008;18(2):836-841.
20. Supuran CT. Carbonic anhydrase inhibition with natural products: Novel chemotypes and inhibition mechanisms. Mol Divers 2011;15(2):305-316.
21. Davis RA, Innocenti A, Poulsen SA, Supuran CT. Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library. Bioorg Med Chem 2010;18:14-18.
22. Abbate F, Casini A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide. Bioorg Med Chem Lett 2004;14:2357-2361.
23. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-189.
24. Moussa HH, Chabaka LM, Zaki D. Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo-4- phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues. Egypt J Chem 1983;26:469-477.
25. Manna F, Chimenti F, Bolasco A, Bizzarri B, Filippelli W, Fiilppelli A, Gagliardi L. Eur. Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines. J Med Chem 1999;34:245-254.
26. Thapa P, Karki R, Thapa U, Jahng Y, Jung MJ, Nam JM et al. 2-Thienyl- 4-furyl-6-aryl pyridine derivatives: synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study. Bioorg Med Chem 2010;18:377-386.
27. Doe K, Avasthi K, Pratap R, Bakuni DS, Joshi MN. Synthes?s of 2,4-bis(methylthio)-5,7-disubst?tuted-7H-pyrrolo-(2,3-D) pyrimidines and their biological-activity. Indian J Chem Sect B 1991;30:499-506.
28. Altundas A, Ayvaz S, Logoglu E. Synthesis and evaluation of a series of aminocyanopyridines as antimicrobial agents. Med Chem Res 2011;1:1-8.
29. Abell AD, Nabbs BK, Battersby AR. The reaction of N -magnesium derivatives of pyrroles with N -mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes. J Org Chem 1998;63:8163-8169.
30. Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147-154.
31. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221-4229.
32. Lineweaver H, Burk DJ. The determination of enzyme dissociation constants. Am Chem Soc 1934;56:658-666.
33. Bradford M. A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of proteindye- binding. Anal Biochem 1976;72:248.
34. Laemmli DK. Clevage of structual proteins during in assembly of the head of bacteriophage T. Nature 1970;227:680-683.
35. Elgemeie CEH, Regaila HA, Shehata N. Novel syhthesis of condensed 4-(2-thienyl)-and 4-(2-furyl)3-cyano-pyridi-2-(1H)- 1-8 7 ones and their conversions into the correponding pyridin-2- (1H)- thione derivatives.Sulfur Lett 1989;9:253-264.
36. D'Ambrosio K, Vitale RM, Dogné JM, Masereel B, Innocenti A, Scozzafava A et al. Carbonic anhydrase inhibitors: bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII. J Med Chem 2008;51:3230-3237.
37. Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK et al. Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry 2008;47:3174-3184.
38. Innocenti A, Maresca A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: thioxolone versus sulfonamides for obtaining isozymeselective inhibitors? Bioorg Med Chem Lett 2008;18:3938-3941.
39. Rigaku /MSC, Inc., 9009 new Trails Drive, The Woodlands, TX 77381.
40. 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;18:1583-1587.
41. Caballero NA, Melendez FJ, Muñoz-Caro C, Niño A. Theoretical prediction of relative and absolute pKa values of aminopyridines. Biophys Chem 2006;124:155-160.
42. Vomasta D, Innocenti A, K?nig B, Supuran CT. Carbonic anhydrase inhibitors: two-prong versus mono-prong inhibitors of isoforms I, II, IX, and XII exemplified by photochromic cis- 1,2-?-dithienylethene derivatives. Bioorg Med Chem Lett 2009;19:1283-1286.