Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: Vidalol B

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 423-428

  Balaydn, Halis T ^a,b   Şentürk, Murat ^c   Göksu, Süleyman ^a   Menzek, Abdullah ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

^b ARTVIN CORUH UNIVERSITY   (Turkey)

^c AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

Author keywords

Bromination; Bromophenols; Carbonic anhydrase; Diphenylmethane; Enzyme inhibition; Glaucoma; Phenol; Vidalol A; Vidalol B

Indexed keywords

1,3 DIBROMO 5 (2,3 DIBROMO 4,5 DIMETHOXYBENZYL) 2,4,6 TRIMETHOXYBENZENE; 2,3 DIBROMO 1 (3 BROMO 2,4,6 TRIMETHOXYBENZYL) 4,5 DIMETHOXYBENZENE; 5,5' (5 BROMO 2,4,6 TRIMETHOXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(3,4 DIBROMO 1,2 DIMETHOXYBENZENE); ACETAZOLAMIDE; BISPHENOL DERIVATIVE; BROMOPHENOL DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE VI; METHOXYPHENOL DERIVATIVE; NATURAL PRODUCT; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; VIDALOL A; VIDALOL B;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; PROTON NUCLEAR MAGNETIC RESONANCE;

BIOLOGICAL AGENTS; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CHEMISTRY TECHNIQUES, SYNTHETIC; ESTERASES; HUMANS; ISOENZYMES; PHENOLS; PHENYLACETATES;

EID: 84864403423     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.05.025     Document Type: Article

References (39)

1. G.W. Gribble The diversity of naturally occurring organobromine compounds Chem. Soc. Rev. 28 1999 335 346
2. H.S. Lee, T.H. Lee, J.H. Lee, C.S. Chae, S.C. Chung, D.S. Shin, J. Shin, and K.B. Oho Inhibition of the pathogenicity of Magnaporthe grisea by bromophenols, isocitrate lyase inhibitors, from the red alga Odonthalia corymbifera J. Agric. Food Chem. 55 2007 6923 6928 (Pubitemid 47338927)
3. K.B. Oh, J.L. Lee, S.C. Chung, J. Shin, H.J. Shin, H.K. Kim, and H.S. Lee Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives Bioorg. Med. Chem. Lett. 18 2008 104 108
4. N. Xu, X. Fan, X. Yan, X. Li, R. Niu, and C.K. Tseng Antibacterial bromophenols from the marine red alga Rhodomela confervoides Phytochemistry 62 2003 1221 1224 (Pubitemid 36383590)
5. W. Wang, Y. Okada, H. Shi, Y. Wang, and T. Okuyama Structures and aldose reductase inhibitory effects of bromophenols from the red alga symphyocladia latiuscula J. Nat. Prod. 68 2005 620 622 (Pubitemid 40586334)
6. H.T. Balaydn, M. Senturk, and A. Menzek Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives Bioorg. Med. Chem. Lett. 22 2012 1352 1357
7. H.T. Balaydin, H. Soyut, D. Ekinci, S. Goksu, S. Beydemir, A. Menzek, and E. Sahin Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products J. Enzym. Inhib. Med. Chem. 27 2012 43 50
8. H.T. Balaydin, I. Gulcin, A. Menzek, S. Goksu, and E. Sahin Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product J. Enzym. Inhib. Med. Chem. 25 2010 685 695
9. X.J. Duan, X.M. Li, and B.G. Wang Highly brominated mono- and bis-phenols from the marine red alga symphyocladia latiuscula with radical-scavenging activity J. Nat. Prod. 70 2007 1210 1213
10. M. Senturk, I. Gulcin, S. Beydemir, O.I. Kufrevioglu, and C.T. Supuran In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds Chem. Biol. Drug Des. 77 2011 494 499
11. M. Senturk, D. Ekinci, S. Goksu, and C.T. Supuran Effects of dopaminergic compounds on carbonic anhydrase isozymes I, II, and VI J. Enzym. Inhib. Med. Chem. 27 2012 365 369
12. Y. Akbaba, H.T. Balaydin, S. Goksu, E. Sahin, and A. Menzek Total synthesis of the biologically active, naturally occurring 3,4-dibromo-5-[2- bromo-3,4-dihydroxy-6-(methoxymethyl) benzyl]benzene-1,2-diol and regioselective o-demethylation of aryl methyl ethers Helv. Chim. Acta 93 2010 1127 1135
13. H.T. Balaydin, Y. Akbaba, A. Menzek, E. Sahin, and S. Goksu First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols Arkivoc XIV 2009 75 87
14. D.F. Wiemer, D.D. Idler, and W. Fenical Vidalols A and B, new anti-inflammatory bromophenols from the Caribbean marine red alga Vidalia obtusaloba Experientia 47 1991 851 853
15. 2 elimination Annu. Rev. Physiol. 50 1988 695 717 (Pubitemid 18088130)
16. C.T. Supuran Carbonic anhydrases: novel therapeutic applications for inhibitors and activators Nat. Rev. Drug Discov. 7 2008 168 181 (Pubitemid 351194064)
17. M. Hilvo, L. Baranauskiene, A.M. Salzano, A. Scaloni, D. Matulis, A. Innocenti, A. Scozzafava, S.M. Monti, A. Di Fiore, G. De Simone, M. Lindfors, J. Jänis, J. Valjakka, S. Pastoreková, J. Pastorek, M.S. Kulomaa, H.R. Nordlund, C.T. Supuran, and S. Parkkila Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes J. Biol. Chem. 283 2008 27799 27809
18. J. Kivela, S. Parkkila, A. Waheed, A.K. Parkkila, W.S. Sly, and H. Rajaniemi Secretory carbonic anhydrase isoenzyme (CA VI) in human serum Clin. Chem. 43 1997 2318 2322 (Pubitemid 28022967)
19. C.T. Supuran, and A. Scozzafava Applications of carbonic anhydrase inhibitors and activators in therapy Expert Opin. Ther. Pat. 12 2002 217 242 (Pubitemid 34145125)
20. D. Ekinci, M. Senturk, and O.I. Kufrevioglu Salicylic acid derivatives: synthesis, features and usage as therapeutic tools Expert Opin. Ther. Pat. 21 2011 1831 1841
21. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran Carbonic anhydrases: current state of the art, therapeutic applications and future prospects J. Enzym. Inhib. Med. Chem. 19 2004 199 229 (Pubitemid 39004275)
22. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors. Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV) Bioorg. Med. Chem. Lett. 18 2008 1583 1587 (Pubitemid 351320621)
23. M. Harig, B. Neumann, H.G. Stammler, and D. Kuck 2,3,6,7,10,11- Hexamethoxytribenzo triquinacene: synthesis, solid-state structure and functionalization of a rigid analogue of cyclotriveratrylene Eur. J. Org. Chem. 11 2004 2381 2397
24. E. Sahin, H.T. Balaydin, S. Goksu, and A. Menzek 2,3-Dibromo-1-[4-(2,3- dibromo-4,5-di-meth-oxy-benz-yl)-2,5-dimeth-oxy-benz-yl]-4,5-dimeth-oxy-benzene Acta Cryst. E66 2010 o3029
25. Y. Cetinkaya, A. Menzek, E. Sahin, and H.T. Balaydn Selective O-demethylation during bromination of (3,4-dimethoxyphenyl)(2,3,4- trimethoxyphenyl)methanone Tetrahedron 67 2011 3483 3489
26. D. Ekinci, S.B. Ceyhun, M. Senturk, D. Erdem, O.I. Kufrevioglu, and C.T. Supuran Characterization and anions inhibition studies of an α-carbonic anhydrase from the teleost fish Dicentrarchus labrax Bioorg. Med. Chem. 19 2011 744 748
27. H. Lineweaver, and D. Burk The determination of enzyme dissocation constants J. Am. Chem. Soc. 56 1934 658 666
28. J.A. Verpoorte, S. Mehta, and J.T. Edsall Esterase activities of human carbonic anhydrases B and C J. Biol. Chem. 242 1967 4221 4229
29. H.T. Balaydin, S. Durdagi, D. Ekinci, M. Senturk, S. Goksu, and A. Menzek Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds J. Enzym. Inhib. Med. Chem. 2011 10.3109/14756366.2011.596836
30. S. Durdagi, M. Senturk, D. Ekinci, H.T. Balaydin, S. Goksu, O.I. Kufrevioglu, A. Innocenti, A. Scozzafava, and C.T. Supuran Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site Bioorg. Med. Chem. 19 2011 1381 1389
31. S.K. Nair, P.A. Ludwig, and D.W. Christianson Two-site binding of phenol in the active site of human carbonic anhydrase II: structural implications for substrate association J. Am. Chem. Soc. 116 1994 3659 3660
32. S. Parkkila, K. Kaunisto, L. Rajaniemi, T. Kumpulainen, K. Jokinen, and H. Rajaniemi Immunohistochemical localization of carbonic anhydrase isoenzymes VI, II and I in human parotid and submandibular glands J. Histochem. Cytochem. 38 1990 941 947 (Pubitemid 20186198)
33. C. Alp, D. Ekinci, M.S. Gultekin, M. Senturk, E. Sahin, and O.I. Kufrevioglu A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies Bioorg. Med. Chem. 18 2010 4468 4477
34. S.B. Ceyhun, M. Senturk, E. Yerlikaya, O. Erdogan, O.I. Kufrevioglu, and D. Ekinci Purification and characterization of carbonic anhydrase from the teleost fish Dicentrarchus labrax (European seabass) liver and toxicological effects of metals on enzyme activity Environ. Toxicol. Pharmacol. 32 2011 69 74
35. D. Ekinci, H. Cavdar, S. Durdagi, O. Talaz, M. Senturk, and C.T. Supuran Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2- b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI Eur. J. Med. Chem. 49 2012 68 73
36. 50) of an enzymatic reaction Biochem. Pharmacol. 22 1973 3099 3108
37. D. Neri, and C.T. Supuran Interfering with pH regulation in tumours as a therapeutic strategy Nat. Rev. Drug Discov. 10 2011 767 777
38. A.A. Barrese, C. Genis, S.Z. Fisher, J.N. Orwenyo, M.T. Kumara, S.K. Dutta, E. Phillips, J.J. Kiddle, C. Tu, D.N. Silverman, L. Govindasamy, M. Agbandje-McKenna, R. McKenna, and B. Tripp Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study Biochemistry 47 2008 3174 3184 (Pubitemid 351364910)
39. A.-M. Chevolot-Magueur, A. Cave, P. Potier, J. Teste, A. Chiaroni, and C. Riche Bromo compounds from Rytiphlea tinctoria (Rhodophyceae) Phytochemistry 15 1976 767 771