Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue 4, 2016, Pages 568-573

  Gul, Halise Inci ^a   Kucukoglu, Kaan ^a   Yamali, Cem ^a   Bilginer, Sinan ^a   Yuca, Hafize ^a   Ozturk, Iknur ^a   Taslimi, Parham ^a   Gulcin, Ilhami ^a,b   Supuran, Claudiu T ^c  

^a ATATÜRK UNIVERSITY   (Turkey)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

2 Acethylfuran; 2 acethylthiophene; acetophenones; carbonic anhydrase; enzyme inhibition; indanone; sulfonamide

Indexed keywords

4 [2 (2,3 DIHYDRO 1H INDEN 1 YLIDENE)HYDRAZINO]BENZENESULFONAMIDE; 4 [2 (2,3 DIHYDRO 2H INDEN 2 YLIDENE)HYDRAZINO]BENZENESULFONAMIDE; 4 [2 [1 (FURAN 2 YL)ETHYLIDENE]HYDRAZINO]BENZENESULFONAMIDE; ACETOPHENONE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE; KETONE DERIVATIVE; UNCLASSIFIED DRUG; BENZENESULFONAMIDE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; SULFONAMIDE;

AFFINITY CHROMATOGRAPHY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; ENZYME INHIBITION; HEATING; MASS SPECTROMETRY; MELTING POINT; MICROWAVE IRRADIATION; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84964621525     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2015.1047359     Document Type: Article

References (58)

1. ArasHisar Ş, Hisar O, Beydemir Ş, et al. Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Acta Vet Hung 2004;52: 413-22.
2. Hisar O, Beydemir Ş, Gülçin İ, et al. Effect of low molecular weight plasma inhibitors of rainbow trout (Oncorhyncytes mykiss) on human erythrocytes carbonic anhydrase-II isozyme activity in vitro and rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2005;20: 35-9.
3. Hisar O, Beydemir Ş, Gülçin İ, et al. The effect of melatonin hormone on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Turk J Vet Anim Sci 2005;29:841-5.
4. Ward C, Langdon SP, Mullen P, et al. New strategies for targeting the hypoxic tumour microenvironment in breast cancer. Cancer Treat Rev 2013;39:171-9.
5. Tanpure RP, Ren B, Peat TS, et al. Carbonic anhydrase inhibitors with dual-tail moieties to match the hydrophobic and hydrophilic halves of the carbonic anhydrase active site. J Med Chem 2015;58: 1494-501.
6. Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767-77.
7. Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. The inhibitory effect of ethanol on carbonic anhydrase isoenzymes: in vivo and in vitro studies. J Enzyme Inhib Med Chem 2008;23:266-70.
8. Boztaş M, Çetinkaya Y, Topal M, et al. Synthesis and carbonic anhydrase isoenzymes I, II, IX, and XII inhibitory effects of dimethoxy-bromophenol derivatives incorporating cyclopropane moieties. J Med Chem 2015;58:640-50.
9. Yildirim A, Atmaca U, Keskin A, et al. N-Acylsulfonamides strongly inhibit human carbonic anhydrase isoenzymes I and II. Bioorg Med Chem 2015;23:2598-605.
10. Alterio V, De Simone G, Monti SM, et al. Carbonic anhydrase inhibitors: inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides-solution and crystallographic studies. Bioorg Med Chem Lett 2007;17:4201-7.
11. Şentürk M, Gülçin İ, Daştan A, et al. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207-11.
12. Arabaci B, Gülçin İ, Alwasel S. Capsaicin: a potent inhibitor of carbonic anhydrase isoenzymes. Molecules 2014;19:10103-14.
13. Güney M, Coşkun A, Topal F, et al. Oxidation of cyanobenzocycloheptatrienes: synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives. Bioorg Med Chem 2014;22:3537-43.
14. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-81.
15. Coban TA, Beydemir S, Gücin İ, et al. Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV. Bioorg Med Chem 2009;17:5791-5.
16. Akbaba Y, Akincioǧlu A, Göçer H, et al. Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins. J Enzyme Inhib Med Chem 2014;29: 35-42.
17. Göksu S, Naderi A, Akbaba Y, et al. Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies. Bioorg Chem 2014;56:75-82.
18. Sethi KK, Verma SM, Tanç M, et al. Carbonic anhydrase inhibitors: synthesis and inhibition of the cytosolic mammalian carbonic anhydrase isoforms I, II and VII with benzene sulfonamides incorporating 4,5,6,7-tetrachlorophthalimide moiety. Bioorg Med Chem 2013;21:5168-74.
19. Öztürk Sarikaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem Biol Drug Des 2010;75:515-20.
20. Topal M, Gülçin İ. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894-902.
21. Innocenti A, Öztürk Sarikaya SB, et al. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159-64.
22. Çetinkaya Y, Göçer H, Gülçin İ, Menzek A. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives. Arch Pharm 2014;347:354-9.
23. Akincioǧlu A, Topal M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68-76.
24. Gülçin İ, Beydemir Ş, Büyükokuroǧlu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613-16.
25. Beydemir Ş, Gülçin İ. Effect of melatonin on carbonic anhydrase from human erythrocyte in vitro and from rat erythrocyte in vivo. J Enzyme Inhib Med Chem 2004;19:193-7.
26. Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo. Biol Pharm Bull 2007;30:2257-61.
27. Aksu K, Nar M, Tanç M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925-31.
28. Atasaver A, Özdemir H, Gülçin İ, Küfrevioǧlu Öİ. One-step purification of lactoperoxidase from bovine milk by affinity chromatography. Food Chem 2013;136:864-70.
29. Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Arch Pharm 2014;347:950-7.
30. Şentürk M, Gülçin İ, Beydemir Ş, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494-9.
31. Öztürk Sarikaya SB, Topal F, Şentürk M, et al. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259-62.
32. Nar M, Çetinkaya Y, Gülçin İ, Menzek A. (3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors. J Enzyme Inhib Med Chem 2013;28:402-6.
33. Laemmli DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680-5.
34. Gülçin İ, Küfrevioǧlu Öİ, Oktay M. Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibition effects of some chemicals on the enzyme activity. J Enzyme Inhib Med Chem 2005;20:297-302.
35. Şişecioǧlu M, Çankaya M, Gülçin İ, Özdemir M. Interactions of melatonin and serotonin to lactoperoxidase enzyme. J Enzyme Inhib Med Chem 2010;25:779-83.
36. Şişecioǧlu M, Gülçin İ, Çankaya M, et al. Purification and characterization of peroxidase from Turkish black radish (Raphanus sativus L.). J Med Plants Res 2010;4:1187-96.
37. Gülçin İ, Beydemir Ş, Çoban TA, Ekinci D. The inhibitory effect of dantrolene sodium and propofol on 6-phosphogluconate dehydrogenase from rat erythrocyte. Fresen Environ Bull 2008;17: 1283-7.
38. Şentürk M, Gülçin İ, Çiftci M, Küfrevioǧlu Öİ. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull 2008;31: 2036-9.
39. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221-9.
40. Akincioǧlu A, Akbaba Y, Göçer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:379-85.
41. Göçer H, Akincioǧlu A, Öztaşkin N, et al. Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds. Arc Pharm 2013;346:783-92.
42. Bradford MM. Rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-54.
43. Köksal E, Gülçin İ. Purification and characterization of peroxidase from cauliflower (Brassica oleracea L.) buds. Protein Peptide Lett 2008;15:320-6.
44. Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658-66.
45. Köksal E, Aǧgül AG, Bursal E, Gülçin İ. Purification and characterization of peroxidase from sweet gourd (Cucurbita Moschata Lam. Poiret). Int J Food Propert 2012;15:1110-19.
46. Bekhit AA, Ashour HMA, Abdel-Rahman HM, et al. Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents. J Enzyme Inhib Med Chem 2009;24: 296-309.
47. Sharma PK, Chandak N, Kumar P, et al. Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents. Eur J Med Chem 2011;46:1425-32.
48. 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.
49. Clare BW, Supuran CT. A perspective on quantitative structure-activity relationships and carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol 2006;2:113-37.
50. Thiry A, Dogne JM, Supuran CT, Masereel B. Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: drug design and mechanism of action. Curr Pharm Des 2008;14:661-71.
51. Mann T, Keilin D. Sulphanilamide as a specific carbonic anhydrase inhibitor. Nature 1940;146:164-5.
52. Supuran CT, Scozzafava A, Casini A. Development of sulfonamide carbonic anhydrase inhibitors (CAIs). In: Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase: its inhibitors and activators. Boca Raton (FL): CRC Press; 2004:67-147.
53. Alterio V, Di Fiore A, D'Ambrosio K, et al. X-ray crystallography of CA inhibitors and its importance in drug design. In: Supuran CT, Winum JY, eds. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Hoboken (NJ): Wiley; 2009: 73-138.
54. Casini A, Abbate F, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a bis-sulfonamide-two heads are better than one? Bioorg Med Chem Lett 2003;13:2759-63.
55. Abbate F, Casini A, Owa T, et al. Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 2004;14:217-23.
56. Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19: 199-229.
57. D'Ascenzio M, Carradori S, De Monte C, et al. Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII. Bioorg Med Chem 2014;22:1821-31.
58. Vullo D, Scozzafava A, Pastorekova S, et al. Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Bioorg Med Chem Lett 2004;14:2351-6.