Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

European Journal of Medicinal Chemistry

Volumn 66, Issue , 2013, Pages 1-11

  Wang, Zhong Chang ^a   Qin, Ya Juan ^a   Wang, Peng Fei ^a   Yang, Yong An ^a   Wen, Qing ^a   Zhang, Xin ^a   Qiu, Han Yue ^a   Duan, Yong Tao ^a   Wang, Yan Ting ^a   Sang, Ya Li ^a   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

3D QSAR; Antitumor activity; Carbonic anhydrase; CCK 8 assay; Sulfonamide derivatives

Indexed keywords

4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZENESULFONAMIDE; 4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4 METHYLPYRI MIDIN 2 YL) BENZESULFONAMIDE; 4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4, 6 DIMETHYL PYRIMIDIN 2 YL) BENZENESULFONAMIDE; 4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (5 METHYLISOXAZOL 3 YL) BENZESULFONAMIDE; 4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (THIAZOL 2 YL) BENZENESULFONAMIDE; 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZENE SULFONAMIDE; 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4 METHYLPYRIMIDIN 2 YL) BENZENESULFONAMIDE; 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4,6 DIMETHYLPYRIMIDIN 2 YL) BENZENESULFONAMIDE; 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (5 METHYLISOXAZOL 3 YL) BENZENESULFONAMIDE; 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (THIAZOL 2 YL) BENZENESULFONAMIDE; 4 ((6, 8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZENESULFONAMIDE; 4 ((6, 8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (THIAZOLE 2 YL) BENZENESULFONAMIDE; 4 ((6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4 METHYLPYRIMIDIN 2 YL) BENZENESULFONAMIDE; 4 ((6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (4, 6 DIMETHYLPYRIMIDIN 2 YL)BENZESULFONAMIDE; 4 ((6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) N (5 METHYLISOXAZOL 3 YL) BENZENESULFONAMIDE; 4 CHLORO 2 OXO 2H CHROMENE 3 CARBALDEHYDE; 4 CHLORO 6 METHYL 2 OXO 2H CHROMENE 3 CARBALDEHYDE; 8 DITERTBUTYL 4 CHLORO 2 OXO 2H CHROMENE 3 CARBALDEHYDE; ANTINEOPLASTIC AGENT; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; COUMARIN DERIVATIVE; DOXORUBICIN; ISOENZYME; N CARBAMIMIDOYL 4 ((4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZENESULFONAMIDE; N CARBAMIMIDOYL 4 ((4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZENESULFONAMIDE; N CARBAMIMIDOYL 4 ((6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL) METHYLENEAMINO) BENZESULFONAMIDE; SEMAXANIB; SULFONAMIDE; UNCLASSIFIED DRUG; 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4 METHYLPYRI MIDIN 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4,6 DIMETHYL PYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (THIAZOL 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO]BENZENESULFONAMIDE; 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4 METHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4,6 DIMETHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (THIAZOL 2 YL)BENZENESULFONAMIDE; 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO]BENZENE SULFONAMIDE; 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4 METHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (4,6 DIMETHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO] N (THIAZOL 2 YL)BENZENESULFONAMIDE; 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO]BENZENESULFONAMIDE; 6,8 DITERTBUTYL 4 CHLORO 2 OXO 2H CHROMENR 3 CARBALDEHYDE; N CARBAMIMIDOYL 4 [(4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO]BENZENESULFONAMIDE; N CARBAMIMIDOYL 4 [(4 CHLORO 6 METHYL 2 OXO 2H CHROMEN 3 YL)METHYLENE AMINO]BENZENESULFONAMIDE; N CARBAMIMIDOYL 4 [(6,8 DI TERT BUTYL 4 CHLORO 2 OXO 2H CHROMEN 3 YL)METHYLENEAMINO]BENZENESULFONAMIDE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; MACROPHAGE; MOUSE; NONHUMAN; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; BINDING AFFINITY; BREAST CANCER; DRUG CONFORMATION; HYDROPHOBICITY; IN VITRO STUDY; MOLECULAR DOCKING;

EID: 84879055244     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.035     Document Type: Article

References (42)

1. A. Cincinelli, T. Martellini, A. Innocenti, A. Scozzafava, C.T. Supuran, Purification and inhibition studies with anions and sulfonamides of an α-carbonic anhydrase from the Antarctic seal Leptonychotes weddellii, Bioorg. Med. Chem. 19 (2011) 1847-1851.
2. B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran, S.A. Poulsen, Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked o-glycosides of benzene sulfonamides, J. Med. Chem. 50 (2007) 1651-1657. (Pubitemid 46564385)
3. M. Lopez, L.F. Bornaghi, A. Innocenti, D. Vullo, S.A. Charman, C.T. Supuran, S.A. Poulsen, Sulfonamide linked neoglycoconjugates-a new class of inhibitors for cancer-associated carbonic anhydrases, J. Med. Chem. 53 (2010) 2913-2926.
4. 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. Janis, J. Valjakka, S. Pastorekova, J. Pastorek, M.S. Kulomaa, H.R. Nordlund, C.T. Supuran, S. Parkkila, Biochemical characterization of CA IX: one of the most active carbonic anhydrase isozymes, J. Biol. Chem. 283 (2008) 27799-27809.
5. J. Chiche, K. Ilc, J. Laferriere, E. Trottier, F. Dayan, N.M. Mazure, M.C. Brahimi-Horn, J. Pouysségur, Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH, Cancer Res. 69 (2009) 358-368.
6. M.C. Brahimi-Horn, G. Bellot, J. Pouysségur, Hypoxia and energetic tumour metabolism, Curr. Opin. Genet. Dev. 21 (2011) 67-72.
7. J.C. Morris, J. Chiche, C. Grellier, M. Lopez, L.F. Bornaghi, A. Maresca, C.T. Supuran, Jacques. Pouysségur, S.A. Poulsen, J. Med. Chem. 54 (2011) 6905-6918.
8. P. Swietach, R. Vaughan-Jones, A. Harris, Regulation of tumor pH and the role of carbonic anhydrase 9, Cancer Metastasis Rev. 26 (2007) 299-310. (Pubitemid 47101667)
9. E. Svastova, A. Hulikova, M. Rafajova, M. Zatovicova, A. Gibaduli-nova, A. Casini, A. Cecchi, A. Scozzafava, C.T. Supuran, J. Pastorek, S. Pastorekova, Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH, FEBS Lett. 577 (2004) 439-445. (Pubitemid 39535327)
10. F. Pacchiano, F. Carta, P.C. McDonald, Y.M. Lou, D. Vullo, A. Scozzafava, S. Dedhar, C.T. Supuran, Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show inhibitory activity in a model of breast cancer metastasis, J. Med. Chem. 54 (2011) 1896-1902.
11. C.T. Supuran, F. Briganti, S. Tilli, W.R. Chegwidden, A. Scozzafava, Carbonic anhydrase inhibitors: sulfonamides as antitumor agents, Bioorg. Med. Chem. 9 (2001) 703-714. (Pubitemid 32208589)
12. (a) C.C. Wykoff, N.J. Beasley, P.H. Watson, K.J. Pastorek, J. Turner, A. Sibtain, G.D. Wilson, H. Turley, K.L. Talks, P.H. Maxwell, C.W. Pugh, P.J. Ratcliffe, A.L. Harris, Hypoxia-inducible regulation of tumor-associated carbonic anhydrases, Cancer Res. 60 (2000) 7075-7083;
13. (b) C.P.S. Potter, A.L. Harris, Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer, Br. J. Cancer 89 (2003) 2-7;
14. (c) R.K. Jain, Normalization of tumor vasculature: an emerging concept in antiangiogenic therapy, Science 307 (2005) 58-62.
15. W.A. Denny, Tumor-activated prodrugs. A new approach to cancer therapy, Cancer Invest. 22 (2004) 604-619. (Pubitemid 39506881)
16. J. Chiche, M. Brahimi-Horn, J. Pouysségur, Tumour hypoxia induces a metabolic shift causing acidosis: a common feature in cancer, J. Cell. Mol. Med. 14 (2010) 771-794.
17. Y. Yoshino, N. Ueda, J. Niijima, H. Sugumi, Y. Kotake, N. Koyanagi, K. Yoshimatsu, M. Asada, T. Watanabe, T. Nagasu, K. Tsukahara, A. Iijima, K.J. Kitoh, Med. Chem. 35 (1992) 2496-2497.
18. A. Casini, A. Scozzafava, A. Mastrolorenzo, C.T. Supuran, Sulfonamides and sulfonylated derivatives as anticancer agents, Curr. Cancer Drug Targets 2 (2002) 55-75. (Pubitemid 34627379)
19. B. Shan, J.C. Medina, E. Santha, W.P. Frankmoelle, T.C. Chou, R.M. Learned, M.R. Narbut, D. Stott, P. Wu, J.C. Jaen, T. Rosen, P.B.M.W.M. Timmermans, H. Beckmann, Proc. Selective, covalent modification of β-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors, Natl. Acad. Sci. U. S. A. 96 (1999) 5686-5691. (Pubitemid 29234679)
20. H. Tanaka, N. Ohshima, M. Ikenoya, K. Komori, F. Katoh, H. Hidaka, HMN-176, an active metabolite of the synthetic antitumor agent HMN-214, restores chemosensitivity to multidrug-resistant cells by targeting the transcription factor NF-Y, Cancer Res. 63 (2003) 6942-6947. (Pubitemid 37322980)
21. C.T. Supuran, A. Scozzafava, Carbonic anhydrase inhibitors and their therapeutic potential, Exp. Opin. Ther. Patents 10 (2000) 575-600.
22. J. Drew, Drug discovery: a historical perspective, Science 287 (2000) 1960-1964.
23. R. Bashir, S. Ovais, S. Yaseen, H. Hamid, M.S. Alam, M. Samim, S. Singh, K. Javed, Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents, Bioorg. Med. Chem. 21 (2011) 4301-4305.
24. A. Maresca, C. Temperini, L. Pochet, B. Masereel, A. Scozzafava, C.T. Supuran, Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins, J. Med. Chem. 53 (2010) 335-344.
25. C.T. Supuran, A. Scozzafava, A. Casini, Med. Res. Rev. 23 (2003) 146-189.
26. A. Thiry, M. Ledecq, A. Cecchi, J.M. Dogne, J. Wouters, C.T. Supuran, B.J. Masereel, Med. Chem. 49 (2006) 2743-2749.
27. W.T. Gao, W.R. Hou, M.R. Zheng, Chin. J. Org. Chem. 28 (2008) 2011-2015.
28. R.G. Khalifah, The carbon dioxide hydration activity of carbonic anhydrase I. Stop-flow kinetic studies on the native human isoenzymes B and C, J. Biol. Chem. 246 (1971) 2561-2573.
29. (a) C.T. Supuran, Carbonic anhydrases: novel therapeutic applications for inhibitors and activators, Nat. Rev. Drug Discov. 7 (2008) 168-181;
30. (b) O. Ozensoy, G. De Simone, C.T. Supuran, Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII, Curr. Med. Chem. 17 (2010) 1516-1526;
31. (c) G. De Simone, C.T. Supuran, Carbonic anhydrase IX: biochemical and crystallographic characterization of a novel antitumor target, Biochim. Biophys. Acta 1804 (2010) 404-409;
32. (d) C.T. Supuran, Carbonic anhydrase inhibitors, Bioorg. Med. Chem. Lett. 20 (2010) 3467-3474.
33. F. Pacchiano, M. Aggarwal, B.S. Avvaru, A.H. Robbins, A. Scozzafava, R. McKenna, C.T. Supuran, Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido- benzenesulfonamides and correlate to inhibitor potency, Chem. Commun. (Cambridge, U. K.) 46 (2010) 8371-8373.
34. L.T. Webster, A. Gilman, T.W. Rall, A.S. Nies, P. Taylor, Drugs used in the chemotherapy of protozoal infections, in: The Pharmacological Basis of the Rapeutics, eighth ed., Pergamon Press, New York, 1990, pp. 999-1007.
35. W.J. Egan, K.J. Merz, J.J. Baldwin, Prediction of drug absorption using multivariate statistics, J. Med. Chem. 43 (2000) 3867-3877.
36. L. Dawara, R.V. Singh, Synthesis, spectroscopic characterization, antimicrobial, pesticidal and nematicidal activity of some nitrogen-oxygen and nitrogen-sulfur donor coumarins based ligands and their organotin(IV) complexes, Appl. Organomet. Chem. 25 (2011) 643-652.
37. A. Kasabe, G.V. Mohite, J. Vidhate, Synthesis, characterization and primary antimicrobial, antifungal activity evaluation of Schiff bases of 4-chloro- (3-substituted-phenylimino)-methyl-[2H]-chromene-2-one, E-Journal Chem. 7 (2010) 377-382.
38. R.G. Khalifah, The carbon dioxide hydration activity of carbonic anhydrase, J. Biol. Chem. 246 (1971) 2561-2573.
39. (a) J.Y. Winum, D. Vullo, A. Casini, J. L.nMontero, A. Scozzafava, C.T. Supuran, Carbonic anhydrase inhibitors: inhibition of trans-membrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates, J. Med. Chem. 46 (2003) 5471-5477;
40. (b) A. Cecchi, A. Hulikova, J. Pastorek, S. Pastorekova, A. Scozzafava, J.Y. Winum, J.L. Montero, C.T. Supuran, Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis, J. Med. Chem. 48 (2005) 4834-4841;
41. (c) B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran, S.A. Poulsen, Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked o-glycosides of benzene sulfonamides, J. Med. Chem. 50 (2007) 1651-1657.
42. G.L. Bras, C. Radanyi, J.F. Peyrat, J.D. Brion, M. Alami, V. Marsaud, B. Stella, J.M. Renoir, New novobiocin analogues as antitumor agents in breast cancer cells and potential inhibitors of heat shock protein 90, J. Med. Chem. 50 (2007) 6189-6200.