4-Toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents

European Journal of Pharmaceutical Sciences - Tập 11 - Trang 325-332 - 2000
Antonio Mastrolorenzo1, Andrea Scozzafava2, Claudiu T. Supuran2
1Università degli Studi, Dipartimento di Scienze Dermatologiche, Centro MTS, Via degli Alfani 37, 50122 Firenze, Italy
2Università degli Studi, Laboratorio di Chimica Inorganica e Bioinorganica, Via Gino Capponi 7, I-50121, Florence, Italy

Tài liệu tham khảo

Branda, 1988, Cellular pharmacology of chloroquinoxaline sulfonamide and a related compound in murine B16 melanoma cells, Biochem. Pharmacol., 37, 4557, 10.1016/0006-2952(88)90672-7 Briganti, 1999, Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties, Bioorg. Med. Chem. Lett., 9, 2043, 10.1016/S0960-894X(99)00310-8 Chern, 1997, Synthesis and cytotoxic evaluation of substituted sulfonyl-N-hydroxyguanidine derivatives as potential antitumor agents, J. Med. Chem., 40, 2276, 10.1021/jm9607818 Ehlhardt, 1991, Metabolism and disposition of the anticancer agent sulofenur in rat, mouse, monkey and human, Drug Metab. Dispos., 19, 370 Fields, 1990, Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids, Int. J. Protein Res., 35, 161, 10.1111/j.1399-3011.1990.tb00939.x Flygare, J., Medina, J.C., Shan, B., Clark, D.L., Rosen, T., 1998. Pentafluorobenzenesulfonamides and analogs. WO 98/05315. Houghton, 1996, Antitumor diarylsulfonylureas: novel agents with unfulfilled promise, Invest. New Drugs, 14, 271, 10.1007/BF00194530 Howbert, 1990, Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure–activity relationships, J. Med. Chem., 33, 2393, 10.1021/jm00171a013 Medina, 1999, Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells, Bioorg. Med. Chem. Lett., 9, 1843, 10.1016/S0960-894X(99)00276-0 Medina, 1998, Novel antineoplastic agents with efficacy against multidrug resistant tumor cells, Bioorg. Med. Chem. Lett., 8, 2653, 10.1016/S0960-894X(98)00477-6 Mohamadi, 1992, Sulfonylureas: a new class of cancer chemotherapeutic agents, J. Med. Chem., 35, 3012, 10.1021/jm00094a013 Owa, 1999, Discovery of novel antitumor sulfonamides targeting G1 phase of the cell cycle, J. Med. Chem., 42, 3789, 10.1021/jm9902638 Rigas, 1995, Clinical and pharmacology study of chloroquinoxaline sulfonamide given on a weekly schedule, Cancer Chemother. Pharmacol., 35, 483, 10.1007/BF00686832 Rush, 1992, Effects of diarylsulfonylurea antitumor agents on the function of mitochondria isolated from rat liver and GC3/c1 cells, Biochem. Pharmacol., 44, 2387, 10.1016/0006-2952(92)90684-B Scozzafava, 1999, Carbonic anhydrase inhibitors. Part 74. Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring?, J. Med. Chem., 42, 2641, 10.1021/jm9900523 Scozzafava, 1999, Carbonic anhydrase inhibitors: synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route, J. Med. Chem., 42, 3690, 10.1021/jm9901879 Scozzafava, 1999, Carbonic anhydrase inhibitors. Part 66. Arylsulfonylureido and arylureido-substituted aromatic and heterocyclic sulfonamides: towards selective inhibitors of carbonic anhydrase isozyme I, J. Enzyme Inhib., 14, 343, 10.3109/14756369909030328 Scozzafava, 2000, Carbonic anhydrase inhibitors: synthesis of N-morpholyl-thiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV, Bioorg. Med. Chem. Lett., 10, 1117, 10.1016/S0960-894X(00)00178-5 Scozzafava, 2000, Carbonic anhydrase activators. Part 24. High affinity isozymes I, II and IV activators, derivatives of 4-(4-chlorophenylsulfonylureido-amino acyl)ethyl-1H-imidazole, Eur. J. Pharm. Sci., 10, 29, 10.1016/S0928-0987(99)00086-X Scozzafava, 2000, Protease inhibitors: synthesis of potent matrix metalloproteinase and bacterial collagenase inhibitors incorporating N-4-nitrobenzylsulfonyl glycine hydroxamate moieties, J. Med. Chem., 42, 1858, 10.1021/jm990594k Sirotnak, 2000, Markedly decreased binding of vincristine to tubulin in vinca alkaloid-resistant Chinese hamster cells is associated with selective overexpression of alpha and beta tubulin isoforms, Biochem. Biophys. Res. Commun., 269, 21, 10.1006/bbrc.2000.2246 Sosinski, 1994, Cross-resistance to antitumor diarylsulfonylureas and collateral sensitivity to mitochondrial toxins in a human cell line selected for resistance to the antitumor agent N-(5-indanylsulfonyl)-N′-(4-chlorophenyl)urea, Mol. Pharmacol., 45, 962 Supuran, C.T., Briganti, F., Tilli, S., Chegwidden, R., Scozzafava, A., 2000. Carbonic anhydrase inhibitors: sulfonamides as antitumor drugs? J. Med. Chem. (in press). Supuran, 2000, Carbonic anhydrase inhibitors and their therapeutic potential, Exp. Opin. Ther. Patents, 10, 575, 10.1517/13543776.10.5.575 1997, 7 Toth, 1997, Sulfonimideamide analogs of oncolytic sulfonylureas, J. Med. Chem., 40, 1018, 10.1021/jm960673l Ulrich, 1965, The chemistry of sulfonyl isocyanates, Chem. Rev., 65, 369, 10.1021/cr60235a002 Yoshino, 1992, Novel sulfonamides as potential systemically active antitumor agents, J. Med. Chem., 35, 2496, 10.1021/jm00091a018