Quaternary ammonium substituted thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 6, 2006, Pages 2052-2059

  May, Jesse A ^a   Namil, Abdelmoula ^a   Chen, Hwang Hsing ^a   Dantanarayana, Anura P ^a   Dupré, Brian ^a   Liao, John C ^a  

^a ALCON RESEARCH LTD   (United States)

Author keywords

Carbonic anhydrase; Enzyme inhibitor; Membrane bound; Quaternary ammonium; Sulfonamide

Indexed keywords

2 (3 CHLOROPROPYL) 3 (4 MORPHOLINOMETHYL) 2H THIENO[3,2 E] 1,2 THIAZINE 6 SULFONAMIDE 1,1 DIOXIDE HYDROCHLORIDE; 2 (AMINOSULFONYL) 7,8 DIHYDRO SPIRO[MORPHOLINE 4,6'(5H) PYRAZINO[1,2 B]THIENO[3,2 E] 1,2 THIAZINIUM] 10,10 DIOXIDE CHLORIDE; 2 (AMINOSULFONYL) 8,9 DIHYDRO SPIRO[MORPHOLINE 4,6'(7H) 5H THIENO[3',2':5,6][1,2]THIAZINE[2,3 A][1,4]DIAZEPINIUM] 11,11 DIOXIDE CHLORIDE; 4 [[6 (AMINOSULFONYL) 2 (2 METHOXYETHYL) 1,1 DIOXO 2H THIENO[3,2 E] 1,2 THIAZIN 3 YL]METHYL] 4 METHYL MORPHOLINIUM CHLORIDE; 6 (AMINOSULFONYL) N,N,N, 2 TETRAMETHYL 1,1, DIOXO 2H THIENO[3,2 E] 1,2 THIAZINE 3 METHANAMINIUM CHLORIDE; 6 (AMINOSULFONYL) N,N,N, TRIMETHYL 1 (3 METHOXY PHENYL) 1,1 DIOXO 2H THIENO[3,2 E] 1,2 THIAZINE 3 METHANAMINIUM CHLORIDE; 6 (AMINOSULFONYL) N,N,N, TRIMETHYL 1,1, DIOXO 2H THIENO[3,2 E] 1,2 THIAZINE 2 PROPANAMINIUM CHLORIDE; 6 (AMINOSULFONYL) N,N,N, TRIMETHYL 2 (3 METHOXY PHENYLMETHYL) 1,1 DIOXO 2H THIENO[3,2 E] 1,2 THIAZINE 3 METHANAMINIUM CHLORIDE; BRINZOLAMIDE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; MAFENIDE; QUATERNARY AMMONIUM DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CELL TRANSPORT; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; HUMAN; IC 50; IN VITRO STUDY; MEMBRANE PERMEABILITY;

CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASE IV; CELL MEMBRANE; CELLS, CULTURED; HUMANS; MOLECULAR STRUCTURE; OXIDES; QUATERNARY AMMONIUM COMPOUNDS; SULFONAMIDES; THIAZINES;

HUMAN ECHOVIRUS 1;

EID: 32044461279     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.10.054     Document Type: Article

References (28)

1. K. Mori, Y. Ogawa, K. Ebihara, N. Tamura, K. Tashiro, T. Kuwahara, M. Mukoyama, A. Sugawara, S. Ozaki, I. Tanaka, and K. Nakao J. Biol. Chem. 274 1999 15701 15705
2. O. Tureci, U. Sahin, E. Vollmar, S. Siemer, E. Gottert, G. Seitz, A.K. Parkkila, G.N. Shah, J.H. Grubb, M.. Pfreundschuh, and W.S. Sly Proc. Natl. Acad. Sci. U.S.A. 95 1998 7608 7613
3. Y. Ridderstrale, P.J. Wistrand, and W.F. Brechue Invest. Ophthalmol. Vis. Sci. 35 1994 2577 2584
4. T.H. Maren J. Glaucoma 1995 4
5. R.P. Henry, Y. Wang, and C.M. Wood Am. J. Physiol. 272 1997 R1754 R1761
6. S.Y. Liao, S. Ivanov, A. Ivanova, S. Ghosh, M.A. Cote, K. Keefe, M. Coca-Prados, E.J. Stanbridge, and M.I. Lerman J. Med. Genet. 40 2003 257 261
7. N. Robertson, C. Potter, and A.L. Harris Cancer Res. 64 2004 6160 6165
8. C.T. Supuran, F. Briganti, S. Tilli, W.R. Chegwidden, and A. Scozzafava Bioorg. Med. Chem. 9 2001 703 714
9. S. Parkkila, H. Rajaniemi, A.K. Parkkila, J. Kivela, A. Waheed, S. Pastorekova, J. Pastorek, and W.S. Sly Proc. Natl. Acad. Sci. U.S.A. 97 2000 2220 2224
10. D.A. Whittington, J.H. Grubb, A. Waheed, G.N. Shah, W.S. Sly, and D.W. Christianson J. Biol. Chem. 279 2004 7223 7228
11. S. Parkkila, A.K. Parkkila, H. Rajaniemi, G.N. Shah, J.H. Grubb, A. Waheed, and W.S. Sly Proc. Natl. Acad. Sci. U.S.A. 98 2001 1918 1923
12. J.P. Tinker, R. Coulson, and I.M. Weiner J. Pharmacol. Exp. Ther. 218 1981 600 607
13. T.H. Maren, C.W. Conroy, G.C. Wynns, and D.R. Godman J. Pharmacol. Exp. Ther. 280 1997 98 104
14. T.A. Heming, C. Geers, G. Gros, A. Bidani, and E.D. Crandall J. Appl. Physiol. 61 1986 1849 1856
15. R.P. Henry Am. J. Physiol. 252 1987 R959 R965
16. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337 2347
17. C.T. Supuran, A. Scozzafava, M.A. Ilies, B. Iorga, T. Cristea, F. Briganti, F. Chiraleu, and M.D. Banciu Eur. J. Med. Chem. 33 1998 577 594
18. T.H. Maren Physiol. Rev. 47 1967 595 781
19. T.H. Maren Mol. Pharmacol. 41 1992 419 426
20. C.T. Supuran, and A. Scozzafava J. Enzyme Inhib. Med. Chem. 19 2004 269 273
21. J.A. Gottfried, and M. Chesler J. Neurophysiol. 74 1995 2774 2777
22. A.L. Banerjee, M. Swanson, B.C. Roy, X. Jia, M.K. Haldar, S. Mallik, and D.K. Srivastava J. Am. Chem. Soc. 126 2004 10875 10883
23. C.Y. Kim, D.A. Whittington, J.S. Chang, J. Liao, J.A. May, and D.W. Christianson J. Med. Chem. 45 2002 888 893
24. H.H. Chen, S. Gross, J. Liao, M. McLaughlin, T. Dean, W.S. Sly, and J.A. May Bioorg. Med. Chem. 8 2000 957 975
25. R.E. Conrow, W.D. Dean, P.W. Zinke, M.E. Deason, S.J. Sproull, A.P. Dantanarayana, and M.T. DuPriest Org. Process Res. Dev. 3 1999 114 120
26. E.A. Newman Glia 11 1994 291 299
27. S.B. Ross, R. Sandberg, B.A. Akerman, K.E. Domeij, G. Stening, and S. Svensson J. Med. Chem. 16 1973 787 790
28. S.B. Ross J. Pharm. Pharmacol. 27 1975 322 328