Sulfonimidamides as Sulfonamides Bioisosteres: Rational Evaluation through Synthetic, in Vitro, and in Vivo Studies with γ-Secretase Inhibitors

ChemMedChem

Volumn 7, Issue 3, 2012, Pages 396-399

  Sehgelmeble, Fernando ^a   Janson, Juliette ^a   Ray, Colin ^a   Rosqvist, Susanne ^a   Gustavsson, Susanne ^a   Nilsson, Linda I ^a   Minidis, Alexander ^a   Holenz, Jörg ^a   Rotticci, Didier ^a   Lundkvist, Johan ^a   Arvidsson, Per I ^a,b,c  

^a ASTRAZENECA R AND D   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Bioisosteres; Drugs; Gamma secretase; Sulfonamides; Sulfonimidamides

Indexed keywords

BEGACESTAT; FUNCTIONAL GROUP; GAMMA SECRETASE INHIBITOR; GSI 136; SULFONAMIDE; SULFONIMIDAMIDE; UNCLASSIFIED DRUG;

ARTICLE; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; PLASMA PROTEIN BINDING; PRIORITY JOURNAL; SOLUBILITY; SYNTHESIS;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; BRAIN; CELLS, CULTURED; FEMALE; HEPATOCYTES; HUMANS; INJECTIONS, SUBCUTANEOUS; MICE; MICE, INBRED C57BL; NEUROPROTECTIVE AGENTS; STEREOISOMERISM; SULFONAMIDES;

EID: 84857730058     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200014     Document Type: Article

References (32)

1. The structural search in Thomson Reuters Integrity for sulfonamides under active development was performed in October 2011.
2. P. Ciapetti, B. Giethen in The Practice of Medicinal Chemistry, 3rded. (Ed.: C.G. Wermuth), Academic Press, London, 2008, p.290.
3. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529.
4. E. S. Levchenko, I. E. Sheinkman, A. V. Kirsanov, Zh. Obshch. Khim. 1960, 30, 1941.
5. E. S. Levchenko, N. Y. Derkach, A. V. Kirsanov, Zh. Obshch. Khim. 1962, 32, 1208.
6. D. Leca, A. Toussaint, C. Mareau, L. Fensterbank, E. Lacôte, M. Malacria, Org. Lett. 2004, 6, 3573.
7. S. Azzaro, L. Fensterbank, E. Lacôte, M. Malacria, Synlett 2008, 2253.
8. S. Azzaro, M. D.-E. Murr, L. Fensterbank, E. Lacôte, M. Malacria, Synlett 2011, 849.
9. P. H. DiChenna, F. Robert-Peillard, P. Dauban, R. H. Dodd, Org. Lett. 2004, 6, 4503.
10. F. Robert-Peillard, C. DiPablo, H. C. Liang, C. Lescot, F. Collet, R. H. Dodd, P. Dauban, Tetrahedron: Asymmetry 2010, 21, 1447.
11. C. Liang, F. Robert-Peillard, C. Fruit, P. Mueller, R. H. Dodd, P. Dauban, Angew. Chem. 2006, 118, 4757; Angew. Chem. Int. Ed. 2006, 45, 4641.
12. C. Worch, C. Bolm, Synlett 2009, 2425.
13. M. Steurer, C. Bolm, J. Org. Chem. 2010, 75, 3301.
14. H.-W. Kleemann, J. Brendel, J.-R. Schwark, A. Weichert, H. J. Lang, U. Albus, W. Scholz, (Hoechst AG, Frankfurt am Main, Germany), EP0771788A2, 1997; [Chem. Abstr. 1997, 127, 17500].
15. H.-W. Kleemann, H.-J. Lang, J.-R. Schwark, A. Weichert, W. Scholz, U. Albus, (Hoechst AG, Frankfurt am Main, Germany), US6057322A, 2000; [Chem. Abstr. 2000, 132, 293573].
16. R. Paulini, D. Breuninger, W. vonDeyn, H. M. M. Bastiaans, C. Beyer, D. D. Anspaugh, H. Oloumi-Sadeghi, (BASF SE, Ludwigshafen, Germany), WO2009/156336A1, 2009; [Chem. Abstr. 2009, 152, 97451].
17. R. Paulini, W. vonDeyn, H. M. M. Bastiaans, C. Beyer, (BASF SE, Ludwigshafen, Germany), WO2011/069955A1, 2011; [Chem. Abstr. 2011, 155, 93714].
18. B. E. Cathers, J. V. Schloss, Bioorg. Med. Chem. Lett. 1999, 9, 1527.
19. J. E. Toth, G. B. Grindey, W. J. Ehlhardt, J. E. Ray, G. B. Boder, J. R. Bewley, K. K. Klingerman, S. B. Gates, S. M. Rinzel, R. M. Schultz, L. C. Weir, J. F. Worzalla, J. Med. Chem. 1997, 40, 1018.
20. C. R. Johnson, E. U. Jonsson, C. C. Bacon, J. Org. Chem. 1979, 44, 2055.
21. S. C. Mayer, A. F. Kreft, B. Harrison, M. Abou-Gharbia, M. Antane, S. Aschmies, K. Atchison, M. Chlenov, D. C. Cole, T. Comery, G. Diamantidis, J. Ellingboe, K. Fan, R. Galante, C. Gonzales, D. M. Ho, M. E. Hoke, Y. Hu, D. Huryn, U. Jain, etal., J. Med. Chem. 2008, 51, 7348.
22. R. L. Martone, H. Zhou, K. Atchison, T. Comery, J. Z. Xu, X. Huang, X. Gong, M. Jin, A. Kreft, B. Harrison, S. C. Mayer, S. Aschmies, C. Gonzales, M. M. Zaleska, D. R. Riddell, E. Wagner, P. Lu, S.-C. Sun, J. Sonnenberg-Reines, A. Oganesian, etal., J. Pharmacol. Exp. Ther. 2009, 331, 598.
23. D. C. Cole, J. R. Stock, A. F. Kreft, M. Antane, S. H. Aschmies, K. P. Atchison, D. S. Casebier, T. A. Comery, G. Diamantidis, J. W. Ellingboe, B. L. Harrison, Y. Hu, M. Jin, D. M. Kubrak, P. Lu, C. W. Mann, R. L. Martone, W. J. Moore, A. Oganesian, D. R. Riddell, etal., Bioorg. Med. Chem. Lett. 2009, 19, 926.
24. M. S. Wolfe, Biochemistry 2006, 45, 7931.
25. J. Hardy, D. J. Selkoe, Science 2002, 297, 353.
26. M. Citron, Nat. Rev. Drug Discovery 2010, 9, 387.
27. B. DeStrooper, R. Vassar, T. Golde, Nat. Rev. Neurol. 2010, 6, 99.
28. J. Milano, J. McKay, C. Dagenais, L. Foster-Brown, F. Pognan, R. Gadient, R. T. Jacobs, A. Zacco, B. Greenberg, P. J. Ciaccio, Toxicol. Sci. 2004, 82, 341.
29. O.G. Mancheño, C. Bolm, Beilstein J. Org. Chem. 2007, 3, No. 25; DOI:.
30. P. D. Leeson, B. Springthorpe, Nat. Rev. Drug Discovery 2007, 6, 881.
31. All animal experiments were performed in accordance with relevant guidelines and regulations provided by the Swedish Board of Agriculture. The ethical permission was provided by the Stockholm Södra Animal Research Ethical Board, specialized in animal experimentations.
32. T. A. Lanz, M. J. Karmilowicz, K. M. Wood, N. Pozdnyakov, P. Du, M. A. Piotrowski, T. M. Brown, C. E. Nolan, K. E. G. Richter, J. E. Finley, Q. Fei, C. F. Ebbinghaus, Y. L. Chen, D. K. Spracklin, B. Tate, K. F. Geoghegan, L. Lau, D. D. Auperin, J. B. Schachter, J. Pharmacol. Exp. Ther. 2006, 319, 924.