Stereo-controlled synthesis of novel photoreactive γ-secretase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 3, 2009, Pages 922-925

  Yang, Guangli ^a   Yin, Ye Ingrid ^a   Chun, Jiong ^a   Shelton, Christopher C ^a   Ouerfelli, Ouathek ^a   Li, Yue Ming ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

Alzheimer disease; Aspartyl proteases; Dipeptide isostere; Photoaffinity labeling; Secretase

Indexed keywords

GAMMA SECRETASE; GAMMA SECRETASE INHIBITOR; L 685458; PRESENILIN 1; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; ENZYME ACTIVE SITE; HUMAN; HUMAN CELL; IC 50; PHOTOREACTIVITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALZHEIMER DISEASE; AMYLOID PRECURSOR PROTEIN SECRETASES; BIOTINYLATION; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; DRUG DESIGN; EPOXY COMPOUNDS; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LACTONES; MODELS, CHEMICAL; PHOTOCHEMISTRY; PRESENILIN-1;

EID: 58549103492     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.117     Document Type: Article

References (22)

1. Hardy J., and Allsop D. Trends Pharmacol. Sci. 12 (1991) 383
2. De Strooper B. Neuron 38 (2003) 9
3. Wolfe M.S., Xia W., Ostaszewski B.L., Diehl T.S., Kimberly W.T., and Selkoe D.J. Nature 398 (1999) 513
4. Li Y.M., Xu M., Lai M.T., Huang Q., Castro J.L., DiMuzio-Mower J., Harrison T., Lellis C., Nadin A., Neduvelil J.G., Register R.B., Sardana M.K., Shearman M.S., Smith A.L., Shi X.P., Yin K.C., Shafer J.A., and Gardell S.J. Nature 405 (2000) 689
5. Esler W.P., Kimberly W.T., Ostaszewski B.L., Diehl T.S., Moore C.L., Tsai J.Y., Rahmati T., Xia W., Selkoe D.J., and Wolfe M.S. Nat. Cell Biol. 2 (2000) 428
6. Sherrington R., Rogaev E.I., Liang Y., Rogaeva E.A., Levesque G., Ikeda M., Chi H., Lin C., Li G., Holman K., et al. Nature 375 (1995) 754
7. Wolfe M.S., and Kopan R. Science 305 (2004) 1119
8. Brown M.S., Ye J., Rawson R.B., and Goldstein J.L. Cell 100 (2000) 391
9. Shearman M.S., Beher D., Clarke E.E., Lewis H.D., Harrison T., Hunt P., Nadin A., Smith A.L., Stevenson G., and Castro J.L. Biochemistry 39 (2000) 8698
10. Chun J., Yin Y.I., Yang G., Tarassishin L., and Li Y.M. J. Org. Chem. 69 (2004) 7344
11. Chen P., Cheng P.T.W., Spergel S.H., Zahler R., Wang X.B., Thottathil J., Barrish J.C., and Polniaszek R.P. Tetrahedron Lett. 38 (1997) 3175
12. Chai W., and Murray W.V. Tetrahedron Lett. 40 (1999) 7185
13. Orito K., Sato S., and Suginome H. J. Chem. Soc., Perkin Trans. 1 1 (1995) 63
14. 4Na: 506.2703, found 506.2698.
15. Evans B.E., Rittle K.E., Homnick C.F., Springer J.P., Hirshfield J., and Veber D.F. J. Org. Chem. 50 (1985) 4615
16. Nadin A., Lopez J.M.S., Neduvelil J.G., and Thomas S.R. Tetrahedron 57 (2001) 1861
17. 5Na: 524.2413, found 524.2402.
18. Fauq A.H., Cherif-Ziani C., and Richelson E. Tetrahedron: Asymmetry 9 (1998) 2333
19. 5Na: 522.2256, found 522.2250.
20. Kokotos G., Padrón J.M., Martín T., Gibbons W.A., and Martín V.S. J. Org. Chem. 63 (1998) 3741
21. 8: 792.4224, found 792.4229.
22. Li Y.M., Lai M.T., Xu M., Huang Q., DiMuzio-Mower J., Sardana M.K., Shi X.P., Yin K.C., Shafer J.A., and Gardell S.J. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 6138