662
Views
7
CrossRef citations to date
0
Altmetric
Research Article

Synthesis and biological activity of N-substituted spiro[benzoxazepine-piperidine] Aβ-peptide production inhibitors

, , , &
Pages 996-1001 | Received 16 May 2007, Accepted 29 Jun 2007, Published online: 20 Oct 2008

References

  • Y Gong, L Chang, KL Viola, PN Lacor, MP Lambert, CE Finch, GA Krafft, WL Klein. Alzheimer's disease-affected brain: Presence of oligomeric A beta ligands (ADDLs) suggests a molecular basis for reversible memory loss. Proc Natl Acad Sci USA (2003); 100(18):10417–10422.
  • ER Siemers, JF Quinn, J Kaye, MR Farlow, A Porsteinsson, P Tariot, P Zoulnouni, JE Galvin, DM Holtzman, DS Knopman, et al. Effects of a gamma-secretase inhibitor in a randomized study of patients with Alzheimer disease. Neurology (2006); 66(4):602–604.
  • HF Dovey, V John, JP Anderson, LZ Chen, PD Andrieu, LY Fang, SB Freedman, B Folmer, E Goldbach, EJ Holsztynska, et al. Functional gamma-secretase inhibitors reduce beta-amyloid peptide levels in brain. J Neurochem (2001); 76(1):173–181.
  • B Schmidt. Aspartic proteases involved in Alzheimer's disease. Chembiochem (2003); 4(5):366–378.
  • T Kan, Y Tominari, K Rikimaru, Y Morohashi, H Natsugari, T Tomita, T Iwatsubo, T Fukuyama. Parallel synthesis of DAPT derivatives and their g-secretase-inhibitory activity. Bioorg Med Chem Lett (2004). 14(8):1983–1985.
  • CVC Prasad, S Vig, W Smith David, Q Gao, T Polson Craig, A Corsa Jason, L Guss Valerie, A Loo, M Barten Donna, M Zheng, et al. 2,3-Benzodiazepin-1,4-diones as peptidomimetic inhibitors of gamma-secretase. Bioorg Med Chem Lett (2004); 14(13):3535–3538.
  • G Larbig, A Zall, B Schmidt. Inhibitors designed for presenilin 1 by means of aspartic acid activation: Preliminary communication. Helv Chim Acta (2004); 87(9):2334–2340.
  • GT Wong, D Manfra, FM Poulet, Q Zhang, H Josien, T Bara, L Engstrom, M Pinzon-Ortiz, JS Fine, HJ Lee, et al. Chronic treatment with the gamma-secretase inhibitor LY-411,575 inhibits beta-amyloid peptide production and alters lymphopoiesis and intestinal cell differentiation. J Biol Chem (2004); 279(13):12876–12882.
  • MJ Mokrosz, B Duszynska, AJ Bojarski, JL Mokrosz. Structure-activity relationship studies of CNS agents–XVII. Spiro[piperidine-4′,1-(1,2,3,4-tetrahydro-beta-carboline)] as a probe defining the extended topographic model of 5-HT1A receptors. Bioorg Med Chem (1995); 3(5):533–538.
  • L Yang, G Morriello, K Prendergast, K Cheng, T Jacks, WW Chan, KD Schleim, RG Smith, AA Patchett. Potent 3-spiropiperidine growth hormone secretagogues. Bioorg Med Chem Lett (1998); 8(1):107–112.
  • M Rosini, V Andrisano, M Bartolini, ML Bolognesi, P Hrelia, A Minarini, A Tarozzi, C Melchiorre. Rational approach to discover multipotent anti-Alzheimer drugs. J Med Chem (2005); 48(2):360–363.
  • L Packer, EH Witt, HJ Tritschler. Alpha-lipoic acid as a biological antioxidant. Free Radic Biol Med (1995); 19(2):227–250.
  • L Packer. Alpha-lipoic acid: A metabolic antioxidant which regulates NF-kappa B signal transduction and protects against oxidative injury. Drug Metab Rev (1998). 30(2):245–275.
  • K Hager, A Marahrens, M Kenklies, P Riederer, G Munch. Alpha-lipoic acid as a new treatment option for Azheimer type dementia. Arch Gerontol Geriatr (2001); 32(3):275–282.
  • Y Laras, N Pietrancosta, V Moret, S Marc, C Garino, A Rolland, V Monnier, J Kraus. Synthesis of new substituted 4,5-dihydro-3h-spiro[1,5]-benzoxazepine-2,4′-piperidine and biological properties. Aust J Chem (2006); 59(11):812–818.
  • G Campiani, S Butini, F Trotta, C Fattorusso, B Catalanotti, F Aiello, S Gemma, V Nacci, E Novellino, JA Stark, et al. Synthesis and pharmacological evaluation of potent and highly selective D3 receptor ligands: Inhibition of cocaine-seeking behavior and the role of dopamine D3/D2 receptors. J Med Chem (2003); 46(18):3822–3839.
  • M Govoni, RA Bakker, I van de Wetering, MJ Smit, WM Menge, H Timmerman, S Elz, W Schunack, R Leurs. Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists. J Med Chem (2003); 46(26):5812–5824.
  • N Pietrancosta, G Quelever, Y Laras, C Garino, S Burlet, JL Kraus. Design of beta-secretase inhibitors by introduction of a mandelyl moiety in DAPT analogues. Aust J Chem (2005); 58(8):585–594.
  • PR Andres, R Lunkwitz, GR Pabst, K Bohn, D Wouters, S Schmatloch, US Schubert. New 4′-functionalized 2,2′: 6′,2″-terpyridines for applications in macromolecular chemistry and nanoscience. Eur J Org Chem (2003); (19):3769–3776.
  • T Tomita, K Maruyama, TC Saido, H Kume, K Shinozaki, S Tokuhiro, A Capell, J Walter, J Grunberg, C Haass, et al. The presenilin 2 mutation (N141I) linked to familial Alzheimer disease (Volga German families) increases the secretion of amyloid beta protein ending at the 42nd (or 43rd) residue. Proc Natl Acad Sci USA (1997); 94(5):2025–2030.
  • A Asami-Odaka, Y Ishibashi, T Kikuchi, C Kitada, N Suzuki. Long amyloid b-protein secreted from wild-type human neuroblastoma IMR-32 cells. Biochemistry (1995); 34(32):10272–10278.
  • M Ito, S Yamamoto, K Nimura, K Hiraoka, K Tamai, Y Kaneda. Rad51 siRNA delivered by HVJ envelope vector enhances the anti-cancer effect of cisplatin. J Gene Med (2005). 7(8):1044–1052.
  • LD Plant, JP Boyle, IF Smith, C Peers, HA Pearson. The production of amyloid beta peptide is a critical requirement for the viability of central neurons. J Neurosci (2003); 23(13):5531–5535.
  • M Hellstrom, LK Phng, JJ Hofmann, E Wallgard, L Coultas, P Lindblom, J Alva, AK Nilsson, L Karlsson, N Gaiano, et al. Dll4 signalling through Notch1 regulates formation of tip cells during angiogenesis. Nature (2007); 445(7129):776–780.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.