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1123172-88-2

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Discovery of cyclic sulfone hydroxyethylamines as potent and selective β-site APP-cleaving enzyme 1 (BACE1) inhibitors: Structure-based design and in vivo reduction of amyloid β-peptides
Structure-based design of a series of cyclic hydroxyethylamine BACE1 inhibitors allowed the rational incorporation of prime- and nonprime-side fragments to a central core template without any amide functionality. The core scaffold selection and the structure-activity relationship development were supported by molecular modeling studies and by X-ray analysis of BACE1 complexes with various ligands to expedite the optimization of the series. The direct extension from P1-aryl- and heteroaryl moieties into the S3 binding pocket allowed the enhancement of potency and selectivity over cathepsin D. Restraining the design and synthesis of compounds to a physicochemical property space consistent with central nervous system drugs led to inhibitors with improved blood-brain barrier permeability. Guided by structure-based optimization, we were able to obtain highly potent compounds such as 60p with enzymatic and cellular IC50 values of 2 and 50 nM, respectively, and with >200-fold selectivity over cathepsin D. Pharmacodynamic studies in APP51/16 transgenic mice at oral doses of 180 μmol/kg demonstrated significant reduction of brain Aβ levels.
Rueeger, Heinrich,Lueoend, Rainer,Rogel, Olivier,Rondeau, Jean-Michel,M?bitz, Henrik,MacHauer, Rainer,Jacobson, Laura,Staufenbiel, Matthias,Desrayaud, Sandrine,Neumann, Ulf
p. 3364 - 3386
(2012/06/01)

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Chemical Properties

Boiling Point: 315.8±42.0 °C(Predicted)
Density: 1.51±0.1 g/cm3(Predicted)
Storage Temp.:Sealed in dry,Room Temperature
PSA: 69.61000
LogP: 2.26788

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