(2S)-S-(5-chlorothiophen-2-yl)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butane-2-sulfonamido

• ChemBase ID: 169780
• Molecular Formular: C9H8ClF6NO3S2
• Molecular Mass: 391.7381392
• Monoisotopic Mass: 390.95383212
• SMILES: S(=O)(=O)(N[C@@H](C(C(F)(F)F)C(F)(F)F)CO)c1ccc(s1)Cl
• Canonical SMILES: OC[C@H](C(C(F)(F)F)C(F)(F)F)NS(=O)(=O)c1ccc(s1)Cl
• InChI: InChI=1S/C9H8ClF6NO3S2/c10-5-1-2-6(21-5)22(19,20)17-4(3-18)7(8(11,12)13)9(14,15)16/h1-2,4,7,17-18H,3H2/t4-/m1/s1
• InChIKey: PSXOKXJMVRSARX-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-S-(5-chlorothiophen-2-yl)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butane-2-sulfonamido
• IUPAC Traditional name: begacestat
• Synonyms: 5-Chloro-N-[(1S)-3,3,3-trifluoro-1-(hydroxymethyl)-2-(trifluoromethyl)propyl]-2-thiophenesulfonamide; Begacestat; GSI 953; GSI-953

Database IDs

• CAS Number: 769169-27-9
• PubChem SID: 162263912
• PubChem CID: 11269353

CALCULATED PROPERTIES

• Acid pKa: 8.191627
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4232254
• LogD (pH = 7.4): 2.364987
• Log P: 2.4240317
• Molar Refractivity: 64.7631 cm^3
• Polarizability: 25.799778 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G797400

Begacestat (GSI-953) is a selective β-secretase inhibitor that selectively inhibits cleavage of APP over Notch. GSI-953 is used for treating diseases such as cancer in relation to prevention of intestinal secretory metaplasia.

REFERENCES

• van Es., et al.: Nature, 435, 959 (2005)
• Morohashi., et al.: J. Biol. Chem., 281, 1467 (2005)
• O'Neil., et al.: Neoplasia, 107, 781 (2005)
• Mayer, et al.: J. Med. Chem., 51, 7348 (2005)
• Martone, et al.: J. Pharmacol. Exp. Ther., 331, 598 (2005)