105608-78-4

Basic information

• Product Name: 3-Amino-1-fluoro-4-phenyl-butan-2-ol
• Synonyms: 3-Amino-1-fluoro-4-phenyl-butan-2-ol
• CAS NO: 105608-78-4
• Molecular Formula: C₁₀H₁₄FNO
• Molecular Weight: 183.2226632
• Mol File: 105608-78-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Amino-1-fluoro-4-phenyl-butan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-1-fluoro-4-phenyl-butan-2-ol(105608-78-4)
• EPA Substance Registry System: 3-Amino-1-fluoro-4-phenyl-butan-2-ol(105608-78-4)

Safety Data

• Hazardous Substances Data: 105608-78-4(Hazardous Substances Data)

Upstream product

• 56271-33-1 3-phenyl-2-(phthalimido)propanoyl chloride 
• 106943-09-3 N-<3-Fluoro-2-hydroxy-1-(phenylmethyl)propyl>phthalimide 
• 123003-98-5 N-<3-Bromo-2-oxo-1-(phenylmethyl)propyl>phthalimide 
• 123003-99-6 N-<3-Fluoro-2-oxo-1-(phenylmethyl)propyl>phthalimide 
• 98847-93-9 N-<3-Diazo-2-oxo-1-(phenylmethyl)propyl>phthalimide 
• 6125-24-2 2-Phenylnitroethane 
• 5153-67-3 nitrostyrene 
• 102195-94-8 1-Fluoro-2-hydroxy-3-nitro-4-phenylbutane 

Downstream Products

• 197855-42-8 [(S)-1-(1-Benzyl-3-fluoro-2-hydroxy-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 1359852-40-6 methyl 8-((2S)-1-(4-fluoro-3-hydroxy-1-phenylbutan-2-ylamino)-3-methyl-1-oxobutan-2-ylamino)-8-oxooctanoate 
• 197855-46-2 (S)-2-(3-Benzyl-ureido)-4-methyl-pentanoic acid (1-benzyl-3-fluoro-2-hydroxy-propyl)-amide 
• 209664-38-0 (R)-4-Methyl-2-[2-oxo-2-(9H-xanthen-9-yl)-ethyl]-pentanoic acid (1-benzyl-3-fluoro-2-hydroxy-propyl)-amide 
• 197855-47-3 3,4-Dihydro-1H-isoquinoline-2-carboxylic acid [(S)-1-(1-benzyl-3-fluoro-2-hydroxy-propylcarbamoyl)-3-methyl-butyl]-amide 
• 197855-45-1 (S)-4-Methyl-2-(morpholine-4-sulfonylamino)-pentanoic acid (1-benzyl-3-fluoro-2-hydroxy-propyl)-amide 

Relevant articles and documents

Synthesis and biological activity of a series of potent fluoromethyl ketone inhibitors of recombinant human calpain I

Calpain I, an intracellular cysteine protease, has been implicated in the neurodegeneration following an episode of stroke. In this paper, we report on a series of potent dipeptide fluoromethyl ketone inhibitors of recombinant human calpain I (rh calpain I). SAR studies revealed that while calpain I tolerates a variety of hydrophobic groups at the P1 site, Leu at P2 is preferred. However, the nature of the N-terminal capping group has a significant effect on the inhibitory activity of this series of compounds. Compound 4e [(1,2,3,4-tetrahydroisoquinolin-2-yl)carbonyl-Leu-D,L-Phe- CH2F], having a tetrahydroisoquinoline containing urea as the N-terminal capping group, is the most potent dipeptide fluoromethyl ketone inhibitor of calpain 1 (with a second-order rate constant for inactivation of 276 000 M- 1 s-1) yet reported; tripeptide 4k (Cbz-Leu-Leu-D,L-Phe-CH2F) is equipotent. A number of compounds presented in this study displayed excellent selectivity for calpain I over cathepsins B and L, two related cysteine proteases. Compounds which exhibited good inhibitory activity in the assay against isolated rh calpain I also inhibited intracellular calpain I in a human cell line. Thus, in an intact cell assay, compounds 4e and 4k inhibited calpain I with IC50 values of 0.2 and 0.1 μM, respectively. Finally, we also disclose the first example of fluorination of a dipeptide enol silyl ether to generate the corresponding dipeptide fluoromethyl ketone.

Synthesis of Fluorinated α-Amino Ketones, III. Preparation of Fluorinated Ketone Analogues of Phenylalanine, Lysine, and p-(Guanidino)phenylalanine

The synthesis of α-amino mono-, di-, and trifluoromethyl and difluoromethylene ketones and their derivatives is described.A one-pot sequence related to the Dakin-West reaction starts from amino acids and gives the corresponding fluorinated ketone analogue