142995-45-7

Basic information

• Product Name: (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(3-fluoro-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 142995-45-7
• Molecular Weight: 499.582
• Mol File: 142995-45-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(3-fluoro-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(3-fluoro-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester(142995-45-7)
• EPA Substance Registry System: (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(3-fluoro-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester(142995-45-7)

Safety Data

• Hazardous Substances Data: 142995-45-7(Hazardous Substances Data)

Upstream product

• 142995-36-6 Boc-Phe(3-F)-NMeBzl 
• 114873-01-7 N-Boc-3-fluoro-L-phenylalanine 
• 19883-77-3 L-3-fluorophenylalanine 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds

As an extension of our studies on discovering a novel substance P (SP) antagonist, we modified the previously reported dipeptide, N2-2-(1H-indol-3-ylcarbonyl)-L-lysyl>-N-methyl-N-(phenylmethyl)-L-phenylalaninamide (2b).The lysine part in 2b was first optimized to a (2S,4R)-hydroxyproline derivative (3h), which is 2-fold more potent than 2b in SP binding assay using guinea pig lung membranes.Next we modified the 1H-indol-3-ylcarbonyl part in 3h.Introduction of a methyl group at the indole nitrogen enhanced the oral activity, while retaining the binding activity.Finally, we modified the phenylalanine part to culminate in the most potent compound 7k (FK888), which is a potent SP antagonist with NK1 selectivity as well as oral activity.