Home
Resources
Publications
Synthesis and Separation of the Enantiomers of the Neuropeptide S Receptor Antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic Acid 4-fluoro-benzylamide (SHA 68)

Synthesis and Separation of the Enantiomers of the Neuropeptide S Receptor Antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic Acid 4-fluoro-benzylamide (SHA 68)

Claudio Trapella, Michela Pela, Luisa Del Zoppo, Girolamo Calo, Valeria Camarda, Chiara Ruzza, Alberto Cavazzini, Valentina Costa, Valerio Bertolasi, Rainer K Reinscheid, Severo Salvadori, Remo Guerrini

J Med Chem. 2011 Apr 28;54(8):2738-44.

PMID: 21466221

Abstract:

This study reports the synthesis, chromatographic separation, and pharmacological evaluation of the two enantiomers of the neuropeptide S receptor (NPSR) antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68). The (9R)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10) and (9S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10a) were synthesized and their purity assessed by chiral chromatography. The absolute configuration of the enantiomer 10 has been assigned from the crystal structure of the corresponding (S)-phenyl ethyl amine derivative 8. Calcium mobilization studies performed on cells expressing the recombinant NPSR demonstrated that compound 10 is the active enantiomer while the contribution of 10a to the NPSR antagonist properties of the racemic mixture is negligible.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP847553893	SHA 68		847553-89-3	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: