189252-75-3

Upstream product

• 189373-46-4 (R)-2-[(3,5-Dimethyl-benzoyl)-methyl-amino]-3-(4-isoxazol-5-yl-phenyl)-propionic acid ethyl ester 
• 184698-56-4 N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-alanine 
• 189373-45-3 3-[4-(5-isoxazolyl)phenyl]-(D)-alanine ethyl ester 
• 184698-53-1 3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester 
• 189252-73-1 (R)-3-(4-Isoxazol-5-yl-phenyl)-2-methylamino-propionic acid ethyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of a novel and bifunctional endothelin antagonist, IRL 3630

IRL 3630 (3), a single enantiomer of IRL 3461 with more potency was identified. Coupling reaction of the racemic fragment (1) with the chiral (L)-valinesulfonamide (2) under a biphasic solvent system (CH2Cl2-H2O) successfully led to the predominant formation of the desired isomer (3) with concomitant isomerization of 1. IRL 3630, N-butanesulfonyl-[N-(3,5- dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-(D)-alanyl]-(L)- valineamide, is a highly potent and bifunctional (ET(A)+ET(B)) antagonist [Ki(ET(A))=1.5 nM, Ki(ET(B))=1.2 nM].