441764-53-0

Upstream product

• 70681-41-3 (R)-dimethyl malate 

Downstream Products

• 441764-61-0 (R)-2-{2-[(1,1-dicyclohexylmethyl)amino]ethoxy}-succinic acid dimethyl ester 
• 441764-60-9 (R)-2-(2-cyclohexylaino-ethoxy)-succinic acid dimethyl ester 
• 441764-57-4 ((R)-3-oxo-4-phenethyl-morpholin-2-yl)acetic acid methyl ester 
• 441764-65-4 (R)-2-{2-[((S)-1-tert-butoxycarbonyl-1-phenylmethyl)amino]ethoxy}-succinic acid dimethyl ester 
• 441764-55-2 ((R)-4-benzyl-3-oxo-morpholin-2-yl)acetic acid methyl ester 
• 441764-63-2 (R)-2-{2-[(1,1-diphenylmethyl)amino]ethoxy}-succinic acid dimethyl ester 
• 609847-54-3 {(R)-3-Oxo-4-[2-phenyl-eth-(E)-ylideneamino]-morpholin-2-yl}-acetic acid methyl ester 
• 609846-51-7 [(R)-4-benzylamino-3-oxo-morpholin-2-yl]-acetic acid methyl ester 
• 609846-70-0 [(R)-3-oxo-4-phenethylamino-morpholin-2-yl]-acetic acid 
• 609846-46-0 [(R)-3-oxo-4-phenethylamino-morpholin-2-yl]-acetic acid methyl ester 
• 609846-37-9 [(R)-4-benzylamino-3-oxo-morpholin-2-yl]-acetic acid methyl ester 
• 609846-39-1 [(R)-4-benzenesulfonylamino-3-oxo-morpholin-2-yl]-acetic acid methyl ester 
• 609846-66-4 [(R)-3-oxo-4-phenylacetamido-morpholin-2-yl]-acetic acid 
• 609846-68-6 [(R)-3-oxo-4-(3-phenyl-ureido)-morpholin-2-yl]-acetic acid 

Relevant academic research and scientific papers

Enantiospecific synthesis of isomers of AES, a new environmentally friendly chelating agent

Three four-step enantiospecific syntheses of different diastereomers of AES, a new biodegradable chelating agent, are described. The stereocenters in each of the isomers are accessible from L- and D-malic and aspartic acids.

Synthesis and SAR of thrombin inhibitors incorporating a novel 4-amino-morpholinone scaffold: Analysis of X-ray crystal structure of enzyme inhibitor complex

A 4-amino-2-carboxymethyl-3-morpholinone structural motif derived from malic acid has been used to mimic D-Phe-Pro in the thrombin inhibiting tripeptide D-Phe-Pro-Arg. The arginine in D-Phe-Pro-Arg was replaced by the more rigid P1 truncated p-amidinobenzylamine (Pab). These new thrombin inhibitors were used to probe the inhibitor binding site of α-thrombin. The best candidate in this series of thrombin inhibitors exhibits an in vitro IC50 of 0.130 μM. Interestingly, the stereochemistry of the 4-amino-2-carboxymethyl-3-morpholinone motif is reversed for the most active compounds compared to that of a previously reported 2-carboxymethyl-3-morpholinone series. The X-ray crystal structure of the lead inhibitor cocrystallized with α-thrombin is discussed.

Novel morpholinone-based D-Phe-Pro-Arg mimics as potential thrombin inhibitors: design, synthesis, and X-ray crystal structure of an enzyme inhibitor complex.

A morpholinone structural motif derived from D(+)- and L(-)-malic acid has been used as a mimic of D-Phe-Pro in the thrombin inhibiting tripeptide D-Phe-Pro-Arg. In place of Arg the more rigid P1 truncated p-amidinobenzylamine (Pab) or 2-amino-5-aminomethyl-3-methyl-pyridine have been utilized. The synthetic strategy developed readily delivers these novel thrombin inhibitors used to probe the alpha-thrombin inhibitor binding site. The best candidate in this series of thrombin inhibitors exhibits an in vitro IC(50) of 720 nM. The X-ray crystal structure of this candidate co-crystallized with alpha-thrombin is discussed.