39629-54-4

Upstream product

• 87-69-4 L-Tartaric acid 
• 76497-43-3 (R,S)-N-methyl-β-phenyl-β-alanine 
• 81051-55-0 (Z)-ethyl 3-(methylamino)-3-phenylacrylate 
• 64-17-5 ethanol 
• 593-51-1 methylamine hydrochloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 74-89-5 methylamine 
• 4192-77-2 ethyl cinnamate 

Downstream Products

• 32975-61-4 (S)-3-methylamino-3-phenyl-propionic acid 
• 910560-67-7 (S)-3-dimethylamino-3-phenyl-propionic acid 
• 76497-43-3 (R,S)-N-methyl-β-phenyl-β-alanine 
• 122059-33-0 3-(Benzyl-methyl-amino)-3-phenyl-propionsaeureethylester 
• 150812-62-7 3-(Methoxycarbonyl-methyl-amino)-3-phenyl-propionic acid 
• 150812-65-0 3-(Benzyl-methyl-amino)-3-phenyl-propionic acid 

Relevant academic research and scientific papers

Synthesis of chiral β-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst

The organocatalysed asymmetric hydrosilylation of a number of N-aryl and alkyl β-substituted enamino esters proceeds in generally good yield and enantioselectivity. Crucial to obtaining high yield and selectivity was the addition of benzoic acid as an additive and under these conditions, both N-alkyl and N-aryl substituents were well tolerated. β-Aryl and alkyl substituents were evaluated and a model proposed to account for the experimental observations based upon enamine tautomerisation and conformational preferences of the reactive ketimine intermediate.

Synthesis and Structure-Activity Relationships of 1-Acyl-4-(2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF Antagonists

A second generation of (cyanomethyl)piperazines, 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines, with increased oral activity was prepared and evaluated in vitro in PAF-induced platelet aggregation assay (PAG) and in vivo in a PAF-induced hypotension test in normotensive rats (HYP).Oral activity was ascertained through a PAF-induced mortality test in mice (MOR).Attachment of a methyl group at position 2 of our earlier pyridine derivatives resulted in an improvement of 1 order of magnitude or greater in the ID50 of the oral test.Three different types of acylsubstituents of similar potency emerge from this work: N-(diphenylmethylamino)acetyl, 3-substituted 3-hydroxy-3-phenylpropionyl, and N-substituted 3-amino-3-phenylpropionyl groups.The most interesting compounds, 26 (UR-12460, PAG IC50 = 0.040 μM, HYP, ID50 = 0.021 mg/kg iv, MOR, ID50 = 0.30 mg/kg po) and 58 (UR-12519, PAG IC50 = 0.041 μM, HYP, ID50 = 0.015 mg/kg iv, MOR, ID50 = 0.044 mg/kg po), compare favorably with WEB-2086.Compounds 26 and 58 were also tested in active anaphylactic shock (AAS) and endotoxin-induced mortality (EIM) tests.On the basis of these data, compounds 26 and 58 have been selected for further pharmacological development.