442128-85-0

Upstream product

• 215300-34-8 (S)-3-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino]-1-propanoic acid methyl ester 
• 100-39-0 benzyl bromide 
• 60-18-4 L-tyrosine 
• 215596-38-6 (S)-3-(4-hydroxyphenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 442128-78-1 methyl (2S)-3-(4-benzyloxyphenyl)-2-ethoxycarbonylaminopropionate 

Downstream Products

• 1252654-20-8 (S)-4-(3-hydroxy-2-(methylamino)propyl)phenol 
• 442129-00-2 methyl N-[(2S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)propyl]aminoacetate 
• 442129-04-6 methyl N-[(2S)-3-(4-benzyloxyphenyl)-2-methylaminopropyl]aminoacetate 
• 442128-96-3 (1S)-3-(4-benzyloxyphenyl)-2-[(N)-tert-butoxycarbonyl]methylaminopropanal 
• 442129-08-0 (6S)-6-(4-benzyloxybenzyl)-1-methylpiperazin-2-one 
• 442129-12-6 (6S)-6-(4-hydroxybenzyl)-1-methylpiperazin-2-one 
• 442128-91-8 1,1-dimethylethyl N-[(1S)-2-hydroxy-1-{[4-(phenylmethoxy)phenyl]methyl}ethyl]-N-methylcarbamate 

Relevant academic research and scientific papers

Facile synthesis of enantiopure (-)-TAN1251A

Formal total synthesis of enantiopure (-)-TAN1251A, a muscarinic M1 receptor antagonist, was achieved via a spirocyclic carbon-nitrogen bond formation by the use of aromatic oxidation with bis(acetoxy)iodobenzene as a key step.

Development of Novel Monoamine Oxidase-B (MAO-B) Inhibitors with Reduced Blood-Brain Barrier Permeability for the Potential Management of Noncentral Nervous System (CNS) Diseases

Studies indicate that MAO-B is induced in peripheral inflammatory diseases. To target peripheral tissues using MAO-B inhibitors that do not permeate the blood-brain barrier (BBB) the MAO-B-selective inhibitor deprenyl was remodeled by replacing the terminal acetylene with a CO2H function, and incorporating a para-OCH2Ar motif (compounds 10a-s). Further, in compound 32 the C-2 side chain corresponded to CH2CN. In vitro, 10c, 10j, 10k, and 32 were identified as potent reversible MAO-B inhibitors, and all four compounds were more stable than deprenyl in plasma, liver microsomal, and hepatocyte stability assays. In vivo, they demonstrated greater plasma bioavailability. Assessment of in vitro BBB permeability showed that compound 10k is a P-glycoprotein (P-gp) substrate and 10j displayed mild interaction. Importantly, compounds 10c, 10j, 10k, and 32 displayed significantly reduced BBB permeability after intravenous, subcutaneous, and oral administration. These polar MAO-B inhibitors are pertinent leads for evaluation of efficacy in noncentral nervous system (CNS) inflammatory disease models.

MAO-B SELECTIVE INHIBITOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF AND USES THEREOF

Described herein are a series of compounds having the structure of Formula I for use in the inhibition of MAO and uses thereof for the treatment of a barrier disease, obesity, solid epithelial cell tumor metastasis, diabetes, an auto-immune and inflammatory disease or a cardiometabolic disorder.

A formal synthesis of a muscarinic M1 receptor antagonist, (-)-TAN1251A

An aromatic oxidation reaction of a secondary amine, prepared from L-tyrosine and glycine, with hypervalent iodine reagent gave a spirocyclic product, which was further converted into the key intermediate for the synthesis of (-)-TAN1251A.