555-29-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-alpha-methyl-DL-tyrosine is used as a potential therapeutic agent for the treatment of neurological disorders such as Parkinson's disease and attention-deficit hyperactivity disorder (ADHD). Its application is based on the hypothesis that it can help regulate neurotransmitter levels in the brain, thereby alleviating symptoms associated with these conditions.
Used in Parkinson's Disease Treatment:
In the context of Parkinson's disease, 3-Hydroxy-alpha-methyl-DL-tyrosine is considered as a prodrug for the delivery of dopamine. The rationale for its use is to potentially bypass the diminished capacity for dopamine production in the brains of Parkinson's patients, thus offering symptomatic relief and improving motor function.
Used in ADHD Treatment:
For attention-deficit hyperactivity disorder (ADHD), 3-Hydroxy-alpha-methyl-DL-tyrosine is explored as a means to modulate the levels of neurotransmitters that influence attention and impulse control. The aim is to provide a more balanced neurotransmitter environment, which may help in managing the symptoms of ADHD.

InChI:InChI=1/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m1/s1

Upstream product

• 5934-66-7 DL-N-Acetyl-α-methyl-β-<3,4-dimethoxy-phenyl>-alanin 
• 84713-76-8 2-Amino-3-(3,4-bis-benzyloxy-phenyl)-2-methyl-propionic acid ethyl ester; hydrochloride 
• 84713-73-5 3-(3,4-Bis-benzyloxy-phenyl)-2-{[1-(2,4,6-trimethyl-phenyl)-meth-(Z)-ylidene]-amino}-propionic acid ethyl ester 
• 2543-46-6 (±)-3-(3,4-dimethoxyphenyl)-2-amino-2-methylpropanenitrile 
• 16825-27-7 (S)-N-Acetyl-α-methyl-β-(3,4-dimethoxyphenyl)alanin 
• 109522-07-8 (S)-2-amino-3-(3,4-dimethoxyphenyl)-2-methylpropionamide 
• 121704-32-3 N-Chloroacetyl-α-methyl-DOPA 
• 111793-95-4 (3S,4R)-1-benzyl-3-<2-oxo-4(S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one 
• 10144-60-2 4-(3,4-dimethoxy-benzyl)-2,4-dimethyl-4H-oxazol-5-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1369423-51-7 (S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid hydrochloride 
• 1395919-79-5 (S)-3-(1-naphthoyl)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-2,2,4-trimethyloxazolidin-5-one 
• 99531-07-4 (R)-2-(3,4-Dimethoxy-benzyl)-2-methyl-malonic acid monomethyl ester 
• 5846-22-0 2-(3,4-Dimethoxy-benzyl)-2-methyl-malonic acid dimethyl ester 

Downstream Products

• 115054-62-1 α-methyl-β-3,4-dihydroxyphenyl-(L)-alanine methyl ester hydrochloride 
• 62631-37-2 (S)-N-(tert-butoxycarbonyl)-3-hydroxy-α-methyltyrosine 
• 132970-17-3 N-Boc-α-methyl-β-3,4-dimethoxyphenyl-L-alanine methylester 
• 120346-38-5 α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide 
• 79559-48-1 N-(S-benzoyl-3-mercapto-2-methylpropanoyl)-L-α-methyldopa 
• 55943-46-9 (S)-2-Amino-3-(3,4-dihydroxy-phenyl)-2-methyl-propionic acid 3-acetylamino-propyl ester 
• 753453-85-9 [Fe(HOC₆H₂(O)(CH₂C(CH₃)(NH₂)COOH)NHCC(O)N(C₆H₅)N(CH₃)C(CH₃))2(CN)(H₂O)] 
• 72634-60-7 N-(S-benzoyl-2-mercaptopropanoyl)-L-α-methyldopa 

Relevant academic research and scientific papers

Multiple molecular targets mediated antioxidant activity, molecular docking, ADMET, QSAR and bioactivity studies of halo substituted urea derivatives of α-Methyl-L-DOPA

A series of novel α-methyl-L-DOPA urea derivatives viz., 3-(3,4-dihydroxyphenyl)-2-methyl-2-(3-halo/trifluoromethyl substituted phenyl ureido)propanoic acids (6a-e) have been synthesized from the reaction of α-methyl-L-DOPA (3) with various aryl isocyanates (4a-e) by using triethylamine (5, TEA) as a base catalyst in THF at reflux conditions. The synthesized compounds are structurally characterized by spectral (IR, 1H & 13C NMR and MASS) and elemental analysis studies and screened for their in-vitro antioxidant activity against DPPH, NO and H2O2 free radical scavenging assays and identified compounds 6c & 6d as potential antioxidants. The acquired in vitro results were correlated with the results of molecular docking, ADMET, QSAR and bioactivity studies performed for them and predicted that the recorded in silico binding affinities are in good correlation with the in vitro antioxidant activity results. The molecular docking analysis has comprehended the strong hydrogen bonding interactions of 6a-e with 1CB4, 1N8Q, 3MNG, 1OG5, 1DNU, 3NRZ, 2CDU, 1HD2 and 2HCK proteins of their respective SOD, LO, PRXS5, CP450, MP, XO, NO, PRY5 and HCK enzymes. This has sustained the effective binding of 6a-e and resulted in functional inhibition of selective aminoacid residues to be pronounced as multiple molecular targets mediated antioxidant potent compounds. In addition, the evaluated toxicology risks of 6a-e are identified with in the potential limits of drug candidates. The conformational analysis of 6c & 6d prominently infers that urea moiety uniting α-methyl-L-DOPA with halo substituted aryl units into a distinctive orientation to comply good structure-activity to inhibit the proliferation of reactive oxygen species in vivo.

Synthetic method of methyldopa

The invention discloses a synthetic method of methyldopa. The method specifically comprises the steps that 3,4-dimethoxybenzaldehyde and 2-acetyl amino propionic acid methyl ester are used as raw materials, and condensation, reduction, deprotection and purification are performed. The synthetic path is simple, the yield is high, and the product purity is good.

Memory of chirality of tertiary aromatic amide: Application to the asymmetric synthesis of (S)-α-methylDOPA

We describe an original asymmetric synthesis of (S)-α-methylDOPA proceeding by the concept of memory of chirality, the only source of chirality being the starting d-alanine. The initial chirality of the amino acid is temporarily transferred to a dynamic axial chirality of a tertiary aromatic amide. The (S)-α-methylDOPA hydrochloride is obtained after four steps with 98% ee.

Polyunsaturated fatty acid derivatives, pharmaceutical compositions containing the same, method for the preparation thereof, and their use as medicament

The compounds of the Formula (I) STR1 wherein R1 is a C18-24 alkenyl containing at least two double bonds, or --(CH2)n --CH(NH2)m --COOH X is 0, NH or C1-4 alkyl-N, Y is CONH2, COOH or COOMe, wherein Me is hydrogen metal, and R2 is a side chain of a any amino acid except L-GLU or L-ASP at α-position or a group of Formula wherein k is zero or an integer of 1, n is zero or an integer of 1 to 3, m is zero or an integer of 1 to 4, A is hydroxyl or one A is hydroxyl and the other A is hydrogen. M is H or R1 --CO and X and R1 are as defined above and their salts having tyrosine kinase inhibitor activity can be used as antitumor agents.

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.

New aspects of β-lactam chemistry: β-lactams as chiral building blocks

Recent advances on the new aspects of β-lactam chemistry in which β-lactams are used as chiral building blocks for the synthesis of a variety of α-amino acids, 4α-alkyl-α-aminoacids, oligopeptides, labeled peptides, azetidines, amino alcohols, etc., are reviewed.The topics include new and effective routes to dipeptides via homochiral β-lactams obtained by extremely stereoselective cycloadditions of chiral ketenes to chiral imines, a novel route to labeled peptides through extremely stereoselective and stereospecific reductive cleavage of β-lactams on a palladium catalyst, and new efficient syntheses of α-alkyl-α-amino acids and their peptides by the highly effective asymmetric alkylations of β-lactam lithium enolates followed by hydrogenolysis or Birch reduction.Mechanism of those highly selective unique reactions are discussed.

ENZYME CATALYSED HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIESTERS, SYNTHESIS OF OPTICALLY PURE (S)-α-METHYLPHENYLALANINE, (S)-α-METHYLTYROSINE AND (S)-α-METHYL-3,4-DIHYDROXYPHENYLALANINE

Pig liver esterase and α-chymotrypsin catalysed hydrolysis of the meso-diesters 1, 2 and 3 gave the corresponding monoesters which then could be transformed into enantiomerically pure (S)-α-methylphenylalanine, (S)-α-methyltyrosine and (S)-α-methyl-3,4-dihydroxyphenylalanine.

α-Alkylation of Amino Acids without Racemization. Preparation of Either (S)- or (R)-α-Methyldopa from (S)-Alanine

Enantiomerically pure cis- and trans-5-alkyl-1-benzoyl-2-(tert-butyl)-3-methylimidazolidin-4-ones (1, 2, 11, 15, 16) and trans-2-(tert-butyl)-3-methyl-5-phenylimidazolidin-4-one (20), readily available from (S)-alanine, (S)-valine, (S)-methionine, and (R)-phenylglycine are deprotonated to chiral enolates (cf. 3, 4, 12, 21).Diastereoselective alkylation of these enolates to 5,5-dialkyl- or 5-alkyl-5-arylimidazolidinones (5, 6, 9, 10, 13a-d, 17, 18, 22) and hydrolysis give α-alkyl-α-amino acids such as (R)- and (S)-α-methyldopa (7 and 8a, resp.), (S)-α-methylvaline (14), and (R)-α-methyl-methionine (19).The configuration of the products is proved by chemical correlation and by NOE 1H-NMR measurements (see 23, 24).In the overall process, a simple, enantiomerically pure α-amino acid can be α-alkylated with retention or with inversion of configuration through pivalaldehyde acetal derivatives.Since no chiral auxiliary is required, the process is coined 'self-reproduction of a center of chirality'.The method is compared with other α-alkylations of amino acids occuring without racemization.The importance of enantiomerically pure, α-branched α-amino acids as synthetic intermediates and for the preparation of biologically active compounds is discussed.

α-METHYL AMINO ACIDS BY CATALYTIC PHASE-TRANSFER ALKYLATIONS

The α-methyl amino acids, α-methyl p-chlorophenylalanine, α-methyl p-tyrosine, α-methyl m-tyrosine and α-methyl DOPA have been prepared in good yields from amino ester hydrochlorides.The key step in the method is the catalytic phase-transfer alkylation of Schiff base derivatives of monoalkyl amino acids.