2104-89-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-3-HYDROXY-PROPIONIC ACID METHYL ESTER is used as a building block for the synthesis of pharmaceuticals due to its ability to be incorporated into the molecular structures of various drugs, enhancing their therapeutic properties and effectiveness.
Used in Research and Development:
2-AMINO-3-HYDROXY-PROPIONIC ACID METHYL ESTER is used as a research tool for studying amino acid metabolism and biochemistry, providing insights into the fundamental processes of protein synthesis and degradation, which can lead to the discovery of new therapeutic targets and treatments.
Used in Organic Synthesis:
2-AMINO-3-HYDROXY-PROPIONIC ACID METHYL ESTER is used as a reagent in organic synthesis for the preparation of a range of chemical compounds, including those with potential applications in the medical, agricultural, and materials science fields.
Used in Drug Development:
2-AMINO-3-HYDROXY-PROPIONIC ACID METHYL ESTER is used as a precursor in the development of drugs for the treatment of various diseases and conditions, leveraging its unique chemical properties to create novel therapeutic agents with improved efficacy and safety profiles.

Upstream product

• 67-56-1 methanol 
• 302-84-1 serin 
• 56-45-1 L-serin 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 
• 312-84-5 D-Serine 
• 2104-89-4 Ser-OMe 
• 186581-53-3 diazomethane 
• 5619-04-5 methyl 2-amino-3-hydroxypropanoate hydrochloride 
• 75-36-5 acetyl chloride 
• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 

Downstream Products

• 76357-18-1 methyl 1-tritylaziridine-2-carboxylate 
• 101399-34-2 N-[N-(toluene-4-sulfonyl)-glycyl]-serine methyl ester 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 56612-65-8 2-(3,5-dioxo-1,2-diphenyl-pyrazolidin-4-ylidene)-oxazolidine-4-carboxylic acid methyl ester 
• 58861-77-1 4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 55779-32-3 serine hydroxamate 
• 82679-63-8 3-Hydroxy-2-[(E)-3-phenyl-prop-2-en-(Z)-ylideneamino]-propionic acid methyl ester 
• 78479-32-0 2-((E)-2-Benzyloxycarbonylamino-but-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-22-9 2-((E)-2-Benzyloxycarbonylamino-3-phenyl-acryloylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-19-4 2-((E)-2-Benzyloxycarbonylamino-pent-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-21-8 2-((E)-2-Benzyloxycarbonylamino-4-methyl-pent-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-20-7 2-((E)-2-Benzyloxycarbonylamino-hex-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 2104-89-4 D-serine methyl ester 
• 144001-42-3 methyl 2-(benzylamino)-3-hydroxypropanoate 

Relevant academic research and scientific papers

Simultaneous determination of serine enantiomers in plasma using Mosher's reagent and stable isotope dilution gas chromatography-mass spectrometry

D-Serine is a co-agonist of the N-methyl-D-aspartate receptor in glutamate neurotransmission and has been proposed as a potential therapeutic agent for schizophrenia. However, D-serine also acts as a nephrotoxic substance in rats at high doses. To investigate the pharmacokinetics and toxicokinetics of D-serine, a method for the stereoselective determination of serine enantiomers in rat plasma was developed using GC-MS with selected ion monitoring (GC-MS-SIM). DL-[2H3]Serine was used as an internal standard to account for losses associated with the extraction, derivatization and chromatography. Serine enantiomers were purified by cation-exchange chromatography using BondElut SCX cartridge and derivatized with HCl in methanol to form methyl ester followed by subsequent N,O-diacylation with optically active (+)-α-methoxy-α-trifluoromethylphenylacetyl chloride to form epimeric amide. Quantitation was performed by SIM of the molecular-related ions of the epimers in the chemical ionization mode. The intra- and inter-day reproducibility of the assay was less than 5% for D-serine and 3% for L-serine. The method was successively applied to study the pharmacokinetics of D-serine in rats. Copyright

Total synthesis of (-)-kainic acid and (+)-: Allo -kainic acid through SmI2-mediated intramolecular coupling between allyl chloride and an α,β-unsaturated ester

A 3,4-disubstituted pyrrolidine ring was effectively cyclized through SmI2-mediated reductive coupling between allyl chloride and an α,β-unsaturated ester, although little has been reported about SmI2-promoted C-C bond formation of an allyl chloride with an α,β-unsaturated ester. Selection of either the 3,4-cis- or 3,4-trans-selective cyclization can be accomplished simply by changing the additives from NiI2 to HMPA during reductive cyclization conducted in H2O-THF. Total synthesis of (-)-kainic acid and (+)-allo-kainic acid, which are pyrrolidine alkaloids used in neuroscience and neuropharmacology as useful molecular probes, was successfully achieved by using the stereo-complementary ring closure reactions promoted by SmI2 for the construction of the 2,3,4-trisubsituted pyrrolidine scaffold of kainoids.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols

Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).

HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF ABNORMAL CELLULAR PROLIFERATION

This invention is in the area of heterocyclic-based compounds for the treatment of disorders involving abnormal cellular proliferation, including but not limited to tumors and cancers.

A formal synthesis of (–)-kainic acid by means of SMI2-mediated radical cyclization

A formal synthesis of (–)-kainic acid (1) starting from the known D-serine derivative 9 has been established in 14 steps. Construction of all the stereogenic centers on the pyrrolidine core of 1 was successfully achieved by application of SmI2-mediated radical cyclization to the α,β-unsaturated ester having an alkyne moiety, followed by hydroxy group directed diastereoselective hydrogenation over Wilkinson’s catalyst.

Synthesis, insecticidal activities and SAR studies of novel anthranilic diamides containing trifluoroethoxyl substituent and chiral amino acid moieties

Ryanodine receptors (RyRs) activator has become one class of popular insecticide because of its unique mode of action. In order to find more new RyRs activators as insecticidal agents, a series of 18 novel chiral anthranilic diamides were designed by introducing the D-alanine acid and D-serine acid esters as well as trifluoroethoxyl group into the anthranilic diamide skeleton and synthesized successfully based on anthranilic diamide and FKI-1033 structures. The structures of the title compounds Ia–i and IIa–i were confirmed by melting points, 1H NMR, 13C NMR, elemental analysis and specific optical rotation analysis. The preliminary bioassay results indicated that most of the title compounds exhibited considerable larvicidal activities against oriental armyworm at 10 mg/L, especially Ib, Ie and IIh showed remarkable insecticidal activities at 0.5 mg/L. The larvicidal activity against diamondback moth of Ia and IId were 80% and 90% respectively at 0.0001 mg/L, which was similar to that of chlorantraniliprole. The relationship between structure and insecticidal activity was analyzed to reveal a possible co-regulated effect of the chiral amino acid ester, halogen atom or cyano group, and trifluoroethyloxyl group of the skeleton structures of the title compounds, which will provide useful information for guiding the design and discovery of new RyRs activators and insecticidal agrochemicals.

1-HETEROARYL-INDOLINE-4-CARBOXAMIDES AS MODULATORS OF GPR52 USEFUL FOR THE TREATMENT OR PREVENTION OF DISORDERS RELATED THERETO

The present invention relates to compounds of Formula (la) and pharmaceutical compositions thereof that modulate the activity of GPR52. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of a GPR52-mediated disorder (e.g., Huntington's disease, schizophrenia, bipolar disorder, attention deficit hyperactivity disorder (ADHD), or Tourette's syndrome); an extrapyramidal or movement disorder; a motor disorder; a hyperkinetic movement disorder; a psychotic disorder; catatonia; a mood disorder; a depressive disorder; an anxiety disorder; obsessive-compulsive disorder (OCD); an autism spectrum disorder; a prolactin-related disorder (e.g., hyperprolactinemia); a neurocognitive disorder; a trauma- or stressor-related disorder (e.g., posttraumatic stress disorder (PTSD)); a disruptive, impulse-control, or conduct disorder; a sleep-wake disorder; a substance-related disorder; an addictive disorder; a behavioral disorder; hypofrontality; an abnormality in the tuberoinfundibular, mesolimbic, mesocortical, or nigrostriatal pathway; decreased activity in the striatum; cortical dysfunction; neurocognitive dysfunction; and conditions related thereto.

Docking model of the nicotinic acetylcholine receptor and nitromethylene neonicotinoid derivatives with a longer chiral substituent and their biological activities

In the present study, nitromethylene neonicotinoid derivatives possessing substituents that contain a sulfur atom, oxygen atom or aromatic ring at position 5 on the imidazolidine ring were synthesized to evaluate their affinity for the nicotinic acetylcholine receptor (nAChR) and their insecticidal activity against adult female houseflies. Comparing the receptor affinity of the alkylated derivative with the receptor affinity of compounds possessing either ether or thioether groups revealed that conversion of the carbon atom to a sulfur atom did not influence the receptor affinity, whereas conversion to an oxygen atom was disadvantageous for the receptor affinity. The receptor affinity of compounds possessing a benzyl or phenyl group was lower than that of the unsubstituted compound. Analysis of the three-dimensional quantitative structure-activity relationship using comparative molecular field analysis demonstrated that steric hindrance of the receptor should exist around the C3 of an n-butyl group attached at position 5 on the imidazolidine ring. A docking study of the nAChR-ligand model suggested that the ligand-binding region expands as the length of the substituent increases by brushing against the amino acids that form the binding region. The insecticidal activity of the compounds was positively correlated with the receptor affinity by considering log P and the number of heteroatoms, including sulfur and oxygen atoms, in the substituents, suggesting that the insecticidal activity is influenced by the receptor affinity, hydrophobicity, and metabolic stability of the compounds.

Two rearrangement pathways in the geminal acylation of 2-methoxyoxazolidines leading to substituted 1,4-oxazines

Lewis acid-mediated geminal acylation of 2-methoxyoxazolidines with five- or six-membered acyloins followed by heterocyclization afforded 1,4-oxazines fused to cyclopentenone or cyclohexenone rings. Overall yields ranged from 30 to 73%. The position of the carbonyl group in the products depended on whether or not water was present during the ringexpanding acyl migration step. The route lacking water during the acyl migration step was best conducted in one pot. The addition of water effected cleavage of a silyloxy group in the intermediate during the initial Mukaiyama aldol reaction prior to the acyl migration.