21705-13-5

Usage

Uses

Used in Organic Synthesis:
Methyl D-alaninate is used as a reagent in organic synthesis for the preparation of various compounds, including pharmaceuticals and chemicals. Its role as a chiral building block is crucial in the synthesis of chiral compounds, which are essential in the development of enantiomerically pure drugs and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl D-alaninate is utilized as a key intermediate in the synthesis of chiral drugs. Its chiral properties allow for the creation of enantiomerically pure compounds, which are vital for the development of effective and safe medications.
Used in Agrochemical Industry:
Methyl D-alaninate also finds applications in the agrochemical industry, where it is used in the synthesis of chiral agrochemicals. These chiral compounds can exhibit improved selectivity and reduced environmental impact compared to their racemic counterparts.
Used in Food and Beverage Industry:
In the food and beverage industry, methyl D-alaninate is employed as a flavor and fragrance ingredient. Its fruity odor and solubility in water and polar organic solvents make it suitable for use in a variety of food and beverage products, enhancing their sensory characteristics.

InChI:InChI=1/C4H9NO2/c1-3(5)4(6)7-2/h3H,5H2,1-2H3/p+1/t3-/m1/s1

Upstream product

• 67-56-1 methanol 
• 144202-80-2 6,6'-bis(α-alanylamino)-2,2'-bipyridine 
• 5634-53-7 methyl pyruvate oxime 
• 101137-66-0 methyl2-<(E)-phenylhydrazono>propionate 
• 77714-26-2 2-((E)-3-Oxo-propenylamino)-propionic acid methyl ester 
• 5199-50-8 methyl 2-iodoacetate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 302-72-7 rac-Ala-OH 
• 112392-66-2 methyl 2-{[(tert-butoxy)carbonyl]amino}propanoate 
• 75-77-4 chloro-trimethyl-silane 
• 7625-53-8 rac-Ala-OMe 
• 87900-23-0 (S)-2-tert-Butyl-3,6-dimethoxy-5-methyl-2,5-dihydro-pyrazine 

Downstream Products

• 100616-49-7 N-(N-phenylsulfanylcarbonyl-glycyl)-alanine methyl ester 
• 22221-80-3 N-(N-benzyloxycarbonyl-L-leucyl)-D-alanine methyl ester 
• 1803-59-4 N-benzyloxycarbonyl-L-leucyl-L-alanine methyl ester 
• 2508-25-0 DL-alanine hydroxamic acid 
• 5625-46-7 cyclo(-DL-Ala-DL-Ala-) 
• 159721-22-9 N-benzyl-alanine methyl ester 
• 115294-42-3 N-phenoxycarbonyl-alanine methyl ester 
• 61298-93-9 C₁₃H₁₆N₂O₅S 
• 34757-14-7 methyl 2-diazopropanoate 
• 17344-99-9 AlaOEt 
• 126686-69-9 disulfide dimer of Boc-L-Cys-(D,L)-Ala-OMe 
• 130568-27-3 N-(Benzyloxycarbonylamino ethyl ethoxyphosphinyl)-alanine methyl ester 
• 133981-25-6 C₂₀H₂₅N₂O₅P 
• 133981-26-7 C₂₃H₃₁N₂O₅P 

Relevant academic research and scientific papers

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.

Resveratrol amino acid ester derivative and preparation method thereof

The invention discloses a resveratrol amino acid ester derivative and a preparation method thereof, and belongs to the technical field of fine chemical substance synthesis. The structure of the resveratrol amino acid ester derivative is represented by a formula shown in the description. The resveratrol amino acid ester derivative is synthesized from resveratrol, R amino acid, R' alcohol, dichlorosulfoxide and di(p-nitrobenzene) carbonate with 4-dimethylaminopyridine (DMAP) as a catalyst and acetonitrile as a solvent, wherein the R amino acid is one of alpha-alanine, beta-alanine and gamma-aminobutyric acid, and the R' alcohol is one of methanol, ethanol and n-propanol. The technical problem that resveratrol is difficult to preserve is solved, the pharmacological toxicity introduced by a resveratrol substituent group is lowered, and the resveratrol amino acid ester derivative has the pharmaceutical effects of resveratrol and amino acid. It is expected that the above novel compound playsa great role in beauty treatment and production of fatigue-relieving and blood pressure-lowering medicines.

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.

Structure-Guided Design and Development of Potent and Selective Dual Bromodomain 4 (BRD4)/Polo-like Kinase 1 (PLK1) Inhibitors

The simultaneous inhibition of polo-like kinase 1 (PLK1) and BRD4 bromodomain by a single molecule could lead to the development of an effective therapeutic strategy for a variety of diseases in which PLK1 and BRD4 are implicated. Compound 23 has been found to be a potent dual kinase-bromodomain inhibitor (BRD4-BD1 IC50 = 28 nM, PLK1 IC50 = 40 nM). Compound 6 was found to be the most selective PLK1 inhibitor over BRD4 in our series (BRD4-BD1 IC50 = 2579 nM, PLK1 IC50 = 9.9 nM). Molecular docking studies with 23 and BRD4-BD1/PLK1 as well as with 6 corroborate the biochemical assay results.

Imines derived from 4-methyl-4-diphenylphosphorylpentan-2-one and potassium salts of aminocarboxylic acids

An effective procedure for the preparation of imines based on 4-methyl-4-diphenylphosphorylpentan-2-one, aminoacetic, aminopropionic, and aminobutyric acids with yields of 90–95% was developed. Reaction of dimephosphone (4-methyl-4-dimethoxyphosphorilpent

Chiral phosphorescent probes for amino acids: hybrids of iridium(iii) complexes with synthetic saponite

An attempt of developing a chiral luminescent probe for amino acids was described. Two types of chiral iridium(iii) complexes were synthesized: [Ir(dfppy)2(R-pep-bpy)]+ (dfppyH = 2-(2′,4′-difluorophenyl)pyridine); R-pep-bpy = 4,4′-bis((R-1,2-dimethylpropyl)aminocarbonyl-2,2′-bipyridine) and [Ir(piq)2(R-pep-bpy)]+ (piqH = 1-phenyisoquinoline). In both complexes, amido groups (R-pep-) were attached to 2,2′-bipyridine with an intension of increasing the affinity for an amino acid. The complexes were optically resolved on a chiral column. When the complexes were adsorbed by the colloidal particles of synthetic saponite, they were highly emissive even in a medium containing water. The remarkable quenching of emission was observed for the combination of [Ir(dfppy)2(R-pep-bpy)]+ and tryptophan methyl ester. By the use of the enantiomeric complexes, the possibility of enantioselective quenching was examined for various amino acid derivatives.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Synthesis and biological evaluation of novel lipoamino acid derivatives

Seven novel lipoamino acid conjugates were synthesized from methyl oleate and amino acids. Methyl oleate was grafted to different amino acids using thioglycolic acid as a spacer group. Seven derivatives (3a-g) were prepared and characterized by spectral data (NMR, IR and MS spectral studies). All the derivatives were studied for their antimicrobial, anti-biofilm and anticancer activities. Among all the derivatives, it was found that compound 3b was the most potent antibacterial compound which showed good activity against four Gram positive bacterial strains and also exhibited excellent antifungal activity against a fungal strain. In the anti-biofilm assay, compound 3b showed promising activity with IC50 value of 2.8 μM against Bacillus subtilis MTCC 121. All the compounds showed anticancer activities with 3c showing promising anticancer activity (IC50 = 15.3-22.4 μM) against the four cell lines tested.

Design, synthesis of new chiral fluorine-containing β-hydroxysulfonamides from natural amino acids and study of their anti-inflammatory and analgesic activities

A series of new chiral fluorine-containing β-hydroxysulfonamides were conveniently synthesized in three steps, starting from natural L-amino acids, and evaluated for their anti-inflammatory and analgesic activities. The structures of these compounds were supported by FT-IR, 1H, 13C and 19F NMR, elemental analysis and HRMS. Among the tested compounds, 4c, 4g and 4h exhibited promising anti-inflammatory activity. Moreover, compound 4h showed a significant analgesic activity. The structure–activity relationships of selected compounds were discussed.

P2X3 AND/OR P2X2/3 COMPOUNDS AND METHODS

The present application provides novel compounds and methods for preparing and using these compounds. In one embodiment, the compounds are of the structure of formula (I), wherein R1-R4 are defined herein. In a further embodiment, these compounds are useful in method for regulating one or both of the P2X3 or P2X2/3 receptors. In another embodiment, these compounds are useful for treating pain in patients by administering one or more of the compounds to a patient.