17186-56-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(S)-(+)-2-Amino-N-Methyl-3-phenyl-propionamide hydrochloride is utilized as a key intermediate in the production of various pharmaceutical and agrochemical agents. Its chiral purity ensures the synthesis of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs and agrochemicals.
Used in Medicinal Chemistry and Drug Discovery:
In the realm of medicinal chemistry, (S)-(+)-2-Amino-N-Methyl-3-phenyl-propionamide hydrochloride is employed as a versatile component in the design and synthesis of novel bioactive molecules. Its interaction with biological systems allows researchers to explore its potential in treating various diseases and conditions.
Used in Organic Synthesis as a Reagent:
(S)-(+)-2-Amino-N-Methyl-3-phenyl-propionamide hydrochloride is used as a reagent in organic synthesis, particularly for the preparation of asymmetric catalysts and chiral ligands. This application is vital for the development of enantioselective reactions, which are essential for producing enantiomerically pure compounds with specific biological activities.
Used in the Preparation of Asymmetric Catalysts:
As a component in the creation of asymmetric catalysts, (S)-(+)-2-Amino-N-Methyl-3-phenyl-propionamide hydrochloride contributes to the advancement of catalytic processes that produce chiral molecules with high enantioselectivity. This is particularly important in the synthesis of pharmaceuticals, where the desired biological activity is often associated with a specific enantiomer.
Used in the Synthesis of Chiral Ligands:
In the synthesis of chiral ligands, (S)-(+)-2-Amino-N-Methyl-3-phenyl-propionamide hydrochloride plays a significant role, providing the necessary chirality for the ligands to effectively bind to their target molecules. This is crucial in applications such as asymmetric catalysis and the development of new drugs with improved selectivity and potency.

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 74-89-5 methylamine 
• 109522-21-6 N-(t-butoxycarbonyl)-L-phenylalanine methylamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 415678-38-5 (2S,5S)-5-benzyl-3-methyl-2-phenylimidazolidin-4-one 
• 415678-38-5 5-benzyl-3-methyl-2-phenylimidazolidin-4-one 
• 854278-96-9 [(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester 
• 854278-95-8 [(1R,2S,3R,4R)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester 
• 912757-69-8 (2S,5S)-5-benzyl-2-(tert-butyl)-2,3-dimethylimidazolidin-4-one 
• 278173-23-2 (5S)-(?)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride 
• 132278-63-8 (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one 
• 145612-84-6 (9-Anthryl)CH₂CO-D-Pro-L-Phe-NHMe 

Relevant academic research and scientific papers

Modular Fragment Synthesis and Bioinformatic Analysis Propose a Revised Vancoresmycin Stereoconfiguration

Elaborate fragments of the proposed stereostructure of the complex polyketide antibiotic vancoresmycin have been synthesized in a stereoselective fashion based on a modular and convergent approach. Significant nuclear magnetic resonance differences in one of these subunits compared with the natural product question the proposed stereoconfiguration. Consequently, an extensive bioinformatics analysis of the biosynthetic gene cluster was carried out, leading to a revised stereoconfigurational proposal for this highly potent antibiotic.

Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination

We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.

Methylene-bridged bis(imidazoline)-derived 2-oxopyrimidinium salts as catalysts for asymmetric Michael reactions

In nothing flat: The title salts, having planar nitrogen centers, were utilized successfully as phase-transfer catalysts for asymmetric Michael reactions of tert-butyl glycinate benzophenone Schiff base with vinyl ketone and chalcone derivatives, thus providing excellent levels of diastereo- and enantiocontrol (see scheme). Copyright

New chiral zwitterionic phosphorus heterocycles: Synthesis, structure, properties and application as chiral solvating agents

A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods. A convenient synthetic approach to a new class of chiral zwitterionic phosphorus-containing heterocycles starting from methylene-bridged bis(imidazolines) was designed and executed. Stability and properties of the synthesized compounds were investigated. The applicability of the designed compounds as chiral solvating agents for the determination of the enantiomeric excesses of chiral acids was demonstrated. Copyright

Single-conformation and diastereomer specific ultraviolet and infrared spectroscopy of model synthetic foldamers: α/β-peptides

Resonant two-photon ionization (R2PI), UV hole-burning (UVHB), and resonant ion-dip infrared (RIDIR) spectroscopies have been used to record single-conformation infrared and ultraviolet spectra of three model synthetic foldamers with heterogeneous backbon

Chemical transformation of substrates using nonmetallic, organic catalyst compositions

A method is provided for catalytically transforming a functional group within a first reactant by reaction with a second reactant in the presence of a nonmetallic, organic catalyst composition composed of a heteroatom-containing activator and an acid, or a salt of a heteroatom-containing activator and an acid. Exemplary first reactants are α,β-unsaturated carbonyl compounds such as α,β-unsaturated ketones and α,β-unsaturated aldehydes. The heteroatom of the activator is a Group 15 or Group 16 element such as nitrogen, oxygen, sulfur or phosphorus, and exemplary heteroatom-containing activators are amines. Chiral heteroatom-containing activators can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.

Acid addition salts of imidazolidinones as reaction catalysts

Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are α,β-unsaturated carbonyl compounds such as α,β-unsaturated keto

Epoxysuccinamide derivative or salt thereof

PCT No. PCT/JP98/01778 Sec. 371 Date Dec. 17, 1998 Sec. 102(e) Date Dec. 17, 1998 PCT Filed Apr. 17, 1998 PCT Pub. No. WO98/47887 PCT Pub. Date Oct. 29, 1998The invention relates an epoxysuccinamide derivative represented by a formula (I): wherein R1 represents a hydrogen atom, an alkyl or aminoalkyl group, R2 represents an aminoalkyl group which May be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an aralkyl group which may be substituted, or an alkyl group substituted by a heterocyclic ring which may be substituted, or R1 and R2 may form a nitrogen-containing heterocyclic ring, which may be substituted, together with the adjacent nitrogen atoms, and R3 and R4 are the same or different from each other and independently represent a hydrogen atom, or an alkyl or aralkyl group, or a salt thereof, a preparation process thereof, and a medicine comprising such a derivative or salt as an active ingredient. This compound has a specific inhibitory activity for cathepsin L and family enzymes thereof, and is useful as an agent for preventing and treating metabolic osteopathy such as osteoporosis and hypercalcemia.

Matrix metalloproteinase inhibitors: A structure-activity study

Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids inaddition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (2) Potent inhibitorsmust possess string zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustratedby itsability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.