2439-60-3

Upstream product

• 15267-95-5 chloromethyltriethoxysilane 
• 15028-44-1 DL-phenylalanine methyl ester 
• 211567-40-7 (S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-3-phenyl-propionic acid methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 74-88-4 methyl iodide 
• 191337-25-4 (S)-methyl 2-(4-nitrophenylsulphonamido)-3-phenylpropanoate 
• 1010385-05-3 C₁₈H₂₀ClNO₂ 
• 1010385-07-5 C₁₈H₂₀ClNO₂ 
• 1010385-09-7 C₁₈H₂₀N₂O₄ 
• 1010384-97-0 C₂₂H₂₃NO₂ 
• 1010384-99-2 C₂₂H₂₃NO₂ 
• 1010385-00-8 C₁₉H₂₃NO₃ 
• 1010385-02-0 C₁₉H₂₃NO₃ 
• 1010385-04-2 C₁₈H₂₀ClNO₂ 

Downstream Products

• 196928-07-1 N-(2-azidobenzoyl)-N-methyl-L-phenylalanine methyl ester 
• 216592-76-6 N-benzyloxyacetyl-N-methyl-L-phenylalanine methyl ester 
• 227616-01-5 methyl (S)-2-[(S)-2-(tert-butoxycarbonylamino)-N,4-dimethylpentanamido]-3-phenylpropanoate 
• 945670-47-3 C₂₁H₂₅NO₄ 
• 338462-77-4 (S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester 
• 1030274-24-8 C₂₀H₃₀N₂O₅ 
• 1147830-92-9 C₂₀H₂₀N₂O 

Relevant academic research and scientific papers

Toward the synthesis and improved biopotential of an n-methylated analog of a proline-rich cyclic tetrapeptide from marine bacteria

An N-methylated analog of a marine bacteria-derived natural proline-rich tetracyclopeptide was synthesized by coupling the deprotected dipeptide fragments Boc-L-prolyl-L-N-methylleucine-OH and L-prolyl-L-N-methylphenylalanine-OMe. A coupling reaction was accomplished utilizing N,N0-Dicyclohexylcarbodidimde (DCC) and 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC·HCl) as coupling agents and Triethylamine (TEA) or N-methylmorpholine (NMM) as the base in the presence of the racemization suppressing agent. This was followed by the cyclization of the linear tetrapeptide fragment under alkaline conditions. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FTIR (Fourier-transform infrared spectroscopy),1H NMR (Nuclear magnetic resonance spectroscopy),13C NMR, and mass spectrometry. From the bioactivity results, it was clear that the newly synthesized proline-rich tetracyclopeptide exhibited better anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses, and Eudrilus eugeniae at a concentration of 2 mg/mL as well as improved antifungal activity against pathogenic dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL, as compared to non-methylated tetracyclopeptide. Moreover, N-methylated tetracyclopeptide displayed significant activity against pathogenic Candida albicans.

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Postsynthetic Modification of Phenylalanine Containing Peptides by C-H Functionalization

New methods for peptide modification are in high demand in drug discovery, chemical biology, and materials chemistry; methods that modify natural peptides are particularly attractive. A Pd-catalyzed, C-H functionalization protocol for the olefination of phenylalanine residues in peptides is reported, which is compatible with common amino acid protecting groups, and the scope of the styrene reaction partner is broad. Bidentate coordination of the peptide to the catalyst appears crucial for the success of the reaction.

Insights into the Desaturation of Cyclopeptin and its C3 Epimer Catalyzed by a non-Heme Iron Enzyme: Structural Characterization and Mechanism Elucidation

AsqJ, an iron(II)- and 2-oxoglutarate-dependent enzyme found in viridicatin-type alkaloid biosynthetic pathways, catalyzes sequential desaturation and epoxidation to produce cyclopenins. Crystal structures of AsqJ bound to cyclopeptin and its C3 epimer ar

Preparation of the optically pure N-methyl amino ester method and product

The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.

Reductive N-methylation of amines with calcium hydride and Pd/C catalyst

The methylation of amines by paraformaldehyde in the presence of calcium hydride as a source of hydrogen and palladium on charcoal as catalyst was studied. Depending on the quantity of paraformaldehyde, monomethylated and dimethylated amines were selectively and efficiently prepared in one pot with good yields.

Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation

Protecting group dependant ring-closing metathesis based approach to the total synthesis of the revised structures of ciliatamides A and B has been described. The current synthetic strategy utilizes the amino acid as starting material to introduce both the stereogenic centers. However, usage of non-racemizing reagents (EDC·HCl, HATU/NMM); for amide coupling and Grubbs' second generation catalyst for caprolactam ring synthesis makes the present approach more convenient to get the correct conclusion on absolute stereochemistry. Thus, on the basis of similar optical rotation values with the Lindsley's reported data, this synthesis further supported for the actual stereochemistry of both ciliatamides A and B is (R,R).

A Common Precursor Approach to Structurally Diverse Natural Products: The Synthesis of the Core Structure of (±)-Clausenamide and the Total Synthesis of (±)-Hyalodendrin

Structurally diverse natural products from unrelated sources typically require the development of individual synthetic routes. In a novel approach, we have shown that the epidithiodiketopiperazine-derived natural product (±)-hyalodendrin and the core structure of the unrelated pyrrolidine-derived natural product clausenamide can be synthesised from a common synthetic precursor in good yield by simple variation of the reaction conditions. Structurally unrelated natural products often require individual synthetic routes. In our approach, the epidithiodiketopiperazine natural product (±)-hyalodendrin and the core structure of the unrelated pyrrolidine-derived natural product clausenamide were synthesised from a common precursor by simple variation of the reaction conditions.

2-ACYL-4-OXY-1,2-DIHYDROPYRROL-5-ONE COMPOUNDS FOR IMPROVING MEMORY AND COGNITIVE FUNCTION

The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain compounds of the following formula (for convenience, collectively referred to herein as 2-acyl-4-oxy-1,2-dihydropyrrol-5-one compounds and DHP compounds ), which, inter alia, are useful in methods of improving memory and/or cognitive function, and in the treatment of memory-related disorders and cognitive decline. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions in the treatment of central nervous system (CNS) disorders such as memory deficit, memory-related disorders, disorders associated with cognitive decline, cognitive impairment, including, for example, mild cognitive impairment (MCI), dementia, and Alzheimer's disease.

Synthesis of N-methyl L-phenylalanine for total synthesis of pepticinnamin e

The target compounds 3, 10 and 11 were synthesized through different N-methylation strategies. The concise and efficient preparation of them in large scale was developed and 3, 10 and 11 were obtained in suitable form used for both nitrogen-end and oxygen-end extension in next coupling reaction in peptides synthesis, specifically in total synthesis of natural pepticinnamin E.