66865-37-0

Usage

Uses

Used in Pharmaceutical Research and Development:
(2S)-Azepane-2-carboxylic acid is used as a building block for the synthesis of novel drug molecules, contributing to the development of new pharmaceuticals with unique mechanisms of action and therapeutic potential.
Used in the Study of Structure-Activity Relationships:
(2S)-Azepane-2-carboxylic acid is used as a tool in medicinal chemistry to investigate the relationship between the molecular structure of bioactive compounds and their biological activity, aiding in the optimization of drug candidates.
Used in the Development of New Materials:
(2S)-Azepane-2-carboxylic acid is used as a component in the synthesis of new materials with potential applications in various industries, such as polymers, coatings, and adhesives.
Used in Organic Synthesis:
(2S)-Azepane-2-carboxylic acid is used as a versatile intermediate in organic synthesis, enabling the preparation of a wide range of organic compounds for various applications, including pharmaceuticals, agrochemicals, and specialty chemicals.

Upstream product

• 37689-89-7 (S)-homolysine 
• 155905-76-3 (2S)-1-(tert-butoxycarbonyl)-2-azepanecarboxylic acid 
• 1034708-26-3 1-(tert-butoxycarbonyl)-azepane-2-carboxylic acid 
• 5227-53-2 (2R/S)-azepinecarboxylic acid 
• 54512-75-3 1-bromo-5-chloropentane 
• 546141-51-9 tert-butyl (3S,5S,6R)-3-(5-chloropentyl)-2-oxo-5,6-diphenyl-4-morpholinecarboxylate 
• 546141-52-0 (3S,5S,6R)-3-(5-Chloro-pentyl)-5,6-diphenyl-morpholin-2-one 
• 60274-60-4 1-chloro-5-iodopentane 
• 546141-53-1 (3R,4S,10aS)-3,4-diphenyloctahydro-1H-[1,4]oxazino-[4,3-a]azepin-1-one 
• 123053-12-3 (7S,10R)-10-(tert-butyl)-9-methyl-1,9-diazabicyclo<5.3.0>decan-8-one 
• 123053-05-4 (2S,5S)-2-tert-Butyl-5-(5-chloro-pentyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester 
• 123053-10-1 (2R,5S)-2-(tert-butyl)-5-(5-chloropentyl)-3-methyl-4-imidazolidinone 

Downstream Products

• 155905-76-3 (2S)-1-(tert-butoxycarbonyl)-2-azepanecarboxylic acid 
• 1240059-28-2 (S)-1-(4-chloro-phenyl)-azepane-2-carboxylic acid 
• 546141-58-6 C₆₄H₉₀N₄O₁₅ 
• 546141-59-7 1-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-methylamino-pentanoyloxy)-3-phenyl-propionyl]-amino}-pentanoyloxy)-propionyl]-amino}-pentanoyloxy)-3-phenyl-propionyl]-azepane-2-carboxylic acid 1-benzyloxycarbonyl-ethyl ester 
• 546141-57-5 N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-L-azepanyl-D-lactic acid 
• 546141-60-0 (S)-Azepane-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester 
• 546141-55-3 benzyl L-azepanyl-D-lactate 

Relevant academic research and scientific papers

Polybasic nitrogen heterocyclic non-natural chiral amino acid and synthesis method thereof

The invention relates to a polybasic nitrogen heterocyclic non-natural chiral amino acid and a synthesis method thereof. The amino acid can be applied to molecule building for antibiotic synthesis. According to the synthesis method, 2-aminodiethyl malonate and halogenated alkanes carry out substitution reactions, cyclization reactions, and decarboxylation reactions, and the reaction products are split to obtain the polybasic nitrogen heterocyclic non-natural chiral amino acid. The provided novel synthesis method has the advantages of simple synthesis route, low cost, convenient operation, andeasiness for commercial production, the chiral purity of obtained products is high, and the application prospect is good.

HETEROCYCLIC COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR

Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

Enzymatic synthesis of cyclic amino acids by N-methyl-l-amino acid dehydrogenase from Pseudomonas putida

A new enzymatic system for the synthesis of enantiomerically pure cyclic amino acids (CAA) from the corresponding diamino acids or racemic CAA is described. α,ω-Diamino acids were oxidized to α-keto acids with amino acid oxidases (AAO). The α-keto acids were spontaneously transformed into cyclic imino acids in the reaction medium. The resulting imines were reduced to the l-form CAA with N-methyl-l-amino acid dehydrogenase (NMAADH) from Pseudomonas putida ATCC12633 using NADPH as a cofactor. l-Form CAA were also obtained from racemic CAA using d-amino-acid oxidase and NMAADH. Using this method, a new compound [1,4]-thiazepane-3-carboxylic acid (Fig. 1) was synthesized from aminopropylcystein.

Restricted conformation analogues of an anthelmintic cyclodepsipeptide

Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.

Synthesis of Nonproteinogenic (R)- or (S)-Amino Acids. - Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert-Butyl 2-(tert-Butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI)

The enantiomerically pure glycine derivatives (R)- and (S)-Boc-BMI, commercially available on a kg scale, are used as starting materials (Scheme 1) for the preparation of (i) open-chain amino acids such as α-deuterio amino acids (4,5), β-arylalanines (2), aspartic acid derivatives (6, 7a, 8), or ω-halo amino acids (7b,c, 12, 13, 16, 17, 19, 22), (ii) of α-aminocycloalkanecarboxylic acids (9, 11), and (iii) of heterocyclic α-amino acids (14, 15, 18, 20) containing azetidine, pyrrolidine, piperidine or perhydroazepine rings.Inversion by deprotonation/protonation ordeuteration allows to prepare either enantiomer of an amino acid from the same Boc-BMI enantiomer (Scheme 5).Effects of additives such as the cyclic urea DMPU, lithium salts, or secondeary amines upon the reactivity of lithium enolates are discussed and, in part, exploited.