18414-30-7

Usage

Uses

Used in Pharmaceutical Industry:
CIS-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals for its unique structural properties that can be leveraged to create novel drug candidates. Its cyclopentane ring and amino group in the cis configuration offer distinct chemical and biological activities, making it a valuable component in the design of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic chemistry, CIS-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID is utilized as a versatile building block for the creation of complex organic compounds. Its unique structure allows for a wide range of chemical reactions, facilitating the synthesis of diverse organic molecules with potential applications in various industries, including materials science, agrochemicals, and specialty chemicals.
Used in Drug Development Research:
CIS-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID is employed as a research tool in drug development, where its unique structural features can be explored to understand its interactions with biological targets. This knowledge can contribute to the design of more effective and selective drugs, enhancing the discovery and development of new therapeutic agents.
Used in Material Science:
In material science, CIS-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID can be incorporated into the development of novel materials with specific properties. Its cyclopentane ring and amino group may impart unique characteristics to the materials, such as improved stability, enhanced reactivity, or tailored physical properties, making it a promising component in the creation of advanced materials for various applications.

Upstream product

• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 142-29-0 cyclopentene 
• 158414-43-8 tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 3400-45-1 cyclopentanecarboxylic acid 
• 27784-73-2 tert-butyl cyclopentene-1-carboxylate 
• 87661-18-5 1,1-dimethylethyl cyclopentanecarboxylate 
• 158414-41-6 (1S,2R,αR)-tert-butyl 2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate 
• 179462-33-0 (1S,5R)-6-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 122672-46-2 (-)-cispentacin 
• 197916-36-2 ethyl (1R,2S)-2-aminocyclopentane-1-carboxylate 
• 1609100-30-2 ethyl cis-2-aminocyclopentane-1-carboxylate 
• 22031-52-3 2-aza-3-oxobicyclo<3.2.0>heptane 

Relevant academic research and scientific papers

Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy

A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies α- and alicyclic β-amino acid building blocks to construct the seven-membered heterocyclic core, while a

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

Hairpin folding behavior of mixed α/β-peptides in aqueous solution

The invention of new strategies for the design of protein-mimetic oligomers that manifest the folding encoded in natural amino acid sequences is a significant challenge. In contrast to the α-helix, mimicry of protein β-sheets is less understood. We report

New compounds

The present invention encompasses compounds of general formula (1) wherein R1, R2, R4, X, m, n and p are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.

NEW COMPOUNDS

The present invention encompassescompounds of general formula (1) wherein R1 to R4 , X and n are defined as in claim 1, which are suitable for the treatment of ailments characterised byexcessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.

Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418

A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

The first direct enzymatic hydrolysis of alicyclic β-amino esters: A route to enantiopure cis and trans β-amino acids

The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.

2,4-diamino-pyrimidines as aurora inhibitors

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.

Self-condensation of N-tert-butanesulfinyl aldimines: Application to the rapid asymmetric synthesis of biologically important amine-containing compounds

(Chemical Equation Presented) Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of frans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitrites in high-yielding concerted elimination processes.

Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.

[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lac