106089-24-1

Basic information

• Product Name: (R)-1-Methacryloylpyrrolidine-2-carboxylic acid
• Synonyms: (R)-1-Methacryloylpyrrolidine-2-carboxylic acid
• CAS NO: 106089-24-1
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20442
• Mol File: 106089-24-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-1-Methacryloylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Methacryloylpyrrolidine-2-carboxylic acid(106089-24-1)
• EPA Substance Registry System: (R)-1-Methacryloylpyrrolidine-2-carboxylic acid(106089-24-1)

Safety Data

• Hazardous Substances Data: 106089-24-1(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
(R)-1-Methacryloylpyrrolidine-2-carboxylic acid is used as a monomer for the synthesis of polymers and copolymers, particularly in the formation of crosslinked polymer networks. Its ability to undergo radical polymerization is crucial for creating materials with specific properties for various applications.
Used in Coatings and Adhesives Industry:
In the coatings and adhesives industry, (R)-1-Methacryloylpyrrolidine-2-carboxylic acid is used as a component in the formulation of high-performance coatings and adhesives. The crosslinked polymer networks formed from (R)-1-Methacryloylpyrrolidine-2-carboxylic acid contribute to the durability and stability of these products.
Used in Biomedical Materials:
(R)-1-Methacryloylpyrrolidine-2-carboxylic acid is utilized as a key component in the development of biomedical materials due to its biocompatibility and the ability to form polymers with tailored properties for medical applications, such as drug delivery systems and tissue engineering scaffolds.
Used in Pharmaceutical Development:
The chiral recognition and biological activity of (R)-1-Methacryloylpyrrolidine-2-carboxylic acid make it a valuable compound in the pharmaceutical industry. It is used as a building block for the synthesis of chiral drugs and as a component in drug delivery systems that require specific targeting and release profiles.
Used in Electronic and Optoelectronic Devices:
(R)-1-Methacryloylpyrrolidine-2-carboxylic acid is employed in the fabrication of functional materials for electronic and optoelectronic devices. Its unique properties allow for the creation of materials with specific electronic and optical characteristics, enhancing the performance of these devices.

Upstream product

• 344-25-2 D-Prolin 
• 920-46-7 Methacryloyl chloride 
• 1634-04-4 tert-butyl methyl ether 
• 35595-88-1 1-(2-methyl-1-oxo-2-propenyl)pyrrolidine 

Downstream Products

• 927203-28-9 (3R,8αR)-3-(bromomethyl)-3-methyl-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 927203-28-9 (3R,8R)-3-Bromomethyl-3-methyl-tetrahydropyrolo[2,1-c][1,4]oxazine-1,4-dione 
• 261904-39-6 (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid 
• 106138-80-1 (3R,8AR)-3-Bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 927203-28-9 3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 

Relevant articles and documents

Synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as SARMs

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Synthesis of oxazolidinedione derived bicalutamide analogs

The synthesis of chiral oxazolidinedione derived bicalutamide analogs has been discussed.

Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.

Meta -Non-flat substituents: A novel molecular design to improve aqueous solubility in small molecule drug discovery

Aqueous solubility is a key requirement for small-molecule drug candidates. Here, we investigated the regioisomer-physicochemical property relationships of disubstituted benzenes. We found that meta-isomers bearing non-flat substituents tend to possess the lowest melting point and the highest thermodynamic aqueous solubility among the regioisomers. The examination of pharmaceutical compounds containing a disubstituted benzene moiety supported the idea that the introduction of a non-flat substituent at the meta position of a benzene substructure would be a promising approach for medicinal chemists aiming to improve the thermodynamic aqueous solubility of drug candidates, even though it might not be universally effective. This journal is

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

This invention is directed to selective androgen receptor degrader (SARD) compounds including heterocyclic rings and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedys disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

Synthetic method of alpha-hydroxypropanamide derivatives with optical activity

The invention discloses a synthetic method of alpha-hydroxypropanamide derivatives with optical activity and belongs to the field of organic synthesis. Proline taken as a chiral auxiliary, as well asmethacryloyl chloride, is subjected to acylation, bromination and chiral auxiliary removal, a product and 4-cyano-3-trifluoromethylaniline are subjected to nucleophilic substitution, and 3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]propanamide is obtained and subjected to nucleophilic substitution with 4-cyanophenol, and the compound 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. 3-bromo-2-hydroxy-2-methyl propionic acid and 4-nitro-3-trifluoromethylaniline are subjected to aminolysis, a product is subjected to nucleophilic substitution with paracetamol, and the compound 3-(4-acetoxyphenoxy)-N-[4-nitro-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. The efficient synthetic method of the alpha-hydroxypropanamide derivatives with optical activity is provided.

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

This invention is directed to selective androgen receptor degrader (SARD) compounds including heterocyclic rings and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedys disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

Synthetic method for (2R)-3-bromo-2-hydroxy-2-methylpropionic acid

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SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

This invention is directed to pyrrole, pyrazole, imidazole, triazole, and morpholine based selective androgen receptor degrader (SARD) compounds including heterocyclic anilide rings and their synthetic precursors, R-isomers, and non-hydroxylated and/or non-chiral propanamides, and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.