60460-30-2

Usage

InChI:InChI=1/C8H11NO3/c1-2-7(10)9-5-3-4-6(9)8(11)12/h2,6H,1,3-5H2,(H,11,12)

Upstream product

• 814-68-6 acryloyl chloride 
• 147-85-3 L-proline 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 62571-86-2 captopril 
• 613256-52-3 β-hydroxy-α-methyl-N-acryloyl-(S)-proline 

Relevant academic research and scientific papers

A synthesis of captopril through a Baylis-Hillman reaction

A synthesis of the antihipertensive amide 1, named captopril, is described. The strategy is based on a Baylis-Hillman reaction between N-acryloylproline and formaldehyde. Subsequential diaster eoselective hydrogenation step and functional group interconversion provided captopril in good overall yield.

A shortened, protecting group free, synthesis of the anti-wrinkle venom analogue Syn-Ake exploiting an optimized Hofmann-type rearrangement

An unusual five-step synthesis of H-β-Ala-Pro-DabNHBz diacetate (a muscular nicotinic acetylcholine receptor antagonist) has been delineated through Hofmann-type rearrangement as a final step to build the target skeleton. The synthesis has been carried out using a protecting group free strategy and employed readily available reagents as the starting materials.

A DRUG AND SYNTHESIS OF THE DRUG TO TREAT HIGH BLOOD PRESSURE AND TYPE 2 DIABETES MELLITUS DISEASE

The invention relates to a drug and its method of manufacture, which allows to reduce hypertension and treat type 2 diabetes mellitus by using the drug as a dipeptidyl peptidase-4 (DPP-4) inhibitor. The rate of hypoglycemia of the drug in question is low and provides glycemic control and weight loss. The method of manufacturing the mentioned drug includes practical steps to convert the carboxyl group from captopril (1) to the nitrile group.

Optical active compound and synthesis and application method

The present invention provides an optically active N-(S)-((N-(R)-1-benzeneacetamide)-pyrrolidine)-acrylamide and a synthetic method and an application method thereof. The synthetic method is as below: step 1, reacting raw materials of (S)-proline and acryloyl chloride under basic conditions to prepare an intermediate (S)-1-acryloylpyrrolidine-2-carboxylic acid; step 2, reacting the intermediate (S)-1-acryloylpyrrolidine-2-carboxylic acid with R-(+)-alpha-methylbenzylamine under basic reaction conditions for preparing the target product N-(S)-((N-(R)-1-benzeneacetamide)-pyrrolidine)-acrylamide. The optically active N-(S)-((N-(R)-1-benzeneacetamide)-pyrrolidine)-acrylamide derivative can be used as an anion recognition receptor. The synthetic method of optically active N-(S)-((N-(R)-1-benzeneacetamide)-pyrrolidine)-acrylamide has the characteristics of mild reaction conditions, simple operation, few byproducts, easy purification; and the optically active polyacrylamide derivative has good performance anion recognition property.

Poly(n-acryl amino acids): A new class of biologically active polyanions

Poly(N-acryl amino acids) bearing side groups with a lipophilic character or having charged functional groups (i.e. -NH2, -COOH, -SH, -OH, and phenols) were synthesized from the radical polymerization of N-acryl amino acid monomers. Monomers were prepared from the reaction of acryloyl chloride and amino acid esters in dry solvents. Polymers of a broad molecular weight ranging from 3 000 to 60 000 Da were obtained. The polymers were optically active, and their structures were confirmed by 1H NMR and IR spectra and elemental analysis. Hydroxyl-containing polymers were sulfated in high conversion yields by SO3/pyridine complex. The newly synthesized linear homopolyanions were tested for heparin-like activities: (i) inhibition of heparanase enzyme, (ii) release of basic fibroblast growth factor (bFGF) from the extracellular matrix (ECM), and (iii) inhibition of smooth muscle cell (SMC) proliferation. Polymers based on tyrosine and leucine were highly active in all three tests (microgram level). Polymers based on phenylalanine, tert-leucine, and proline were active as heparanase inhibitors and FGF release, and polymers of trans-hydroxyproline, glycine, and serine were active only as heparanase inhibitors. The polymer of cis-hydroxyproline was inactive. It was found that a net anionic charge (i.e. carboxylic acid) is essential for biological activity. Thus, methyl ester derivatives of the active polymers, zwitterionic amino acid pendent groups (lysine, histidine), and decarboxylated amino acids (tyramine, ethanolamine) were inactive. The above active polymers did not exhibit anticoagulation activity which is considered the main limitation of heparin and heparinomimetics for clinical use. These synthetic poly(N-acryl amino acids) may have potential use in the inhibition of heparanase-mediated degradation of basement membranes associated with tumor metastasis, inflammation, and autoimmunity.

Models for Use of α-Amino Acids as Chiral Auxiliaries in Asymmetric Diels-Alder Reactions

Three different models, depending on the Lewis acid used as a catalyst and the α-amino acid used as a chiral auxiliary, account for the diastereofacial selectivity obtained in reactions of cyclopentadiene with N-acryloyl derivatives of L-proline, L-phenylalanine, L-alanine, and N-methyl-L-alanine esters.For α-amino acids without an NH group and aluminum catalysts, a reactive conformer with antiplanar enoate conformation similar to those postulated for acrylates with only one center capable of coordination is proposed.These dienophiles form a chelate complex, where the acryloyl moiety is in syn conformation, with TiCl4.For α-amino acids with an NH group, a reactive intermediate with an antiplanar disposition in the acryloyl moiety and the conformation of the amino ester fixed by an intramolecular hydrogen bond accounts for the results with both kinds of catalyst.These models seem to have general application for the use of α-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions.

Selenium containing derivatives of proline and pipecolic acid

New selenium containing derivatives of proline and pipecolic acid which have the general formula STR1 are useful as hypotensive agents.