59490-33-4

Usage

Derivative of propanoic acid

It is a modified version of the propanoic acid molecule This means that the compound is derived from or related to propanoic acid, which is a simple carboxylic acid.

Contains a benzene ring

The structure of the compound includes a benzene ring A benzene ring is a six-carbon ring with alternating single and double bonds, which is a fundamental structure in many organic compounds.

Chloro and phenyl group attached

The compound has a chloro (Cl) and a phenyl group (a group containing a benzene ring) attached to the benzene ring These functional groups are responsible for the compound's chemical properties and reactivity.

Potential pharmaceutical properties

The compound has possible applications in the pharmaceutical industry This means that it may have properties that make it useful in the development of drugs or medications.

Used in the synthesis of various drugs

It serves as a building block or intermediate in the creation of different pharmaceutical compounds This indicates that the compound is an important component in the production of other drugs.

Anti-inflammatory and analgesic effects

The compound is known for reducing inflammation and relieving pain These are some of the therapeutic effects that the compound may have, making it a potential candidate for pain-relief medications.

Candidate for pain-relief medications

It is being considered for the development of drugs that alleviate pain This highlights the compound's potential use in creating new medications for pain management.

Studied for potential application in treating various health conditions

Researchers are exploring its possible uses in addressing other medical issues This suggests that the compound may have additional therapeutic effects beyond its known anti-inflammatory and analgesic properties.

InChI:InChI=1/C16H14ClNO3/c17-13-8-6-12(7-9-13)15(19)18-14(16(20)21)10-11-4-2-1-3-5-11/h1-9,14H,10H2,(H,18,19)(H,20,21)/p-1/t14-/m1/s1

Upstream product

• 150-30-1 Phenylalanine 
• 122-01-0 4-chloro-benzoyl chloride 
• 74-11-3 para-chlorobenzoic acid 
• 59490-38-9 N-(p-chlorobenzoyl)phenylalanine methyl ester 
• 63-91-2 L-phenylalanine 

Downstream Products

• 934220-95-8 N-(N-(4-chloro-benzoyl)-L-phenylalanyl)-L-phenylalaninol 
• 59490-38-9 N-(p-chlorobenzoyl)phenylalanine methyl ester 
• 22887-59-8 2-Benzyl-2-(p-chlor-benzamido)-3-dimethylamino-propionsaeure 
• 138111-76-9 D,L-N-(3-Methoxy propyl)-N-pentyl-2-(4-chlorobenzoyl amino)-3-phenyl-propionamide 
• 22887-55-4 4-benzyl-2-(4-chloro-phenyl)-4H-oxazol-5-one 
• 71456-32-1 4-[[2-(4-Chloro-benzoylamino)-3-phenyl-propionyl]-(4-methoxy-phenyl)-amino]-butyric acid 
• 1367346-95-9 (S)-4-benzyl-2-(4-chlorophenyl)oxazol-5(4H)-one 
• 1367347-01-0 (S)-4-allyl-4-benzyl-2-(4-chlorophenyl)oxazol-5(4H)-one 

Relevant academic research and scientific papers

Hybrids of aurantiamide acetate and isopropylated genipin as potential anti-inflammatory agents: The design, synthesis, and biological evaluation

A novel series of hybrids designed on the basis of aurantiamide acetate and isopropylated genipin were synthesized and biologically evaluated as anti-inflammatory agents. Among them, compound 7o exhibited the best inhibitory activity against TNF-α secretion (IC50?=?16.90?μM) and was selected for further in vitro and in vivo functional study. The results demonstrated that 7o was capable of suppressing the expression of LPS-induced iNOS and COX-2, as well as reducing the production of NO at the concentration of 5?μM, which may be resulted from its regulation of NF-κB signaling and MAPK signaling. Moreover, compound 7o exhibited favorable in vivo anti-inflammatory activity with an inhibition rate of 53.32% against xylene-induced ear swelling in mice at the dose of 5?mg/kg.

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation

A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with nonconjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction, and a cleavable bidentate directing group appended to the alkene to control the regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal reaction conditions to afford products bearing α,α-disubstituted α-amino-acid derivatives with high yields and high enantioselectivity.

Enantioselective synthesis of pyrano[2,3-: C] pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

An enantioselective [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones has been successfully developed through a squaramide catalysis strategy. This protocol provides an efficient and mild access to obtain pyrano[2,3-c]pyrrole scaffolds containing contiguous quaternary and tertiary stereogenic centers in excellent yields (up to 99%) with high levels of diastereo- and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the observed stereoselectivity.

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Optimization Strategy of Novel Peptide-Based Michael Acceptors for the Treatment of Human African Trypanosomiasis

This paper describes an optimization strategy of the highly active vinyl ketone 3 which was recognized as a strong inhibitor of rhodesain of Trypanosoma brucei rhodesiense, endowed with a ksecond value of 67 × 106 M-1 min

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols

A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.

Bronsted acid accelerated Pd-catalyzed direct asymmetric allylic alkylation of azlactones with simple allylic alcohols: A practical access to quaternary allylic amino acid derivatives

A Bronsted acid accelerated Pd-catalyzed asymmetric allylic alkylation of azlactones with simple allylic alcohols under mild reaction conditions has been realized, which provides a direct and readily scalable approach for the synthesis of all-carbon quaternary allylic amino acid derivatives in excellent yields and good enantioselectivities. (Chemical Equation Presented).

Organocatalyzed asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones: Synthesis of α,α-disubstituted α-amino acid derivatives

The first asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones catalyzed by cinchona alkaloid derived bifunctional thiourea catalysts was developed. A series of α,α-disubstituted α-amino acid derivatives bearing a quaternary stereocenter at the α-position were obtained in high yields with excellent diastereo- and enantioselectivities (up to -20:1 dr and 99% ee). In addition, the trichloromethyl moiety in these adducts was identified as a good leaving group.