39718-97-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-(4-aminophenyl)propionate serves as a crucial precursor in the synthesis of various drugs, particularly analgesics and anti-inflammatory medications. Its unique structure allows for the development of potent therapeutic agents that can alleviate pain and reduce inflammation.
Used in Research and Development Labs:
In research and development labs, methyl 2-(4-aminophenyl)propionate is utilized as a building block in the creation of new therapeutic compounds. Its versatile nature enables scientists to explore its potential in designing innovative drugs and treatments for various medical conditions.
Used in Organic Synthesis:
Methyl 2-(4-aminophenyl)propionate is considered an important intermediate in organic synthesis due to its wide range of applications. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules and advanced materials.

InChI:InChI=1/C10H13NO2/c1-7(10(12)13-2)8-3-5-9(11)6-4-8/h3-7H,11H2,1-2H3

Upstream product

• 50415-69-5 methyl 2-(4-nitrobenzene)propionate 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 106-47-8 4-chloro-aniline 
• 19910-33-9 2-(4-nitrophenyl)propanoic acid 
• 28042-27-5 α-Methylene-4-nitrobenzeneacetic acid methyl ester 
• 67-56-1 methanol 
• 2945-08-6 methyl (4-nitrophenyl)acetate 
• 104-03-0 4-nitrobenzeneacetic acid 
• 100-00-5 4-chlorobenzonitrile 
• 61881-49-0 Diethyl 2-methyl-2-(4-nitrophenyl)malonate 

Downstream Products

• 109226-98-4 methyl 4-<2H-1,4-benzoxazin-3-yl>amino-α-methylphenylacetate 
• 102038-11-9 methyl 4-isothiocyanatophenyl-α-methyl acetate 
• 93371-95-0 metile 2-<4-(3-oxo-1,2-benzisotiazolin-2-il)fenil>propionato 
• 109226-99-5 methyl 4-<6-nitro-2H-1,4-benzoxazin-3-yl>amino-α-methylphenylacetate 
• 109227-02-3 methyl 4-<7-nitro-2H-1,4-benzoxazin-3-yl>amino-α-methylphenylacetate 
• 109227-01-2 methyl 4-<2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-3-yl>amino-α-methylphenylacetate 
• 65784-33-0 methyl 2-(4-hydroxyphenyl)propanoate 
• 83528-18-1 2-[4-(Pyridin-2-ylamino)-phenyl]-propionic acid methyl ester 
• 874962-83-1 1-[4-(2-methoxy-1-methyl-2-oxoethyl)phenyl]-5-oxoproline 
• 852068-70-3 2-[4-(3-chloro-propane-1-sulfonylamino)-phenyl]-propionic acid methyl ester 
• 852068-62-3 methyl 2-[4-(2,4-dioxoimidazolidin-1-yl)phenyl]propanoate 

Relevant academic research and scientific papers

Structural optimization and in vitro profiling of N-phenylbenzamide-based farnesoid X receptor antagonists

Activation of the nuclear farnesoid X receptor (FXR) which acts as cellular bile acid sensor has been validated as therapeutic strategy to counter liver disorders such as non-alcoholic steatohepatitis by the clinical efficacy of obeticholic acid. FXR antagonism, in contrast, is less well studied and potent small molecule FXR antagonists are rare. Here we report the systematic optimization of a novel class of FXR antagonists towards low nanomolar potency. The most optimized compound antagonizes baseline and agonist induced FXR activity in a full length FXR reporter gene assay and represses intrinsic expression of FXR regulated genes in hepatoma cells. With this activity and a favorable toxicity-, stability- and selectivity-profile it appears suitable to further study FXR antagonism in vitro and in vivo.

Photochemical intramolecular amination for the synthesis of heterocycles

Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.

Novel propanamides as fatty acid amide hydrolase inhibitors

Fatty acid amide hydrolase (FAAH) has a key role in the control of the cannabinoid signaling, through the hydrolysis of the endocannabinoids anandamide and in some tissues 2-arachidonoylglycerol. FAAH inhibition represents a promising strategy to activate the cannabinoid system, since it does not result in the psychotropic and peripheral side effects characterizing the agonists of the cannabinoid receptors. Here we present the discovery of a novel class of profen derivatives, the N-(heteroaryl)-2-(4-((2-(trifluoromethyl)pyridin-4-yl)amino)phenyl)propanamides, as FAAH inhibitors. Enzymatic assays showed potencies toward FAAH ranging from nanomolar to micromolar range, and the most compounds lack activity toward the two isoforms of cyclooxygenase. Extensive structure-activity studies and the definition of the binding mode for the lead compound of the series are also presented. Kinetic assays in rat and mouse FAAH on selected compounds of the series demonstrated that slight modifications of the chemical structure could influence the binding mode and give rise to competitive (TPA1) or non-competitive (TPA14) inhibition modes.

Potent multitarget FAAH-COX inhibitors: Design and structure-activity relationship studies

Non-steroidal anti-inflammatory drugs (NSAIDs) exert their pharmacological effects by inhibiting cyclooxygenase (COX)-1 and COX-2. Though widely prescribed for pain and inflammation, these agents have limited utility in chronic diseases due to serious mechanism-based adverse events such as gastrointestinal damage. Concomitant blockade of fatty acid amide hydrolase (FAAH) enhances the therapeutic effects of the NSAIDs while attenuating their propensity to cause gastrointestinal injury. This favorable interaction is attributed to the accumulation of protective FAAH substrates, such as the endocannabinoid anandamide, and suggests that agents simultaneously targeting COX and FAAH might provide an innovative strategy to combat pain and inflammation with reduced side effects. Here, we describe the rational design and structure-active relationship (SAR) properties of the first class of potent multitarget FAAH-COX inhibitors. A focused SAR exploration around the prototype 10r (ARN2508) led to the identification of achiral (18b) as well as racemic (29a-c and 29e) analogs. Absolute configurational assignment and pharmacological evaluation of single enantiomers of 10r are also presented. (S)-(+)-10r is the first highly potent and selective chiral inhibitor of FAAH-COX with marked in vivo activity, and represents a promising lead to discover novel analgesics and anti-inflammatory drugs.

Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.

2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them

The present invention relates to (R,S) 2-aryl-propionic acids and derivatives, their single enantiomer (S) and to pharmaceutical compositions containing them, which are used in the prevention and treatment of tissue damage due to the exacerbated recruitment of polymorphonucleated neutrophils (PMN leukocytes) at inflammation sites. The present invention provides compounds for use in the treatment of transient cerebral ischemia, bullous pcmphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and damages caused by ischemia and reperfusion.

Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2

Chemokines CXCL8 and CXCL1 play a key role in the recruitment of neutrophils at the site of inflammation. CXCL8 binds two membrane receptors, CXCR1 and CXCR2, whereas CXCL1 is a selective agonist for CXCR2. In the past decade, the physiopathological role of CXCL8 and CXCL1 has been investigated. A novel class of small molecular weight allosteric CXCR1 inhibitors was identified, and reparixin, the first drug candidate, is currently under clinical investigation in the prevention of ischemia/reperfusion injury in organ transplantation. Reparixin binding mode to CXCR1 has been studied and used for a computer-assisted design program of dual allosteric CXCR1 and CXCR2 inhibitors. In this paper, the results of modeling-driven SAR studies for the identification of potent dual inhibitors are discussed, and three new compounds (56, 67, and 79) sharing a common triflate moiety have been selected as potential leads with optimized pharmacokinetic characteristics.

DITHIAZOLE COMPOUNDS, MATRIX METALLOPROTEASE INHIBITORS AND EXTERNAL PREPARATIONS FOR THE SKIN

A dithiazole compound or a salt thereof expressed by formula (I): wherein R1, is hydrogen atom, alkyl, etc.; R2 is hydrogen atom, hydroxy, alkyl, aryl, arylalkoxy, arylalkyl, etc.; R3 is one group of formulae (II), (III) and (IV): This compound has an excellent inhibiting action on matrix metalloprotease (MMPs) activity, and is useful for pharmaceutical, cosmetic and skin external compositions.

A novel α-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations

4-Aminophenyl cations (expediently generated by photolysis of 4-chloroaniline and its N,N-dimethyl derivative by photolysis in MeCN) added to enamines and gave the corresponding α-(4-aminophenyl) ketones in satisfactory yields. The yields of the same ketones were increased when silyl enol ethers were used in the place of enamines. The α-arylation of silyl enol ethers of aldehydes occurred with lower yields and only with the N,N-dimethyl derivative. The procedure was successful with ketene silyl acetals giving in a single step a good yield of α-(4-aminophenyl)propionic(acetic) esters, known intermediates for the preparation of analgesic compounds. The reaction of the aryl cation with Danishefsky's diene gave the arylated β-methoxy enone. The method is complementary to the recently developed palladium-catalyzed α-arylation and occurs under neutral conditions.

Quinazoline derivatives possessing anti-tumor activity

The invention relates to quinazoline derivatives, or pharmaceutically-acceptable salts thereof, which possess anti-tumor activity; to processes for their manufacture; and to pharmaceutical compositions containing them. The invention provides a quinazoline of the formula: STR1 wherein R1 is hydrogen or amino, or alkyl or alkoxy each of up to 6 carbon atoms; or R1 is substituted alkyl or alkoxy each of up to 3 carbon atoms; R2 is hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, halogenoalkyl or cyanoalkyl each of up to 6 carbon atoms; Ar is phenylene or heterocyclene; L is a group of the formula --CO.NH--, --NH.CO--, --CO.NR3 --, --NR3. CO--, --CH=CH--, --CH2 O--, --OCH2, --CH2 S--, --SCH2 --, --CO.CH2 --, --CH2.CO-- or --CO.O--, wherein R3 is alkyl of up to 6 carbon atoms; and Y is aryl or heteroaryl or a hydrogenated derivative thereof: or Y is a group of the formula --A--Y1 in which A is alkylene, cycloalkylene, alkenylene or alkynylene each of up to 6 carbon atoms and Y1 is aryl or heteroaryl or a hydrogenated derivative thereof; or a pharmaceutically-acceptable salt thereof.