111479-08-4

Upstream product

• 150-76-5 4-methoxy-phenol 
• 535-11-5 Ethyl 2-bromopropionate 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 6111-99-5 ethyl diazoalaninate 
• 13794-15-5 2-(4-methoxyphenoxy)propanoic acid 
• 1877-75-4 2-(4-methoxyphenoxy)acetic acid 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 

Downstream Products

• 1877-75-4 2-(4-methoxyphenoxy)acetic acid 
• 17509-54-5 α-(4-methoxyphenoxy)-2-methylpropionic acid 
• 150-76-5 4-methoxy-phenol 
• 106-51-4 p-benzoquinone 
• 401791-15-9 2-(4-Methoxyphenoxy)-3-(4-benzyloxyphenyl)-2-methylpropionic Acid Ethyl Ester 
• 1434516-80-9 2-(4-methoxyphenoxy)-N-(2-(pyridine-4-yl)benzo[d]oxazol-5-yl)propanamide 
• 13794-15-5 2-(4-methoxyphenoxy)propanoic acid 

Relevant academic research and scientific papers

Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds

The catalytic insertion of copper carbenoids into O-H bonds affords synthetically useful α-alkyl/aryl-α-alkoxy/aryloxy derivatives. Herein, the design, preparation and application of supramolecularly regulated copper(i) complexes of bisoxazoline ligands is reported. We have demonstrated that the catalytic performance of these systems can be modulated by the use of an external molecule (i.e.the regulation agent), which interacts with a polyethyleneoxy chain on the ligand (i.e.the regulation site)viasupramolecular interactions. This approach has been applied to an array of structurally diverse alcohols (cycloalkyl, alkyl and aryl derivatives). Moreover, we have used this methodology to synthesise advanced synthetic intermediates of biologically relevant compounds.

Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.

Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.

Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists

Compounds represented by the following structural formula (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: n is 2, 3, or 4 and W is CH2, CH(OH), C(O) or O; R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl, aryl-alkyl, heteroaryl-alkyl, cycloalkyl-alkyl, or t-butyl; R2 is H, alkyl, haloalkyl or phenyl; Y is an unsubstituted or substituted thiophen-2,5-diyl or phenylene; R3 is alkyl or haloalkyl; R4 is a substituted or unsubstituted phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, quinolyl, pyridyl or benzo[1,3]dioxol-5-yl group; and R5 is H, alkyl, or aminoalkyl; are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.

Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation

A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.

Electrochemically-induced spirolactonization of α-(methoxyphenoxy)alkanoic acids into quinone ketals

Anodic oxidation of two series of α-(2)- and α-(4-methoxyphenoxy)alkanoic acids were studied both at the analytical and preparative scales in order to delineate mechanistic aspects of electrochemically induced spirolactonization and to develop synthetically useful orthoquinone bis- and monoketals. Although α-monomethylated carboxylic acids and acetic acid derivatives do not undergo any spiroannulation, α-dimethylated carboxylic acids furnished spirolactones in high yields. A gem-dimethyl effect is invoked to explain these differences in cyclization capacity. Electrooxidation conditions can be selected to furnish either quinone spirolactone bis- or monoketals. Chemoselective monohydrolysis of bisketals can also be accomplished in a stepwise fashion to furnish the corresponding spirolactone monoketals, but the ortho compound unfortunately dimerized in situ via a Diels-Alder process. An ECEC pathway is proposed to rationalize the observed spirolactonizations on the basis of cyclic voltammetry analyses.

Kinetics and mechanism of thermal gas-phase elimination of α-substituted carboxylic acids: Role of relative basicity of α-substituents and acidity of incipient proton

2-Phenoxypropanoic acid together with five of its aryl derivatives, its phenylthio and its N-phenylamino analogues were pyrolyzed at 494-566 K. The reactions were homogeneous, polar and free from catalytic and radical pathways, and obeyed a first-order rate equation. The limits of the Arrhenius log A (s-1) and E (kJ mol-1) values obtained for these reactions averaged 11.98 ± 1.71 and 158.1 ± 17.4, respectively. Analysis of the pyrolysates showed the elimination products to be carbon monoxide, acetaldehyde and the corresponding phenol, thiophenol or aniline compounds. The pyrolysis of 2-phenoxy- and 2-(N-phenylamino)-1-propanol was also investigated over the temperature range 638-792 K. The kinetic results and products analysis lend support to a reaction pathway involving a five-membered cyclic polar transition state. Copyright

[(Isopropylideneamino)oxy]-ethyl-2-[[6-chloroquinoxalinyl)oxy]phenoxy]propionate postemergent herbicide

The oxime ester compound [(isopropylideneamino)oxy]-ethyl-2-[[(6-chloroquinoxalinyl)oxy]phenoxy]propionate, processes for the preparation thereof, herbicidal compositions containing said compound and methods of use of the composition.