41873-65-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (2-hydroxyphenyl)acetate is used as a synthetic intermediate for the preparation of novel anti-inflammatory agents. Its chemical structure allows for the creation of new compounds that can potentially offer relief from inflammation and related conditions.
As a synthetic intermediate, ethyl (2-hydroxyphenyl)acetate is crucial in the development of new medications, particularly those aimed at treating inflammation. Its light yellow liquid form and unique chemical properties make it a valuable component in the pharmaceutical industry's ongoing efforts to create effective and innovative treatments for various health issues.

InChI:InChI=1/C10H12O3/c1-2-13-10(12)7-8-5-3-4-6-9(8)11/h3-6,11H,2,7H2,1H3

Upstream product

• 64-17-5 ethanol 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 101-97-3 Ethyl 2-phenylethanoate 
• 141-78-6 ethyl acetate 
• 90-02-8 salicylaldehyde 

Downstream Products

• 156005-36-6 [2-(3-Bromo-propoxy)-phenyl]-acetic acid ethyl ester 
• 186135-55-7 4-Ethoxy-2H,5H-1-benzoxepin-2-one 
• 875629-44-0 [2-(4-bromo-2-fluoro-benzyloxy)-phenyl]-acetic acid ethyl ester 
• 916908-22-0 [2-(4-fluoro-benzyloxy)-phenyl]-acetic acid ethyl ester 

Relevant academic research and scientific papers

Insights into Ruthenium(II/IV)-Catalyzed Distal C?H Oxygenation by Weak Coordination

C?H hydroxylation of aryl acetamides and alkyl phenylacetyl esters was accomplished via challenging distal weak O-coordination by versatile ruthenium(II/IV) catalysis. The ruthenium(II)-catalyzed C?H oxygenation of aryl acetamides proceeded through C?H ac

Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones

A phosphine-catalyzed domino process of benzofuranones with allenoates has been developed which furnishes highly functionalized unsymmetrical 3,3-disubstituted benzofuranones in synthetically useful yields. The mechanism for the transformation is a tandem β-umpolung/γ-umpolung process.

Structure-based lead optimization and biological evaluation of BAX direct activators as novel potential anticancer agents

The first direct activator of BAX, a pro-apoptotic member of the BCL-2 family, has been recently identified. Herein, a structure-based lead optimization turned out into a small series of analogues, where 8 is the most potent compound published so far. 8 was used as pharmacological tool to ascertain, for the first time, the anticancer potential of BAX direct activators and the obtained results would suggest that BAX direct activators are potential future anticancer drugs rather than venoms.

Transition-Metal-Free Synthesis of 2-Substituted Methyl Benzo[b]furan-3-carboxylates

A concise and highly efficient synthetic pathway was developed for 2-substituted methyl benzo[b]furan-3-carboxylates. This method provides convenient and cost-effective access for 2-substituted methyl benzo[b]furan-3-carboxylates without the use of a transition metal catalyst for synthesis. Furthermore, in most cases, this method gives excellent yields and conventional flash column chromatography is not needed for purification.

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

Design, synthesis, and antifungal activities of new β-methoxyacrylate analogues

Strobilurins have become one of the most important classes of agricultural fungicides. To search for new strobilurin derivatives with high activity against resistant pathogens, a series of new β-methoxyacrylate analogues containing substituted pyrimidine in the side chain with strobilurin pharmacophore were synthesized and their biological activities were tested. The compounds were confirmed and characterized by 1H-NMR, elemental analysis and mass spectroscopy. The bioassays indicated that most of the compounds 1 exhibited potent antifungal activities against Colletotrichum orbiculare, Botrytis cinerea Pers and Phytophthora capsici Leonian at a concentration of 50 μg mL-1. Notably, compound 1b (R = 2,5-dimethylphenyl) showed better antifungal activity against all the tested fungi than the commercial strobilurin fungicide azoxystrobin.

Synthesis of a 6H-chromeno[3,4-b]quinoline and a 6a,12a-dehydro-7-azarotenoid

The preparation of a 6H-chromeno[3,4-b]quinoline via a palladium-mediated coupling reaction, and the first synthesis of a nitrogenous dehydro-analogue of the naturally occurring rotenoids are reported.

Iron-catalyzed tandem oxidative coupling and annulation: An efficient approach to construct polysubstituted benzofurans

The combination of FeCl3·6H2O and di-tert-butyl peroxide offers a novel and efficient method for the construction of polysubstituted benzofurans 3 from the reaction of simple phenols 1 and β-keto esters 2, which are expected to give coumarins in the well-known Pechmann condensation. A variety of phenols reacted with β-keto esters to provide a range of benzofuran products in moderate to excellent yields. The regio-specific annulation was proven by the X-ray molecular structure of the product 3k. Hydrate of FeCl3 is essential for an achievement of the present transformation. The kinetic isotopic effect (KIE) experiments were carried out by competition experiments and displayed a kH/k D = 1.0 ± 0.1. The kinetic isotopic effect indicated that aromatic C-H bond cleavage is not involved in the rate-determining steps of the present transformation. Moreover, the results clearly demonstrate that the dichotomous catalytic behavior of the iron catalyst, which is transition-metal catalyst in the oxidative coupling step and Lewis acid in the condensation step. The possible intermediate 5 was synthesized and converted into the desired benzofuran 3a under the reaction conditions. A tentative mechanism of the formation of benzofurans 3 was proposed.

Synthesis, characterization and structure-activity relationship analysis of novel depsides as potential antibacterials

Twenty-six depsides were synthesized to screen for their antibacterial activity. All of them were reported for the first time. Their chemical structures were clearly determined by 1H NMR, 13C NMR, ESI mass spectra and elemental analyses, coupled with one selected single-crystal structure. All the compounds were assayed for antibacterial activities against three Gram-positive bacterial strains (Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6538 and Streptococcus faecalis ATCC 9790) and three Gram-negative bacterial strains (Escherichia coli ATCC 35218, Pseudomonas aeruginosa ATCC 13525 and Enterobacter cloacae ATCC 13047) by MTT method. Compound 2-(2-methoxy-2-oxoethyl)phenyl 3-nitrobenzoate (C10) and 2-(2-ethoxy-2-oxoethyl)phenyl 3-nitrobenzoate (C23) showed powerful antibacterial activities against B. subtilis with MIC of 0.78 μg/mL while compound 2-(2-methoxy-2-oxoethyl)phenyl 2-(3,4-diethoxyphenyl)acetate (C8) and 2-(2-ethoxy-2-oxoethyl)phenyl 2-(3,4-diethoxyphenyl)acetate (C21) exhibited significant antibacterial activities against E. coli with MIC of 1.562 μg/mL, which were superior to the positive controls penicillin G and kanamycin B, respectively. On the basis of the biological results, structure-activity relationships were discussed.

COMPOUNDS AND METHOD FOR REDUCING URIC ACID

Uric acid in mammalian subjects is reduced and excretion of uric acid is increased by administering a compound of Formula (I) or a pharmaceutically acceptable salt thereof. In Formula (I) m is 0, 1, 2, 3 or 4; n is 0 or 1; m + n is not more than 4; t is 0 or 1; q is 0 or 1; and r is 0, 1 or 2. R6 is hydrogen, methyl or ethyl and R12 is hydrogen or methyl, or R6 is hydroxy and R12 is hydrogen, or R6 is O and R12 is absent, or R6 and R12 together are -CH2CH2-. R7 is hydrogen or alkyl having from 1 to 3 carbon atoms. One of R8 and R9 is alkyl having from 1 to 3 carbon atoms, and the other is hydrogen or alkyl having from 1 to 3 carbon atoms. R10 is hydrogen, halo, alkyl having from 1 to 3 carbon atoms or alkoxy having from 1 to 3 carbon atoms. X is C(O) and r is 0 and t is 0; or X is NH(R11) wherein R11 is hydrogen or alkyl having from 1 to 3 carbon atoms. A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from halo, hydroxy, methyl, ethyl, perfluoromethyl, methoxy, ethoxy, and perfluoromethoxy; or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of Formula (I) by a ring carbon; or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently monosubstituted by methyl or ethyl. The uric acid-lowering effects of the Compounds of Formula (I) are used to treat or prevent a variety of conditions including gout, hyperuricemia, elevated levels of uric acid that do not meet the levels customarily justifying a diagnosis of hyperuricemia, renal dysfunction, kidney stones, cardiovascular disease, risk for developing cardiovascular disease, tumor-lysis syndrome, and cognitive impairment.