6280-80-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Formylphenoxyacetic acid is used as a synthetic intermediate for the development of azomethine derivatives, which are known for their diverse biological activities, including potential applications in the treatment of various diseases and disorders. The synthesis of these derivatives is crucial for expanding the range of available pharmaceuticals and improving patient outcomes.
Used in Chemical Industry:
In the chemical industry, 2-Formylphenoxyacetic acid is utilized in the preparation of specific ligands, such as L(1)H(2) and L(2)H(2). These ligands are essential components in various chemical processes and reactions, often playing a critical role in enhancing the efficiency and selectivity of these processes. The use of 2-Formylphenoxyacetic acid in ligand synthesis contributes to the advancement of chemical research and the development of new materials and products.
Overall, 2-Formylphenoxyacetic acid is a valuable compound with applications in both the pharmaceutical and chemical industries, showcasing its importance in the synthesis of various organic compounds and the development of new products and therapies.

InChI:InChI=1/C9H8O4/c10-5-7-3-1-2-4-8(7)13-6-9(11)12/h1-5H,6H2,(H,11,12)/p-1

Upstream product

• 41873-61-4 ethyl (2-formylphenoxy)acetate 
• 91143-61-2 3-oxo-2-phenoxy-propionic acid ethyl ester 
• 90-02-8 salicylaldehyde 
• 79-11-8 chloroacetic acid 
• 40359-34-0 methyl o-formylphenoxyacetate 
• 3926-62-3 sodium monochloroacetic acid 
• 89-95-2 2-methyl-benzyl alcohol 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 40359-34-0 methyl o-formylphenoxyacetate 
• 13410-86-1 [2-(isonicotinoylhydrazono-methyl)-phenoxy]-acetic acid 
• 102659-67-6 3-(2-methyl-indol-3-yl)-propionic acid-(2-carboxymethoxy-benzylidenehydrazide) 
• 271-89-6 1-benzofurane 
• 6965-69-1 2-(2-formyl-4-nitrophenoxy)acetic acid 
• 24589-89-7 2-(4-bromo-2-formylphenoxy)acetic acid 
• 22043-09-0 (2-thiosemicarbazonomethyl-phenoxy)-acetic acid 
• 3179-14-4 [2-((E)-2-Nitro-vinyl)-phenoxy]-acetic acid 
• 41873-61-4 ethyl (2-formylphenoxy)acetate 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 635-53-0 (2-carboxyphenoxy)acetic acid 
• 75270-15-4 (2-Formyl-phenoxy)-acetyl chloride 
• 126861-88-9 (E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetic acid 

Relevant academic research and scientific papers

One-dimensional Europium-coordination polymer as luminescent sensor for highly selective and sensitive detection of 2,4,6-trinitrophenol

Three isostructural lanthanide coordination polymers (LnCPs), [Ln(L)6(DMF)]n {HL = 2-(2-formylphenoxy) acetic acid, Ln = Sm (1); Eu (2); Tb (3)} have been synthesized by solvothermal reaction and characterized. Single crystal analyse

HEMIAMINAL-TAG FOR PROTEIN LABELING AND PURIFICATION

The invention pertains to the synthesis, isolation, and characterization of hemiaminal for selective labeling of peptides, proteins, antibodies, and organic fragments with -C(=0) CH2NH2 and derivatives with -CH2NH2 group over -C(=0) CHRNH2 group (where R≠H). The invention also pertains to the method of single-site immobilization of proteins through N-terminus Gly on solid phase. The invention includes late-stage tagging of N-terminus Gly with an affinity tag, 19F NMR probe, and a fluorophore and a method for metal-free protein purification and isolation of analytically pure proteins.

Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr2NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

Design, synthesis, and biological evaluation of thiazolidine-2,4-dione conjugates as PPAR-γ agonists

A library of synthesized conjugates of phenoxy acetic acid and thiazolidinedione 5a-m showed potent peroxisome proliferator activated receptor-γ (PPAR-γ) transactivation as well as significant blood glucose lowering effect comparable to the standard drugs pioglitazone and rosiglitazone. Most of the compounds showed higher docking scores than the standard drug rosiglitazone in the molecular docking study. Compounds 5l and 5m exhibited PPAR-γ transactivation of 54.21 and 55.41%, respectively, in comparison to the standard drugs pioglitazone and rosiglitazone, which showed 65.94 and 82.21% activation, respectively. Compounds 5l and 5m significantly lowered the blood glucose level of STZ-induced diabetic rats. Compounds 5l and 5m lowered the AST, ALT, and ALP levels more than the standard drug pioglitazone. PPAR-γ gene expression was significantly increased by compound 5m (2.00-fold) in comparison to the standard drugs pioglitazone (1.5-fold) and rosiglitazone (1.0-fold). Compounds 5l and 5m did not cause any damage to the liver and could be considered as promising candidates for the development of new antidiabetic agents.

A new fluorescent pH probe for imaging lysosomes in living cells

A new rhodamine B-based pH fluorescent probe has been synthesized and characterized. The probe responds to acidic pH with short response time, high selectivity and sensitivity, and exhibits a more than 20-fold increase in fluorescence intensity within the pH range of 7.5-4.1 with the pKa value of 5.72, which is valuable to study acidic organelles in living cells. Also, it has been successfully applied to HeLa cells, for its low cytotoxicity, brilliant photostability, good membrane permeability and no 'alkalizing effect' on lysosomes. The results demonstrate that this probe is a lysosome-specific probe, which can selectively stain lysosomes and monitor lysosomal pH changes in living cells.

In situ Bronsted-Lowry acid catalyzed syntheses, characterization, single crystal XRD, electronic spectral-, DPPH radical scavenging-, and DNA protection studies of aryl-3,3′-bis(indolyl)methanes

A series of novel aryl-3,3′-bis(indolyl)methanes (BIMs) were synthesized using indole and formylphenoxyaliphatic acid(s) in water in the absence of any catalyst. The formylphenoxyaliphatic acid behaves as an in situ Bronsted-Lowry acid catalyst in water. UV-Visible and fluorescence spectra of the compounds were recorded in selected solvents. The gas phase geometry optimization of the compounds were achieved using DFT calculations at B3LYP/3-21G(*) level of theory. The electronic properties, such as HOMO-LUMO energies were calculated using the above method based on the optimized structure. Compounds have better DPPH radical scavenging activity and reduction of oxidative damage of DNA.

POLYMORPHIC FORM OF 5-(4-[4-(5-CYANO-1H-INDOL-3-YL) BUTYL] PIPERAZIN-1-YL) BENZOFURAN-2-CARBOXAMIDE AND PROCESS FOR PREPARING THEREOF

The present invention provides a solid state Form-Z of 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide. The present invention also provides a process for preparing Form-Z of 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide comprising the steps of i) reacting solid state form of 5-(1-piperazinyl)benzofuran-2-carboxamide or its salts with 3-(4-chlorobutyl)-1H-indole-5-carbonitrile an organic solvent in presence of a base to obtain crude vilazodone free base; ii) purifying the crude vilazodone free base of step (i) in an organic solvent; iii) treating the purified vilazodone free base of step (ii) with an organic solvent to obtain solid state form-Z of vilazodone. The present invention further provides a pharmaceutical composition comprising a therapeutically effective amount of an amorphous form of vilazodone hydrochloride and use of solid state Form-Z of vilazodone for the treatment of major depressive disorders.

An efficient one pot syntheses of aryl-3,3′-bis(indolyl)methanes and studies on their spectral characteristics, DPPH radical scavenging-, antimicrobial-, cytotoxicity-, and antituberculosis activity

An efficient one-pot syntheses of aryl-3,3′-bis(indolyl)methanes (BIMs) from indole/2-methylindole and formylphenoxyaliphatic acid(s) is described. Esterification of carboxylic acid and aromatic electrophilic substitution reactions are achieved simultaneous in the presence of potash alum as a catalyst. This catalyst could be recovered and reused without substantial loss in its catalytic activity and the methodology could be applied on a range of closely related substrates. The solvation characteristics in ground and excited states of the compounds by monitoring the absorbance and fluorescence band maxima have been studied. The fluorescence studies in protic and aprotic solvents were rationalized on the basis of solute-solvent interaction and substituents effect on these photophysical processes analyzed. The compounds prepared showed efficient antimicrobial effect against human pathogens, cytotoxicity against A431 cell line, and DPPH radical scavenging effect. Single crystal XRD studies have been carried out for a few compounds synthesized in this work.

POLYMORPHIC FORM OF 5-(4-[4-(5-CYANO-1H-INDOL-3- YL)BUTYL]PIPERAZIN-1-YL) BENZOFURAN-2-CARBOXAMIDE

The present invention relates to a process for the preparation of 5-(4-[4-(5- cyano- 1 H-indol-3 -yl)butyl] piperazin- 1 -yl)benzofuran-2-carboxamide of Formula (1) or its pharmaceutically acceptable salt, solvates or hydrates thereof. In particular, the present invention provides a novel intermediate compound, 5-(4-substitutedpiperazin- 1-yl)benzofuran-2-carboxamide of Formula (X). The present invention further provides solid state form of 5-(4-[4-(5-cyano-1H-indol-3- yl) butyl]piperazin-1-yl)benzofuran-2-carboxamide of Formula (1) and process for its preparation.

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-γ/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r2 = 0.989 and a good cross validated value, q 2 = 0.583.