2491-39-6

Usage

Uses

Used in Coordination Chemistry:
2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE is used as a chelating agent for its ability to bind with metal ions, facilitating the formation of stable metal complexes. This property is crucial in the study and application of coordination compounds.
Used in Synthesis of Metal Complexes:
In the synthesis of metal complexes, 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE serves as a ligand, contributing to the structural and functional diversity of the resulting complexes, which can have applications in various fields such as catalysis, materials science, and pharmaceuticals.
Used in Pharmaceutical Development:
2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE is used as a potential candidate for new drug development due to its pharmacological properties, including antioxidant and anti-inflammatory effects, which could be beneficial in treating a range of diseases and conditions.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE has been investigated for its potential applications, possibly due to its ability to interact with various chemical species and facilitate the detection or measurement of analytes.
Used as a Catalyst in Organic Synthesis:
2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE is utilized as a catalyst to accelerate organic reactions, improving the efficiency and selectivity of synthetic processes, which is valuable in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C8H7BrO3/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3,10-11H,4H2

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 108-46-3 recorcinol 
• 598-21-0 2-Bromoacetyl bromide 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 797813-79-7 4-(2-(4-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1173282-19-3 4-(2-(2-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1173282-17-1 4-(2-(3-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 924173-79-5 4-(2-(phenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1394893-17-4 4-(2-(biphenyl-4-yl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1414626-98-4 4-(2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1414627-32-9 4-(2-(2-chloro-5-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1556096-88-8 4, 4′-(4-nitrobenzylidene)-bis-[3-(2′,4′-dihyroxybenzoyl)-1H-2-benzopyran-1-one] 
• 1556096-89-9 4, 4'-(4-hydroxybenzylidene)-bis-[3-(2',4'-dihydroxybenzoyl)-1H-2-benzopyran-1-one] 
• 1556096-90-2 4, 4'-(4-methoxybenzylidene)-bis-[3-(2',4'-dihydroxybenzoyl)-1H-2-benzopyran-1-one] 
• 1107665-43-9 3-(2', 4'-dihydroxy-benzoyl)-1H-2-benzopyran-1-one 
• 20727-61-1 (2Z)-6-hydroxy-2-(4-methoxybenzylidene)-1-benzofuran-3(2H)-one 
• 1613190-06-9 (2Z)-6-hydroxy-2-(3,4,5-trimethoxybenzylidene)-1-benzofuran-3(2H)-one 
• 1679342-26-7 (2Z)-6-hydroxy-2-(pyridin-4-ylmethylene)-1-benzofuran-3(2H)-one 

Relevant academic research and scientific papers

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Blood-brain barrier permeable anticholinesterase aurones: Synthesis, structure-activity relationship, and drug-like properties

A series of novel aurones bearing amine and carbamate functionalities at various positions (rings A and/or B) of the scaffold was synthesized and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activities. Structure-activity relationship study disclosed several potent submicromolar acetylcholinesterase inhibitors (AChEIs) particularly aurones bearing piperidine and pyrrolidine moieties at ring A or ring B. Bulky groups particularly methoxyls, and carbamate to a lesser extent, at either rings were also prominently featured in these AChEI aurones as exemplified by the trimethoxyaurone 4-3. The active aurones exhibited a lower butyrylcholinesterase inhibition. A 3g€2-chloroaurone 6-3 originally designed to improve the metabolic stability of the scaffold was the most potent of the series. Molecular docking simulations showed these AChEI aurones to adopt favourable binding modes within the active site gorge of the Torpedo californica AChE (TcAChE) including an unusual chlorine-π interaction by the chlorine of 6-3 to establish additional bondings to hydrophobic residues of TcAChE. Evaluation of the potent aurones for their blood-brain barrier (BBB) permeability and metabolic stability using PAMPA-BBB assay and in vitro rat liver microsomes (RLM) identified 4-3 as an aurone with an optimal combination of high passive BBB permeability and moderate CYP450 metabolic stability. LC-MS identification of a mono-hydroxylated metabolite found in the RLM incubation of 4-3 provided an impetus for further improvement of the compound. Thus, 4-3, discovered within this present series is a promising, drug-like lead for the development of the aurones as potential multipotent agents for Alzheimer's disease.

Synthesis and in vitro characterization of some benzothiazole- and benzofuranone-derivatives for quantification of fibrillar aggregates and inhibition of amyloid-mediated peroxidase activity

Neurodegenerative diseases are characterized by amyloid deposition. Thioflavin T (ThT) is one of the molecules considered for detection of amyloid deposits; however, its lipophilicity is too low to cross the blood-brain barrier. Therefore, there is a strong motivation to develop suitable compounds for in vitro fibril quantification as well as for in vivo amyloid imaging. Moreover, oxidative stress (particularly, uncontrolled peroxidase activity) has frequently been reported to play a critical role in the onset/progression of some neurodegenerative disorders. In this study, we describe the synthesis of some benzothiazole and benzofuranone compounds and examine their peroxidase inhibitory properties. Furthermore, to establish the potential binding of synthesized compounds to amyloid aggregates, their in vitro binding to some non-disease related amyloidogenic proteins were characterized. Analyses of the in vitro binding studies indicated that compounds 2 and 4 bind to the amyloid structures successfully while compounds 1 and 3 showed a low affinity in binding to fibrils. Furthermore, compounds 3 and 4 were observed to inhibit amyloid-mediated peroxidase activity in a reversible un-competitive manner.

Ultrasounds-assisted synthesis of highly functionalized acetophenone derivatives in heterogeneous catalysis

A fast, general, environmentally friendly, and facile method for preparation of highly functionalized acetophenone derivatives under ultrasound irradiation in heterogeneous catalysis is presented. The ultrasound enhanced a remarkable rate of acceleration for bromination, the reaction time decrease significantly, reaction conditions are milder, the consumed energy decreases considerably and the amount of used solvents was reduced. Consequently, the ultrasounds-assisted bromination reaction could be considered ecofriendly. In the most cases under ultrasound irradiation the yields are higher, in some cases substantially. A comparative study, ultrasounds-conventional conditions was done.

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.

Photochemical α-bromination of ketones using N-bromosuccinimide: a simple, mild and efficient method

Aromatic and aliphatic carbonyl compounds undergo facile bromination with N-bromosuccinimide under UV-vis irradiation to give the corresponding α-brominated ketones in good yields, at low temperatures (30 °C), without any catalyst, catalyst support or radical initiator and within a short time.

Synthesis of α-bromoalkanones using urea-hydrogen peroxide complex and sodium bromide over silica gel-acetic acid

α-Bromoalkanones 2 have been synthesized by the reaction of alkanones 1 with UHP-NaBr over SiO2-acetic acid in solvent-free conditions under microwave irradiation.

Montmorillonite K10 - AlCl3 catalyzed enolization: A bifunctional system for selective bromination of hydroxyacetophenones

A heterogeneous system consisting of montmorillonite K-10 and AlCl3 (catalytic amount) in ethyl acetate serves as an effective catalyst for the enolization of hydroxyacetophenones thereby facilitating selective bromination of side chain using molecular bromine.

Method for treating fibrotic diseases or other indications IC

Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I: