5445-86-3

Usage

InChI:InChI=1/C16H14O4/c1-11(17)14-5-3-4-6-15(14)20-16(18)12-7-9-13(19-2)10-8-12/h3-10H,1-2H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 637-69-4 4-Methoxystyrene 
• 104-93-8 p-methylanizole 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 35115-15-2 2-(propionylacetyl)phenol 
• 122-79-2 Phenyl acetate 

Downstream Products

• 121-98-2 methyl 4-methoxybenzoate 
• 118-93-4 o-hydroxyacetophenone 
• 80649-86-1 4-Methoxy-benzoic acid 2-(2-iodo-acetyl)-phenyl ester 
• 4143-72-0 1-(2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 148788-26-5 (Z)-3(2-hydroxyphenyl)-1(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol 
• 65840-97-3 3-(o-hydroxyphenyl)-5-(p-methoxyphenyl)pyrazole 
• 81902-09-2 2-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)phenol 
• 10173-84-9 2-(4-methoxybenzoyl)-3(2H)-benzofuranone 
• 80649-91-8 3-(4-Methoxy-phenyl)-1-phenyl-1H-benzo[4,5]furo[3,2-c]pyrazole 
• 36695-25-7 2'-(4-methoxybenzoyloxy)-2-bromoacetophenone 
• 61495-70-3 3-(4-methoxyphenyl)-5-(2-hydroxyphenyl)-isoxazole 
• 1433961-80-8 3-(4-hydroxybenzyl)-1-(4-methoxyphenyl)chromeno[2,3-c]pyrrol-9(2H)-one 
• 1435773-43-5 3-(4-(tert-butoxy)benzyl)-1-(4-methoxyphenyl)chromeno[2,3-c]pyrrol-9(2H)-one 
• 73910-85-7 3-bromo-2-(4-methoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Copper-catalyzed chemoselective oxidative o-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds using styrene derivatives

A novel copper-catalyzed chemoselective oxidative O-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds with a wide range of styrene derivatives are described. This approach provides an efficient chemoselective preparation of phenol, alkyl salicylate and enol esters in good to excellent yields. This method represents an alternative protocol for the classical esterification reactions.

Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone β-diketonate complexes

Difluoroboron β-diketonates complexes are highly luminescent with extensive properties such as their fluorescence both in solution and in solid state and their high molar extinction coefficients. Due to their rich optical properties, these compounds have been studied for their applications in organic electronics such as in self-assembly and applications in biosensors, bio-imaging and optoelectronic devices. The easy and fast synthesis of difluoroboron β-diketonate (BF2dbm) complexes makes their applications even more attractive. Although many different types of difluoroboron β-diketonates complexes have been studied, the cyclic flavanone analogues of these compounds have never been reported in the literature. Therefore, the present work aims to synthesize difluouroboron flavanone β-diketonate complexes, study their photophysical and electrochemical properties and assess their suitability for applications in optoelectronic devices. The synthesis was based on a Baker-Venkataraman reaction which initially provided substituted diketones, which were subsequently reacted with aldehydes to afford the proposed flavanones. The complexation was achieved by reacting flavanones and BF3·Et2O and in total 9 novel compounds were obtained. A representative difluoroboron flavanone complex was subjected to single crystal X-ray diffraction to unequivocally confirm the chemical structure. A stability study indicated only partial degradation of these compounds over a few days in a protic solvent at elevated temperatures. Photophysical studies revealed that the substituent groups and the solvent media significantly influence the electrochemical and photophysical properties of the final compounds, especially the molar absorption coefficient, fluorescence quantum yields, and the band gap. Moreover, the compounds exhibited a single excited-state lifetime in all studied solvents. Computational studies were employed to evaluate ground and excited state properties and carry out DFT and TDDFT level analysis. These studies clarify the role of each state in the experimental absorption spectra as well as the effect of the solvent.

Trypanocidal activity of flavanone derivatives

Chagas disease, also known as American trypanosomiasis, is classified as a neglected disease by the World Health Organization. For clinical treatment, only two drugs have been on the market, Benznidazole and Nifurtimox, both of which are recommended for use in the acute phase but present low cure rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology was utilized that allowed for the simultaneous use of both parasite forms responsible for human infection. The majority of the tested compounds displayed promising anti-Trypanosoma cruzi activity and the most potent flavanone bearing a nitrofuran moiety was more potent than the reference drug, Benznidazole.

Synthesis of 3,5-diarylisoxazole derivatives and evaluation of in vitro trypanocidal activity

Chagas disease is included in the neglected tropical diseases list and is endemic to 21 Latin American countries. The two drugs currently available for treating Chagas disease are nifurtimox and benznidazole and both result in many significant side effects. The study describes the synthesis and biological evaluation of 3,5-disubstituted isoxazoles. Isoxazoles were obtained by reaction of flavones and hydroxylamine and either alkylated at the free hydroxyl group and/or nitrated at the isoxazole ring. These compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against trypomastigote and amastigote forms of the parasite in T. cruzi-infected cell lineages. Benznidazole was used as a reference compound for the in vitro assay and mammalian L929 cells were employed to evaluate cytotoxicity. A majority of the compounds tested were very active and the most active isoxazole against amastigote and trypomastigotes of T. cruzi was slightly more potent than the current medicine benznidazole.

Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease

Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.

Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.

Nickel-catalyzed oxidative esterification of formamides with 1,3-dicarbonyl compounds under mild reaction conditions

Synthesis of enol carbamates was achieved via nickel-catalyzed oxidative coupling of formamides with 1,3-dicarbonyl compounds in the presence of tert-butyl hydroperoxide at 40?°C. Various derivatives of enol carbamates were synthesized by this method in good to excellent yields.

Oxidative esterification of methylarenes and 1,3-dicarbonyls catalysed by copper chloride immobilized on magnetic nanoparticles

Superparamagnetic CuCl nanoparticles were prepared and identified as an effective heterogeneous catalyst for the tandem transformation of methylarenes and 1,3-dicarbonyl compounds into the corresponding enole esters by the use of tert-butyl hydroperoxide as an external oxidant. The catalyst can be removed from the reaction medium simply by use of an external magnet. As a consequence, various derivatives of enol esters were synthesized in moderate to good yields.

Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol- 9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure

Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 A resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors.

CuO nanoparticles supported on α-Fe2O3-modified CNTs: A magnetically separable catalyst for oxidative C-O coupling of formamides with 1,3-dicarbonyl compounds This article is dedicated to memory of Rais Ali Delvari

Oxidative coupling of formamides with 1,3-dicarbonyl compounds to prepare enol carbamates was effected in the presence of CuO nanoparticles supported on α-Fe2O3-modified carbon nanotubes (CNTs at α-Fe2O3@CuO) as an environmentally friendly heterogeneous catalyst. The simple preparation, and the ability to be recycled and magnetically separated are salient features of this catalytic system.