4010-26-8

Upstream product

• 106-43-4 para-chlorotoluene 
• 118-93-4 o-hydroxyacetophenone 
• 99-94-5 p-Toluic acid 
• 122-79-2 Phenyl acetate 
• 874-60-2 4-methyl-benzoyl chloride 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 619-41-0 4-(bromoacetyl)toluene 
• 106-42-3 para-xylene 
• 104-87-0 4-methyl-benzaldehyde 
• 108-88-3 toluene 
• 35115-15-2 2-(propionylacetyl)phenol 

Downstream Products

• 5067-22-1 1-(2-hydroxyphenyl)-3-(4-methylphenyl)propane-1,3-dione 
• 204908-14-5 2-(4'-methylphenyl)-3-methylbenzofuran 
• 118092-41-4 2-(4-Dibromomethyl-phenyl)-chromen-4-one 
• 58996-67-1 2-(4'-formyl-phenyl)-4H-1-benzopyran-4-one 
• 263153-73-7 3-(methoxymethyl)oxy-4'-(bromomethyl)flavone 
• 263154-44-5 3-(methoxymethyl)oxy-4'-methylflavone 
• 19275-68-4 3-Hydroxy-4'-methylflavone 
• 41255-30-5 4'-methylflavone 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 118-93-4 o-hydroxyacetophenone 

Relevant academic research and scientific papers

Synthesis and modification of light-sensitive 3-acyl-2-hetarylchromones containing bromomethyl group in the acyl fragment

A synthesis of photosensitive 3-acyl-2-hetarylchromones containing bromomethyl group in the 3-aroyl fragment and their further modification by the reactions with N-, S- and O-nucleophiles are described. A dependence of spectral properties from the structu

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.

Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride

A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.

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.

Directing group assisted copper-mediated aroylation of phenols using 2-bromoacetophenones

A new directing group assisted method for the synthesis of aryl esters is described. In this Cu(ii)-mediated reaction, 2-formylphenols and 2-acetylphenols are easily converted into aryl esters via treatment with a new aroylating agent 2-bromoacetophenone.

One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone-and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations 3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected. Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 3 μM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 μM, whereas normal peripheral blood mononuclear cells were not affected.

Synthesis and anti-trypanosoma cruzi activity of diaryldiazepines

Chagas disease is a so-called "neglected disease" and endemic to Latin America. Nifurtimox and benznidazole are drugs that have considerable efficacy in the treatment of the acute phase of the disease but cause many significant side effects. Furthermore, in the Chronic Phase its efficiency is reduced and their therapeutic effectiveness is dependent on the type of T. cruzi strain. For this reason, the present work aims to drive basic research towards the discovery of new chemical entities to treat Chagas disease. Differently substituted 5,7-diaryl-2,3-dihydro-1,4-diazepines were synthesized by cyclocondensation of substituted flavones with ethylenediamine and tested as anti-Trypanosoma cruzi candidates. Epimastigotes of the Y strain from T. cruzi were used in this study and the number of parasites was determined in a Neubauer chamber. The most potent diaryldiazepine that reduced epimastigote proliferation exhibited an IC50 value of 0.25 μM, which is significantly more active than benznidazole.

Directing group assisted copper-catalyzed chemoselective O-aroylation of phenols and enols using alkylbenzenes

By using alkylbenzenes as aroyl surrogates, copper(II) catalyzed chemoselective O-aroylations of 1,3-dicarbonyl compounds and phenolic-OH ortho to carbonyl (-CHO,-COR) groups have been achieved. A dual mechanism operating in tandem for these transformations has been supported by a crossover experiment.