65599-35-1Relevant academic research and scientific papers
Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone β-diketonate complexes
Paez, Elida Betania Ariza,Curcio, Sergio,Neme, Natália P.,Matos, Matheus J. S.,Correa, Rodrigo S.,Pereira, Fabio Junio,Hilário, Flaviane Francisco,Cazati, Thiago,Taylor, Jason Guy
, p. 14615 - 14631 (2020/10/02)
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
Andrade, Josimara Souza,Diogo, Gabriela Maciel,Dos Santos, Viviane Martins Rebello,Murta, Silvane Maria Fonseca,Sales, Policarpo Ademar,Taylor, Jason Guy
, (2020/01/28)
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
Sun, Dong-Wei,Jiang, Min,Liu, Jin-Tao
, p. 10797 - 10802 (2019/07/03)
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.
Green and efficient synthesis of flavones and chromones using heteropolyacids as catalyst in glycerol
Migliorero, María Belén Colombo,Palermo, Valeria,Durango, Edwin Alexis Alarcón,Holguín, Aída Luz Villa,Vázquez, Patricia Graciela,Sathicq, ángel Gabriel,Romanelli, Gustavo Pablo
, p. 826 - 832 (2018/11/06)
Organic solvents are required to carry out most organic transformations, which cause environmental pollution because of their low volatility. Glycerol, a side product obtained from biodiesel production, has emerged as a friendly solvent due to its advantageous properties. In this paper, an efficient procedure for the synthesis of flavones and chromones, using heteropolyacids as recyclable catalyst and glycerol as the solvent, is presented. The use of heteropolyacids as catalysts allows for excellent yields, easy separation and recovery, low environmental impact, and low cost. Glycerol can also be readily recovered and used over again. In addition, the presented method provides other advantages such as the low formation of waste and the replacement of corrosive mineral acids.
Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one
Han, Jie,Wang, Tao,Liang, Yong,Li, Ying,Li, Chenchen,Wang, Rui,Feng, Siqi,Zhang, Zunting
supporting information, p. 3552 - 3555 (2017/07/17)
An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.
One-pot synthesis of 3-(furan-2-yl)-4: H -chromen-4-ones from 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran catalyzed via K10 montmorillonite under solvent-free conditions
Han, Jie,Wang, Tao,Feng, Siqi,Li, Chenchen,Zhang, Zunting
supporting information, p. 4092 - 4097 (2016/07/21)
A new, concise and efficient method of one-pot synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was developed using K10 montmorillonite catalysis under solvent-free conditions. The procedure of the synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was that 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran underwent a process of α-alkoxyalkylation in the presence of K10 montmorillonite at 80 °C for 0.5 h and continuously at 120 °C for another 0.5 h. The advantages of this method were that it was solvent-free, the K10 montmorillonite was recyclable and it had an easy work-up.
Synthesis and anti-trypanosoma cruzi activity of diaryldiazepines
Menezes, Jlio Csar L.,Vaz, Luana Beatriz A.,De Vieira, Paula Melo Abreu,Fonseca, Ktia Da Silva,Carneiro, Cludia Martins,Taylor, Jason G.
, p. 43 - 51 (2015/01/30)
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.
Synthesis and discovery of (I-3,II-3)-biacacetin as a novel non-zinc binding inhibitor of MMP-2 and MMP-9
Nanjan, Pandurangan,Nambiar, Jyotsna,Nair, Bipin G.,Banerji, Asoke
, p. 3781 - 3787 (2015/07/27)
Eleven biflavones (7a-b and 9a-i) were synthesised by a simple and efficient protocol and screened for MMP-2 and MMP-9 inhibitory activities. Amongst them, a natural product-like analog, (I-3,II-3)-biacacetin (9h) was found to be the most potent inhibitor
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
Shang, Na-Na,Shao, Yong-Xian,Cai, Ying-Hong,Guan, Matthew,Huang, Manna,Cui, Wenjun,He, Lin,Yu, Yan-Jun,Huang, Lei,Li, Zhe,Bu, Xian-Zhang,Ke, Hengming,Luo, Hai-Bin
, p. 86 - 98 (2014/05/06)
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.
Synthesis of multi-functionalized chromeno[2, 3-c]pyrrol-9(2H)-ones: Investigation and application of Baker-Venkataraman rearrangement involved reactions catalyzed by 4-(Dimethylamino)pyridine
Yu, Yanjun,Hu, Yun,Shao, Weiyan,Huang, Jianing,Zuo, Yinglin,Huo, Yingpeng,An, Linkun,Du, Jun,Bu, Xianzhang
, p. 4551 - 4563 (2011/10/03)
An efficient one-pot synthesis of multi-functionalized chromeno[2, 3-c]pyrrol-9(2H)-ones from 1, 3-diaryl-1, 3-diket-ones and amino acids is described. The synthesis is based on the 4-(dimethylamino)pyridine-catalyzed Baker-Venkatara-man rearrangement and
