1469-94-9Relevant articles and documents
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)
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.
Catalytic and stoichiometric flavanone oxidation mediated by nonheme oxoiron(iv) complexes as flavone synthase mimics: Kinetic, mechanistic and computational studies
Turcas, Ramona,Kripli, Balázs,Attia, Amr A. A.,Lakk-Bogáth, Dóra,Speier, Gábor,Giorgi, Michel,Silaghi-Dumitrescu, Radu,Kaizer, József
, p. 14416 - 14420 (2018)
The present study describes the first example of the stoichiometric and catalytic oxidation of flavanone by synthetic nonheme oxoiron(iv) complexes and their precursor iron(ii) complexes with m-CPBA as the terminal oxidant. These models, including detailed kinetic, mechanistic and computational studies, may serve as the biomimics of flavone synthase (FS) enzymes.
Comparison of nonheme manganese‐ and iron‐containing flavone synthase mimics
Juraj, Natalija Pantalon,Kaizer, József,Kirin, Sre?ko I.,Lakk‐bogáth, Dóra,Meena, Bashdar I.,Peri?, Berislav
, (2021/06/16)
Heme and nonheme‐type flavone synthase enzymes, FS I and FS II are responsible for the synthesis of flavones, which play an important role in various biological processes, and have a wide range of biomedicinal properties including antitumor, antimalarial, and antioxidant activities. To get more insight into the mechanism of this curious enzyme reaction, nonheme structural and functional models were carried out by the use of mononuclear iron, [FeII(CDA‐BPA*)]2+ (6) [CDA‐BPA = N,N,N’,N’‐tetrakis‐(2‐pyridylmethyl)‐cyclohexanediamine], [FeII(CDA‐BQA*)]2+ (5) [CDA‐BQA = N,N,N’,N’‐tetrakis‐(2‐quinolilmethyl)‐cyclohexanediamine], [FeII(Bn‐TPEN)(CH3CN)]2+ (3) [Bn‐ TPEN = N‐benzyl‐N,N’,N’‐tris(2‐pyridylmethyl)‐1,2‐ diaminoethane], [FeIV(O)(Bn‐TPEN)]2+ (9), and manganese, [MnII(N4Py*)(CH3CN)]2+ (2) [N4Py* = N,N‐bis(2‐pyridylmethyl)‐1,2‐di(2‐pyridyl)ethyl-amine)], [MnII(Bn‐TPEN)(CH3CN)]2+ (4) complexes as catalysts, where the possible reactive inter-mediates, high‐valent FeIV(O) and MnIV(O) are known and well characterised. The results of the catalytic and stoichiometric reactions showed that the ligand framework and the nature of the metal cofactor significantly influenced the reactivity of the catalyst and its intermediate. Comparing the reactions of [FeIV(O)(Bn‐TPEN)]2+ (9) and [MnIV(O)(Bn‐TPEN)]2+ (10) towards flavanone under the same conditions, a 3.5‐fold difference in reaction rate was observed in favor of iron, and this value is three orders of magnitude higher than was observed for the previously published [FeIV(O)(N2Py2Q*)]2+ [N,N‐bis(2‐quinolylmethyl)‐1,2‐di(2‐pyridyl)ethylamine] species.
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.
