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J Phys Chem A ; 2019 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-30790513


In this work, we propose the synthesis of a novel bromine chalcone (E)-3-(2-bromophenyl)-1-(2phenylsulfonylamine)-phenyl)prop-2-en-1-one (BRC) that has been crystallized by slow evaporation technique. The second order molecular optical scattering and two-photon absorption(2PA) spectrumof the BRC molecule dissolved in Dimethyl Sulfoxide (DMSO) were evaluated by using Hyper Rayleigh Scattering and femtosecond tunable Z-Scan techniques. The first order hyperpolarizability of BRC dissolved in DMSO was estimated by using a simplified two-level model, in which one- and two-photon absorption parameters were used as input information to the model. The BRC crystal was characterized from single crystal X-ray diffraction (DRX) and spectroscopy analyzes. Also, the thermogravimetric analyses and the fluorescence spectra were obtained. In addition, an ab-initio calculation method, which includes the Møller-Plesset Perturbation Theory (MP2) and the Density Functional Theory (DFT) at CAM-B3LYP level,was used to estimate the crystal linear refractive index and the third-order electric susceptibility. Also, the average first hyperpolarizability of BRC molecules dissolved in DMSO was calculated and compared with the experimental results. The obtained values are good and qualify BRC crystal as a potential candidate for application in nonlinear optical devices.

Spectrochim Acta A Mol Biomol Spectrosc ; 204: 685-695, 2018 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-29982160


Chalcones and their derivatives exhibit numerous pharmacological activities such as antibacterial, antifungal, cytotoxic, antinociceptive and anti-inflammatory. Recently, they have been assessed aiming for novel application in nonlinear optics and in the treatment of immune diseases and cancers. In this study, we investigate the optical properties of synthetic chalcona 1E,4E-1-(4-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one (CAB7ß) and its antiangiogenic potential using the chorioallantoic membrane (CAM) with the S180 sarcoma cell line. Experimental and theoretical results show intense absorption in the UVA-UVC region, which is associated with a π → π* transition with intramolecular charge transfer from the trimethyl-cyclohexen-1-yl ring to the chlorophenyl ring. Quantum chemical calculations of the first hyperpolarizability, accounting for both solvent and frequency dispersion effects, are in very good concordance with hyper-Rayleigh scattering measurements. In addition, two-photon absorption allowed band centered at 650 nm was observed. Concerning antiangiogenic activity, CAB7ß causes a significant reduction in the total number, junctions, length and caliber of blood vessels stimulated by S180 cells reducing the presence of blood vessels, inflammatory cells and others elements related to angiogenic process. It is found that CAB7ß is a versatile compound and a promising candidate for linear and nonlinear optical applications, in therapy against sarcoma and phototherapy.

Inibidores da Angiogênese/farmacologia , Chalcona/análogos & derivados , Chalcona/farmacologia , Neovascularização Patológica , Linhagem Celular Tumoral , Membrana Corioalantoide/citologia , Humanos , Modelos Biológicos , Neovascularização Patológica/patologia , Neovascularização Patológica/prevenção & controle
Arch Pharm (Weinheim) ; 351(7): e1700386, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29775221


The stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4'-hydroxychalcone 1 and its bis-Mannich derivative 2 was investigated at different pH values (pH 3.2, 6.1, 7.4, and 8.0). The stereochemical outcome of the reactions was evaluated by HPLC-UV-Vis method. Under strongly acidic conditions (pH 3.2), an unexpected diastereoselective addition of GSH onto the bis-Mannich derivative 2 was observed. Such a selectivity could not be observed in the similar reaction of 2 with N-acetylcysteine. The observed stereoselectivity can be rationalized by ion-pair formation between the protonated Mannich nitrogens and the deprotonated GSH(glutamate)-carboxylate. To the best of our knowledge, this is the first example of reagent-induced asymmetric induction in Michael-type additions of thiols.

Chalconas/química , Cromatografia Líquida de Alta Pressão/métodos , Glutationa/química , Acetilcisteína/química , Concentração de Íons de Hidrogênio , Bases de Mannich/química , Estereoisomerismo
Chem Biodivers ; 10(11): 1999-2006, 2013 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-24243608


A series of chalcone derivatives, 1-15, were prepared by Claisen-Schmidt condensation and evaluated for their cytotoxicities on tumor cell lines and also against proteolytic enzymes such as cathepsins B and K. Of the compounds synthesized, (E)-3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one (12), (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (13), (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (14), and (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one (15) showed significant cytotoxicities. The most effective compound was 15, which showed high cytotoxic activity with an IC50 value lower than 1 µg/ml, and no selectivity on the tumor cells evaluated. Substituents at C(4) of ring B were found to be essential for cytotoxicity. In addition, it was also demonstrated that some of these chalcones are moderate inhibitors of cathepsin K and have no activity against cathepsin B.

Antineoplásicos/química , Antineoplásicos/farmacologia , Catepsina B/antagonistas & inibidores , Catepsina K/antagonistas & inibidores , Chalcona/análogos & derivados , Chalcona/farmacologia , Catepsina B/metabolismo , Catepsina K/metabolismo , Linhagem Celular Tumoral , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Humanos , Neoplasias/tratamento farmacológico , Neoplasias/enzimologia
Acta Crystallogr C ; 69(Pt 3): 267-72, 2013 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-23459353


The structures of two arylsulfonamide para-alkoxychalcones, namely, N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C22H19NO4S, (I), and N-{4-[(E)-3-(4-ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C23H21NO4S, (II), reveal the effect of the inclusion of one -CH2- group between the CH3 branch and the alkoxy O atom on the conformation and crystal structure. Although the molecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent molecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H...π and π-π interactions, while only C-H...π contacts occur in the structure of (II). The role of the additional methylene group in the crystal packing can also be seen in the fact that the alkoxy O atom is an acceptor in nonclassical hydrogen bonds only in the para-ethoxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H...O hydrogen-bonded ribbons, a synthon commonly found in related compounds.

Chalconas/química , Sulfonamidas/química , Cristalografia por Raios X , Ligação de Hidrogênio , Conformação Molecular , Estrutura Molecular
Acta Crystallogr C ; 67(Pt 7): o226-9, 2011 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-21727630


Two arylsulfonamide derivatives, N-(4-acetylphenyl)benzenesulfonamide, C(14)H(13)NO(3)S, and N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide, C(14)H(11)Cl(2)NO(3)S, differing by the absence or presence of two chloro substituents on one of the phenyl rings, were synthesized and characterized in order to establish structural relationships and the role of chloro substitution on the molecular conformation and crystal assembly. Both arylsulfonamides form inversion-related dimers through C-H···π and π-π interactions. These dimers pack in a similar way in the two structures. The substitution of two H atoms at the 2- and 5-positions of one phenyl ring by Cl atoms did not substantially alter the molecular conformation or the intermolecular architecture displayed by the unsubstituted sulfonamide. The structural information controlling the assembly of such compounds in their crystal phases is in the (phenyl)benzenesulfonamide molecular framework.

Cloro/química , Sulfonamidas/química , Cristalografia por Raios X , Ligação de Hidrogênio , Modelos Moleculares , Conformação Molecular , Estrutura Molecular