Chalcone-quinolinone hybrid compounds, as well as the synthesis of such compounds, have few reports in the literature. Such compounds may be quite useful in therapeutics, since various biological activities are reported for both chalcones and quinolinones. In the present work, several novel chalcone-quinolinone compounds have been synthesized. The reaction conditions developed allowed to obtain the compounds in...
Four new alkaloids, Brazoides A-D, together with three known compounds squalene, β-sitosterol and lupeol, were isolated from leaves of Justicia gendarussa. These structures were established by spectrometric techniques, mainly high-resolution electrospray ionization mass spectrometry (HRESIMS) and 1D and 2D nuclear magnetic resonance (NMR), including comparative analysis with literature values. Structural determ...
Natural α,β-amyrins were isolated from endemic Brazilian Esenbeckia grandiflora Mart., and eight synthetic derivatives were obtained by esterification reactions with bromo acetate, followed by amine treatment. The structures of the all compounds were confirmed by 1H and 13C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and high-resolution mass spectrometry (HRMS) data analysis. The derivat...
Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z' > 1 are found in three compounds as a consequence of co...
Several studies have demonstrated the cytotoxic potential of nor-β-lapachone derivative against cancer cells. Considering nor-β-lapachone as an important prototype, a set of new 3-substituted nor-β-lapachones was synthesized by a new synthetic route that involves the use of synthetic intermediate generated for coupling with several nucleophiles containing the carbohydrate and 2H-pyrazole substituent moieties. A...
The phytochemical investigation of the ethanol extract from leaves of Lecythis pisonis Cambess., Lecythidaceae, resulted in the isolation of seven triterpenes: α- and β-amyrin, uvaol and erythrodiol, ursolic and oleanolic acids and 3β-friedelinol, as well as a mixture of sitosterol and stigmasterol steroids and a diterpene (E)-phytol. The structures of these compounds were identified by¹H and 13C NMR spectral a...
Ethyl acetate extracts of cultures grown in liquid Czapek and on solid rice media of the fungal endophyte Fusarium oxysporum SS46 isolated from the medicinal plant Smallanthus sonchifolius (Poepp.) H. Rob., Asteraceae, exhibited considerable cytotoxic activity when tested in vitro against human cancer cells. Chromatographic separation yielded anhydrofusarubin (1) and beauvericin (2) that were identified based o...
Brain cancer is the second neurological cause of death. A simplified animal brain tumor model using W256 (carcinoma 256, Walker) cell line was developed to permit the testing of novel treatment modalities. Wistar rats had a cell tumor solution inoculated stereotactically in the basal ganglia (right subfrontal caudate). This model yielded tumor growth in 95% of the animals, and showed absence of extracranial met...
Cytotoxic activity of eight plant extracts, native from the Mid-West of Brazil comprising Cerrado, Pantanal and semideciduous forest, was evaluated for MDA-MB-435, SF-295, and HCT-8 cancer cell strains. A single 100 µg.mL-1 dose of each extract was employed with 72 h of incubation for all tests. Doxorubicin (1 µg.mL-1) was used as the positive control and the MTT method was used to detect the activity. Cytotoxi...
Novel 2-(R-phenyl)amino-3-(2-methyl-propenyl)-[1,4]-naphthoquinones (R = H, 4-OMe, 4-Ferrocenyl, 4-Me, 3-Me, 4-I, 3-I, 4-CN, 3-CN, 4-NO2 and 3-NO2) derived from nor-lapachol [2-hydroxy-3-(2-methylpropenyl)-1,4-naphthoquinone] were obtained in good yields. Their structures were proposed on the basis of a single crystal X-ray diffraction study (R = OMe, 2b), ¹H and 13C NMR studies and calculations using the B3LYP...