Taking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.
More and more importance has been given lately to the use of environment-friendly materials. Natural resins of vegetal, animal or mineral origin are increasingly employed. This article studies the properties of hybrid composites, obtained by formulating the natural resin Dammar with epoxy resin. The Dammar volume proportion was of 60%, 70% and 80%, respectively. The article is divided in two parts. In the first part, the chemical composition of the natural resin Dammar is analysed. Therefore, the substance was purified by chromatography. The structure and purity of the isolated substances were investigated by 1H-NMR, 13C-NMR experiments and mass analysis. The second part concentrates on structural characterization and on some mechanical properties of the three different hybrid composites. For this purpose, the characteristic curves, modulus of elasticity, tensile strength and elongation at break were measured. Graphic
1 July 1993 in Phosphorus, Sulfur, and Silicon and the Related Elements