Coumarins (2 H-chromen-2-ones), also known as benzopyran-2-ones, are a family of naturally occurring heterocyclic ring systems that contain a lactone moiety. Coumarins exhibit a wide range of well-studied pharmacological properties. Over the last few decades, as a result of advances in diverse oriented synthetic routes, physicochemical properties and numerous biological activities, coumarins have become globally studied molecules from various synthetic and medicinal chemists. Recently, several bioactive coumarins bearing azetidinone and thiazolidinone moieties have been found to display a range of therapeutic characteristics, including antimicrobial, anticancer, antidiabetic and anti-inflammatory properties. This review offers a brief description of the synthetic methodologies, known bioactivity and structure–activity relationships of coumarins bearing azetidinones and thiazolidinones.
The title compound (E)-1,3-dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole, C11H12N6O2, has monoclinic (C2/c) symmetry at 100 K. This triazene derivative was synthesized by the coupling reaction of 1,3-dimethylimidazolium iodide with 1-azido-4-nitro benzene in the presence of sodium hydride (60% in mineral oil) and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule consists of six-membered and five-membered rings, which are connected by a triazene moiety (–N=N—N–). In the solid-state, the molecule is found to be planar due to conjugation throughout the molecule. The extended structure shows two layers of molecules, which present weak intermolecular interactions that facilitate the stacked arrangement of the molecules forming the extended structure. Furthermore, there are several weak pseudo-cyclical interactions between the nitro oxygen atoms and symmetry-adjacent H atoms, which help to arrange the molecules.
Chihuahua State is the largest apple producer in Mexico. To prevent apples from freezing during the winter, petroleum-based fuels are used to heat the orchards. In this research work, a microorganism isolated from inside of a fuel plastic container was identified through morphological analysis as the fungus Acremonium sp. By cultivating the fungus in potato dextrose agar medium (PDA), we were able to study the biodegradation rates of three polycyclic aromatic hydrocarbons (PAHs). The isolated microorganism was incubated at 28 ºC in M9 mineral liquid medium using phenanthrene, anthracene, and pyrene as the only carbon source at a concentration of 50 µg/mL. Degradation of PAHs was monitored using an environmentally friendly reverse phase ultra-high-performance liquid chromatography (UHPLC) system, with a C18 column, 30% water acidified at 0.1% with trifluoroacetic acid, and 70% acetonitrile as the mobile phase, 40 ºC column temperature, and UV detection at 254 nm. After 30 days of biodegradation (optimal time), the final mean concentration for individual degradation experiments were 2.51 µg/mL phenanthrene, 3.02 µg/mL anthracene and 5.53 µg/mL pyrene. Those final concentrations indicate degradation percentile of 95%, 94%, and 89%, respectively. Biodegradation experiments combining all three PAHs showed similarly high degradation percentiles of 93%, 94%, and 85% for phenanthrene, anthracene, and pyrene, respectively. The dry weight average at day 30 in the individual and combined degradation experiments was 2.34 mg/mg PAHs degraded.
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