The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. New substances are needed in order to treat different pathologies affecting the health of humans and animals, and these new compounds should be safe, effective and have the fewest side effects possible. Some functional groups are known for having biological activity; in this matter, the nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules. Nitro compounds display a wide spectrum of activities that include antineoplastic, antibiotic, antihypertensive, antiparasitic, tranquilizers and even herbicides, among many others. Most nitro molecules exhibit antimicrobial activity, and several of the compounds mentioned in this review may be further studied as lead compounds for the treatment of H. pylori, P. aeruginosa, M. tuberculosis and S. mutans infections, among others. The NO2 moiety triggers redox reactions within cells causing toxicity and the posterior death of microorganisms, not only bacteria but also multicellular organisms such as parasites. The same effect may be present in humans as well, so the nitro groups can be considered both a pharmacophore and a toxicophore at the same time. The role of the nitro group itself also has a deep effect on the polarity and electronic properties of the resulting molecules, and hence favors interactions with some amino acids in proteins. For these reasons, it is fundamental to analyze the recently synthesized nitro molecules that show any potential activity in order to develop new pharmacological treatments that enhance human health.
BACKGROUND Several pharmaceuticals have been detected as minor pollutants in industrial waste, surface and ground water. Among these compounds, antacids are the most widely consumed. Recently, advanced oxidation processes (AOPs) have been acknowledged as very promising methodologies to degrade and remove pharmaceutical compounds from water. RESULTS The advanced oxidation of omeprazole (OME) promoted by the TiO2/UV system in aqueous medium was investigated. Monitoring this reaction by HPLC and TOC, it was demonstrated that while degradation of OME is quite efficient under these conditions, its mineralization is not complete. Continuous monitoring by IR spectroscopy demonstrated the breaking of the OME structure giving rise to two main intermediate groups, pyridine and benzimidazole derivatives. These aromatic compounds were eventually converted into trans‐unsaturated carboxylic and amino acids. A total of 14 intermediate reaction products were identified by GC‐MS analysis. Among these, the hydroxylated compounds stand out since they become more abundant as time moves forward, as evidenced by FT‐IR and UV–vis analysis. GC‐MS and FT‐IR studies indicate the presence of nitro derivatives such as nitrophenol and nitrobenzimidazole in the reaction mixtures. CONCLUSION Based on these experimental results, a total mechanism for photocatalytic oxidation of OME is proposed indicating benzimidazole and alkyl pyridine degradation pathways. Utilizing several analytical techniques, some fundamental aspects of the oxidative mechanism of OME were elucidated such as mode and sites of oxidation. Studies on degradation mechanisms are fundamental for future applications of photocatalysis in the removal of pharmaceutical compounds from residual water. © 2017 Society of Chemical Industry
1,2,3-triazoles are popular heterocycles employed in material sciences and medicinal chemistry as they show antiviral, antibacterial, anti-HIV, antitubercular, and antifungal activities. Triazoles are appealing due to their stability and interesting click chemistry properties. The Cu(I) catalyzed reaction between azides and alkynes affords the 1,4- disubstituted derivative exclusively becoming a useful synthetic tool. However, one of the main drawbacks of the catalyzed reaction is the need to use Cu(I), which is unstable at standard conditions and rapidly oxidizes to the non-active Cu(II). The most common approach when synthesizing 1,4-disubstituted-1,2,3-triazoles is to reduce Cu in situ employing inorganic Cu salts and a reducing agent. The resulting Cu(I) needs to be further stabilized with organic ligands for the reaction to take place. The aim of homogeneous catalysis is to produce a ligand with a dual function both in reducing and stabilizing Cu(I) without interfering in the overall reaction. Instead, heterogeneous catalysis offers more options when supporting Cu on nanoparticles, complexes, and composites yielding the desired 1,2,3-triazoles in most cases without the need of a reducing agent under green solvents such as ethanol and water. The catalytic activity of Ag, Ru, and Ce is also discussed. This review exemplifies how the use of homogeneous and heterogeneous catalysts offers new and green methodologies for the synthesis of 1,2,3-triazole derivatives. The materials supporting Cu show catalytic properties like high surface area, acid-base sites or phase transfer. Although there is no ideal catalyst, Cu remains the most effective metal since it is economical, abundant and readily available.
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