Phenylphosphonic acid is an efficient, friendly and reusable heterogeneous catalyst for the synthesis of α-aminophosphonates through a ‘one-pot’ three-component reaction of amines, carbonyl compounds and dialkyl phosphites under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines, aliphatic and aromatic aldehydes and aliphatic ketones. It also enabled the synthesis of α-aminophosphonates in large scale, clean conversion, easy workup and purification. Excellent results were obtained in each case obtaining the desire compounds in moderate to good yields.
1 February 2017 in Bioorganic & Medicinal Chemistry Letters
trans-Cinnamic acid was synthesized under microwave irradiation, and it was used for the removal of copper, a toxic metal found in industrial wastewater, from synthetic polluted aqueous solutions. Copper removal is more favorable at pH 5 and was enhanced by increasing the copper initial concentration, reaching a maximum uptake capacity of 389.5 mg/g, which is higher than those reported in the literature. Temperature exhibited a negligible effect on the removal of copper by trans-cinnamic acid. The isotherm equilibrium uptake data were found to be described by the Langmuir model. In addition, the study of the removal kinetics shows that the uptake of copper by trans-cinnamic acid follows pseudo-first order kinetics, and equilibrium is attained at approximately 30 min. Based on the X-ray photoelectron spectroscopy, X-ray diffraction, scanning transmission electron microscopy, and Fourier-transform infrared spectroscopy studies, a copper–cinnamic acid complex [Cu(CA)2] is formed during the removal process. The reusability of this coordination compound was investigated using HCl, HNO3, and NaOH 0.1 M as desorption eluents; HCl was capable of completely desorbing copper from [Cu(CA)2], and trans-cinnamic acid was recovered as the trans-isomer. Alternatively, the [Cu(CA)2] was used to remove octamethylcyclotetrasiloxane from gaseous streams for biogas purification, obtaining an adsorption capacity of 3.37 mg/g. These promising results demonstrate the feasibility of copper removal by trans-cinnamic acid because of its high uptake capacity and potential reusability.
The Scedosporium genus is an emerging pathogen with worldwide prevalence and high mortality rates that gives multidrug resistance to antifungals; therefore, pharmacological alternatives must be sought for the treatment of diseases caused by this fungus. In the present project, six new α-aminophosphates were synthesized by the Kabachnik–Fields multicomponent reaction by vortex agitation, and six new monohydrolyzed α-aminophosphonic acids were synthesized by an alkaline hydrolysis reaction. Antifungal activity was evaluated using the agar diffusion method as an initial screening to determine the most active compound compared to voriconazole; then it was evaluated against 23 strains of the genus Scedosporium following the M38-A2 protocol from CLSI (activity range: 648.76–700 µg/mL). Results showed that compound 5f exhibited the highest antifungal activity according to the agar diffusion method (≤1 mg/mL). Cytotoxicity against healthy COS-7 cells was also evaluated by the MTT assay and it was shown that compound 5f exhibits a lower toxicity in comparison to voriconazole at the same concentration (1000 µM). A docking study was conducted afterwards, showing that the possible mechanism of action of the compound is through the inhibition of allosteric 14-α-demethylase. Taking these results as a basis, 5f is presented as a compound with attractive properties for further studies.