The structure transformation of Mg-CUK-1 due to the confinement of H2O molecules was investigated. Powder X-ray diffraction (PXRD) patterns were collected at different H2O loadings and the cell parameters of the H2O-loaded Mg-CUK-1 material were determined by the Le Bail strategy refinements. A bottleneck effect was observed when one hydrogen-bonded H2O molecule per unit cell (18% relative humidity (RH)) was confined within Mg-CUK-1, confirming the increase in the CO2 capture for Mg-CUK-1.
A series of 12 polysubstituted pyrrolo[3,4-b]pyridin-5-ones were synthesized via a one-pot cascade process (Ugi–3CR/aza Diels-Alder/N-acylation/decarboxylation/dehydration) and studied in vitro using human epithelial cervical carcinoma SiHa, HeLa, and CaSki cell line cultures. Three compounds of the series exhibited significative cytotoxicity against the three cell lines, with HeLa being the most sensitive one. Then, based on these results, in silico studies by docking techniques were performed using Paclitaxel as a reference and αβ-tubulin as the selected biological target. Worth highlighting is that strong hydrophobic interactions were observed between the three active molecules and the reference drug Paclitaxel, to the αβ-tubulin. In consequence, it was determined that hydrophobic–aromatic moieties of bioactive compounds and Paclitaxel play a key role in making stronger interactions to the ligand–target complex. A quantitative structure activity relationship (QSAR) study revealed that the six membered rings are the most significant molecular frameworks, being present in all proposed models for the in vitro-studied cell lines. Finally, also from the docking interpretation, a ligand-based pharmacophore model is proposed in order to find further potential polyheterocyclic candidates to bind stronger to the αβ-tubulin.
A. Synthesis of New bis-furanylpyrrolo[3,4-b]pyridin-5-ones via the Ugi-Zhu Reaction and Docking Studies on the Main Protease (M Pro ) from SARS-CoV-2. Chem. Proc. 2022,
Eight novel 2-aminonitrile oxazoles were synthesized efficiently and quickly via an Ugi reaction in its three-component version in moderate to good yields (61-79%) at room temperature or in good to excellent yields (73-90%) under ultrasound irradiation (USI) conditions. It is noteworthy that not only the yields were improved by using USI, also the reaction times decreased considerably, from 3 hours (at r.t.) to 1 hour (under USI), depending on the substituents in the final products, which are highly functionalized because have an amino group, a nitrile group, an oxazole group and a very reactive methylene-linked biaryl. In this context, they can be used for further condensations, cyclizations and/or functionalizations toward a variety of compounds with potential applications in several fields of knowledge like optics, material science and medicinal chemistry.
The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR).
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