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1.
ACS Appl Mater Interfaces ; 15(26): 32024-32036, 2023 Jul 05.
Article En | MEDLINE | ID: mdl-37340706

We describe the proof of concept of a portable testing setup for the detection of triacetone triperoxide (TATP), a common component in improvised explosive devices. The system allows for field testing and generation of real-time results to test for TATP vapor traces in air by simply using circulation of the air samples through the sensing mechanism under the air conditioning system of an ordinary room. In this way, the controlled trapping of the analyte in the chemical sensor gives reliable results at extremely low concentrations of TATP in air under real-life conditions, suitable for daily use in luggage storage for airlines or a locker room for a major sporting event. The reported fluorescent methodology is very sensitive and selective, allowing for the trapping of triacetone triperoxide in the chemical sensor to give reliable results at very low concentrations in air under ambient conditions, by comparing the fluorescence of the material before and after exposition to TATP traces in air.

2.
Molecules ; 26(11)2021 May 22.
Article En | MEDLINE | ID: mdl-34067439

Ezetimibe is a well-known drug that lowers blood cholesterol levels by reducing its absorption in the small intestine when joining to Niemann-Pick C1-like protein (NPC1L1). A ligand-based study on ezetimibe analogues is reported, together with one-hit synthesis, highlighted in the study. A convenient asymmetric synthesis of (2S,3S)-N-α-(R)-methylbenzyl-3-methoxycarbonylethyl-4-methoxyphenyl ß-lactam is described starting from Baylis-Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent inversion of ester and acid functionality paves the way to the lactam core after monodebenzylation and lactam formation. It also shows interesting results when it comes to a pharmacophore study based on ezetimibe as the main ligand in lowering blood cholesterol levels, revealing which substituents on the azetidine-2-one ring are more similar to the ezetimibe skeleton and will more likely bind to NPC1L1 than ezetimibe.


Chemistry Techniques, Synthetic , Drug Design , Ezetimibe/analogs & derivatives , Ezetimibe/chemical synthesis , Alleles , Amides/chemistry , Amino Acids/chemistry , Anticholesteremic Agents/administration & dosage , Anticholesteremic Agents/chemical synthesis , Cholesterol/blood , Humans , Ligands , Magnetic Resonance Spectroscopy , Membrane Transport Proteins/metabolism , Molecular Docking Simulation , Pyridines/chemistry , Stereoisomerism
3.
Molecules ; 26(5)2021 Mar 05.
Article En | MEDLINE | ID: mdl-33807775

We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV-vis, fluorescence, NMR, and quantum mechanics calculations, and their prospective use as multi-signal reporters in a smart label for fish freshness.


Amides/chemical synthesis , Amines/chemistry , Fish Products/analysis , Fluorescent Dyes/chemical synthesis , Food Analysis/methods , Amides/chemistry , Animals , Electron Spin Resonance Spectroscopy , Fluorescence , Fluorescent Dyes/chemistry , Free Radicals/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Perciformes
4.
Acta Crystallogr E Crystallogr Commun ; 73(Pt 4): 503-506, 2017 Apr 01.
Article En | MEDLINE | ID: mdl-28435707

The title compound, C22H25NO5, was prepared by CAN [cerium(IV) ammonium nitrate] oxidation of the corresponding ß-lactam. The dihedral angle between the benzene rings is 13.3 (4)° and the C-N-C(=O)-C torsion angle is 176.1 (6)°. In the crystal, amide-C(4) N-H⋯O and reinforcing C-H⋯O hydrogen bonds link the mol-ecules into infinite [010] chains. Further C-H⋯O hydrogen bonds cross-link the chains in the c-axis direction.

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