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- Title
Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2- a ]Pyrimidine-3-Carboxylate.
- Authors
Lahmidi, Sanae; Anouar, El Hassane; Ettahiri, Walid; El Hafi, Mohamed; Lazrak, Fatima; Alanazi, Mohammed M.; Alanazi, Ashwag S.; Hefnawy, Mohamed; Essassi, El Mokhtar; Mague, Joel T.
- Abstract
A retro-Claisen reaction of 1-(4-oxo-4H-pyrido [1,2-a]pyrimidin-3-yl)butane-1,3-dione, 3, in the presence of potassium hydroxide and 4-dimethylamino-pyridine has been carried out, leading to 4-(dimethylamino)pyridin-1-ium 2-methyl-4-oxo-pyrido [1,2-a]pyrimidine-3-carboxylate 5. A plausible mechanism explaining the formation of the title compound has been proposed. A single-crystal X-ray diffraction analysis confirms the crystal structure of the isolated organic salt (5). In the crystal, the title compound adopts a layered structure where there are stacks of cations and anions formed by slipped π-stacking interactions. These stacks are linked by regions consisting of water molecules that are hydrogen-bonded together. DFT and Hirshfeld surface analysis supported the experimental results of the molecular geometry and the intercontacts between different units in the crystal. The druglikeness, ADMET properties, and predicted targets were investigated, and the observed results suggest that 5 may act as a carbonic anhydrase I inhibitor. The assumption is confirmed by docking 5 into the active binding site of carbonic anhydrase, which shows it to have good binding affinities and to form stable complexes with the active residues of carbonic anhydrase I.
- Subjects
MOLECULAR docking; CARBONIC anhydrase inhibitors; CARBONIC anhydrase; MOLECULAR shapes; POTASSIUM hydroxide
- Publication
Crystals (2073-4352), 2023, Vol 13, Issue 9, p1333
- ISSN
2073-4352
- Publication type
Article
- DOI
10.3390/cryst13091333