Abstract
β-Enaminonitrile (4), was created using Ultrasonic irradiation under 60 W and interval of two minutes at room temperature. Single crystal X-ray diffraction and multi-nuclear NMR spectroscopy were used to confirm the product. The crystallographic properties of 4 were characterized by the 3D Hirshfeld surface analysis, which reveals the presence of weak intermolecular force zones. Density Functional Theory (DFT) studies indicating that the (HOMO) is predominantly located over the nitrophenyl ring. In contrast, the (LUMO) is mainly situated over the chromene portion. The localization of these orbitals suggests potential sites for nucleophilic and electrophilic attacks, highlighting the reactivity of the compound. The docking study has shown that kojic acid exhibits consistent inhibitory activity on tyrosinase, making it a suitable reference for evaluating new inhibitors. The comparison of the binding mode of a test 4 with that of kojic acid can indicate a more potent inhibition activity for 4 which demonstrates a stronger or more efficient interaction with the tyrosinase active site.
Original language | English |
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Article number | 140289 |
Journal | Journal of Molecular Structure |
Volume | 1322 |
DOIs | |
Publication status | Published - Feb 15 2025 |
Keywords
- 4H-Benzo[h]chromene
- DFT studies
- Molecular docking
- Tyrosinase inhibitor
- Ultrasound synthesis
ASJC Scopus subject areas
- Analytical Chemistry
- Spectroscopy
- Organic Chemistry
- Inorganic Chemistry