Organobase-catalyzed tandem green hemisynthesis of novel 1,4-naphthoquinone-chromene derivative from <i>Ammodaucus leucotrichus</i> (Cosson &amp; Durieu) essential oil; antimicrobial activity and <i>in silico</i> exploration against psoriasis-associa

Chemical and biological properties of a novel 1,4-naphtoquinone-chromene derivative synthesised from perillaldehyde, major compound of <i>Ammodaucus leucotrichus</i> essential oil were evaluated. The obtained product was efficiently prepared through a tandem hemisynthesis reaction under environmentally friendly conditions (solvent-free, moderate temperature) <i>via</i> Knoevenagel condensation and Michael addition reactions, using 4-pyrolidinopyridine organobase as a catalyst. The structure of newly synthesised product (<i>HRP63)</i> was characterised using FTIR,¹H,¹³C and 2D NMR spectroscopy. Furthermore, <i>HRP63</i> was assessed for its antimicrobial activity and its potential interaction with different receptors implicated in psoriasis. The obtained results revealed moderate antibacterial activity. <i>In silico</i> molecular docking studies revealed significant inhibitory interaction of <i>HRP63</i> against TNF-α, TLR7, TLR2, and TNFR1 receptors with inhibition constants ranging from 0.74 to 0.17 µM, and free binding energies of the complexes obtained between -8.36 and -9.24 kcal/M. These results will guide future studies aimed at exploit the pharmacological profile of <i>HRP63</i> product.