Naslov
Environmentally friendly approach to Knoevenagel condensation of Rhodanine in choline chloride: urea deep eutectic solvent and QSAR studies on their antioxidant activity
(Environmentally friendly approach to Knoevenagel condensation of Rhodanine in choline chloride: urea deep eutectic solvent and QSAR studies on their antioxidant activity)

Autori
Molnar, Maja ; Brahmbhatt, Harshad ; Rastija, Vesna ; Pavić, Valentina ; Komar, Mario ; Karnaš, Maja ; Babić, Jurislav

Izvornik
Molecules (1420-3049) 23 (2018), 8; 1897, 15

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
rhodanine ; deep eutectic solvents ; Knoevenagel condensation ; antioxidant activity ; QSAR ; molecular docking ; tyrosinase

Sažetak
A series of rhodanine derivatives was synthesized in the Knoevenagel condensation of rhodanine and different aldehydes using choline chloride:urea (1:2) deep eutectic solvent. This environmentally friendly and catalyst free approach was very effective in the condensation of rhodanine with commercially available aldehydes, as well as the ones synthesized in our laboratory. All rhodanine derivatives were subjected to 1, 1-diphenyl-2- picrylhydrazyl radical (DPPH) scavenging activity investigation and quantitative structure- activity relationship (QSAR) studies were performed to elucidate their structure-activity relationship. The best multiple linear QSAR model demonstrate a stability in the internal validation and Y- randomization (R 2 = 0.81 ; F = 24.225 ; Q2 loo = 0.72 ; R 2 Yscr = 0.148). Sphericity of the molecule, ratio of symmetric atoms enhanced atomic mass along the principle axes in regard to total number of atoms in molecule, and 3D distribution of the atoms higher electronegativity (O, N, and S) in molecules are important characteristic for antioxidant ability of rhodanine derivatives. Molecular docking studies were carried out in order to explain in silico antioxidant studies, a specific protein tyrosine kinase (2HCK). The binding interactions of the most active compound have shown strong hydrogen bonding and van der Waals interactions with the target protein.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Prehrambena tehnologija

POVEZANOST RADA