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Molecules 2017, 22(9), 1482; doi:10.3390/molecules22091482

Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies

1
Faculty of Food Technology Osijek, Josip Juraj Strossmayer University of Osijek, Franje Kuhaca 20, Osijek 31000, Croatia
2
Faculty of Agriculture in Osijek, Josip Juraj Strossmayer University of Osijek, Vladimira Preloga 1, Osijek 31000, Croatia
*
Author to whom correspondence should be addressed.
Received: 8 August 2017 / Revised: 29 August 2017 / Accepted: 2 September 2017 / Published: 5 September 2017
(This article belongs to the Special Issue Versatile Coumarins)
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Abstract

Deep eutectic solvents, as green and environmentally friendly media, were utilized in the synthesis of novel coumarinyl Schiff bases. Novel derivatives were synthesized from 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide and corresponding aldehyde in choline chloride:malonic acid (1:1) based deep eutectic solvent. In these reactions, deep eutectic solvent acted as a solvent and catalyst as well. Novel Schiff bases were synthesized in high yields (65–75%) with no need for further purification, and their structures were confirmed by mass spectra, 1H and 13C NMR. Furthermore, their antioxidant activity was determined and compared to antioxidant activity of previously synthesized derivatives, thus investigating their structure–activity relationship utilizing quantitative structure-activity relationship QSAR studies. Calculation of molecular descriptors has been performed by DRAGON software. The best QSAR model (Rtr = 0.636; Rext = 0.709) obtained with three descriptors (MATS3m, Mor22u, Hy) implies that the pairs of atoms higher mass at the path length 3, three-dimensional arrangement of atoms at scattering parameter s = 21 Å1, and higher number of hydrophilic groups (-OH, -NH) enhanced antioxidant activity. Electrostatic potential surface of the most active compounds showed possible regions for donation of electrons to 1,1-diphenyl-2-picryhydrazyl (DPPH) radicals. View Full-Text
Keywords: coumarin; schiff base; deep eutectic solvents; antioxidant activity; QSAR coumarin; schiff base; deep eutectic solvents; antioxidant activity; QSAR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Molnar, M.; Komar, M.; Brahmbhatt, H.; Babić, J.; Jokić, S.; Rastija, V. Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies. Molecules 2017, 22, 1482.

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