Cargando…

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

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 commercial...

Descripción completa

Detalles Bibliográficos
Autores principales: Molnar, Maja, Brahmbhatt, Harshad, Rastija, Vesna, Pavić, Valentina, Komar, Mario, Karnaš, Maja, Babić, Jurislav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222480/
https://www.ncbi.nlm.nih.gov/pubmed/30060629
http://dx.doi.org/10.3390/molecules23081897
_version_ 1783369214943297536
author Molnar, Maja
Brahmbhatt, Harshad
Rastija, Vesna
Pavić, Valentina
Komar, Mario
Karnaš, Maja
Babić, Jurislav
author_facet Molnar, Maja
Brahmbhatt, Harshad
Rastija, Vesna
Pavić, Valentina
Komar, Mario
Karnaš, Maja
Babić, Jurislav
author_sort Molnar, Maja
collection PubMed
description 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; Q(2)(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.
format Online
Article
Text
id pubmed-6222480
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62224802018-11-13 Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity Molnar, Maja Brahmbhatt, Harshad Rastija, Vesna Pavić, Valentina Komar, Mario Karnaš, Maja Babić, Jurislav Molecules Article 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; Q(2)(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. MDPI 2018-07-29 /pmc/articles/PMC6222480/ /pubmed/30060629 http://dx.doi.org/10.3390/molecules23081897 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Molnar, Maja
Brahmbhatt, Harshad
Rastija, Vesna
Pavić, Valentina
Komar, Mario
Karnaš, Maja
Babić, Jurislav
Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title_full Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title_fullStr Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title_full_unstemmed Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title_short Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity
title_sort environmentally friendly approach to knoevenagel condensation of rhodanine in choline chloride: urea deep eutectic solvent and qsar studies on their antioxidant activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222480/
https://www.ncbi.nlm.nih.gov/pubmed/30060629
http://dx.doi.org/10.3390/molecules23081897
work_keys_str_mv AT molnarmaja environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT brahmbhattharshad environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT rastijavesna environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT pavicvalentina environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT komarmario environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT karnasmaja environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity
AT babicjurislav environmentallyfriendlyapproachtoknoevenagelcondensationofrhodanineincholinechlorideureadeepeutecticsolventandqsarstudiesontheirantioxidantactivity