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DOI: 10.1055/s-0040-1719869
Synthesis and Molecular Docking Studies of N,N-Dimethyl Arylpyranopyrimidinedione Derivatives
The authors acknowledge funding from the Department of Science and Technology through the Fund for Improvement of S&T Infrastructure in Universities and Higher Educational Institutions Program (DST-FIST; SR/FST/CS-II/2018/64).
Abstract
The synthesis of N,N-dimethyl arylpyranopyrimidinedione derivatives from aromatic aldehydes, N-methyl-1-(methylthio)-2-nitroethamine (NMSM) and 1,3-dimethyl barbituric acid, in the presence of piperidine as a catalyst, is reported. The reaction mechanism involves a Knoevenagel condensation, followed by Michael addition and intramolecular O-cyclization reaction sequence. The synthesized compounds were docked with human kinesin Eg5 protein to calculate binding energy, inhibition constant and H-bond interaction. All the compounds show good binding affinity towards the protein, with significant docking score.
Keywords
N,N-dimethyl arylpyranopyrimidinedione - Knoevenagel condensation - Michael addition - O-cyclization - docking studiesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719869. 1H, 13C and Dept-135 NMR and HR-MS spectroscopic data of 4a–k and docking images are included.
- Supporting Information
Publication History
Received: 05 October 2021
Accepted after revision: 15 December 2021
Article published online:
10 January 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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