Subscribe to RSS
Download PDF
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. The Author(s). 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/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Muthusamy S, Ramkumar R. Synlett 2015; 2156
- 2 Khan S, Rahman H, Khan MM. RSC Adv. 2019; 9: 4477
- 3 Nagaraja O, Bodke YD, Pushpavathi I, Kumar SR. Heliyon 2020; 6: e04245
- 4a Xu K, Yuan XL, Li C. Marine Drugs 2020; 18: 54
- 4b Kerru N, Gummidi L, Maddila S, Jonnalagadda G. Molecules 2020; 25: 1909
- 4c Ziarani GM, Faramarzi S, Asadi S, Badiei R, Bazl A, Amanlou M. J. Pharm. Sci. 2013; 21: 3
- 4d Thibert J, Farine JP, Cortot J, Ferveur JF. PloS one 2016; e0151451
- 5 Song S, Huang M, Li W, Zhu X, Wan Y. Tetrahedron 2015; 71: 451
- 6 Kumar A, Shukla RD. Green Chem. 2015; 17: 848
- 7 Prabhakaran S, Velmathi S. ChemistrySelect 2021; 6: 8696
- 8 Saigal, Khan S, Rahman H, Shafiullah, Khan MM. RSC Adv. 2019; 9: 14477
- 9 Brahmachari G. ACS Sustainable Chem. Eng. 2015; 3: 2058
- 10 Brahmachari G, Banerjee B. ACS Sustainable Chem. Eng. 2014; 2: 411
- 11 Song S, Huang M, Li W, Zhu X, Wan Y. Tetrahedron 2015; 71: 451
- 12a Hassan EM, Belal F. J. Pharm. Biomed. Anal. 2002; 27: 31
- 12b Ashiru DA, Patel R, Basit AW. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2007; 86: 235
- 13 Shehab WS, El-Farargy AF, Abdelhamid AO, Aziz MA. Synth. Commun. 2019; 49: 3560
- 14 Nagaraju P, Reddy PN, Padmaja P, Ugale VG. Lett. Org. Chem. 2020; 17: 951
- 15a Ouf NH, Amr AE. G. E, Sakran MI. Med. Chem. Res. 2015; 24: 1514
- 15b Das P, Chaudhuri T, Mukhopadhyay C. ACS Comb. Sci. 2014; 16: 606
- 16a Emami S, Ghanbarimasir Z. Eur. J. Med. Chem. 2015; 93: 539
- 16b Harel D, Schepmann D, Prinz H, Brun R, Schmidt TJ, Wünsch B. J. Med. Chem. 2013; 56: 7442
- 17a Reheim MA, Hafiz IS, Elian MA. Curr. Org. Synth. 2020; 17: 548
- 17b Lin ZL, Zhang JM, Gao Y. J. Heterocycl. Chem. 2017; 54: 596
- 18 Gawande MB, Bonifacio VD. B, Luque R, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
- 19a Brahmachari G, Nayek N. ACS Omega 2017; 2: 5025
- 19b
Singh MS,
Chowdhury S.
RSC Adv. 2012; 2: 4547
MissingFormLabel
- 20a Kalaria PN, Karad SC, Raval DK. Eur. J. Med. Chem. 2018; 158: 917
- 20b Valentin JE, Freytes DO, Grasman JM, Pesyna C, Freund J, Gilbert TW, Badylak SF. J. Biomed. Mater. Res., Part A 2009; 91: 1010
- 21 Cahu J, Olichon A, Hentrich C, Schek H, Drinjakovic J, Zhang C, Surrey T. PloS one 2008; e3936
- 22 Kull FJ, Sablin EP, Lau R, Fletterick RJ, Vale RD. Nature 1996; 380: 550
- 23 Ferenz NP, Gable A, Wadsworth P. Semin. Cell Dev. Biol. 2010; 21: 255