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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Synthesis and Molecular Docking of New 1,2,3-triazole Carbohydrates with COVID-19 Proteins

Author(s): Naoufel Ben Hamadi*, Ahlem Guesmi, Faisal K. Algathami, Lotfi Khezami, Wided Nouira and Wesam Abd El-Fattah

Volume 20, Issue 2, 2023

Published on: 08 September, 2022

Page: [238 - 245] Pages: 8

DOI: 10.2174/1570179419666220414095602

Price: $65

Abstract

Aims: We have established this paper to recommend a novel way for the preparation of carbohydrates encompassing a 1,2,3-triazole motif that was prepared using an efficient click chemistry synthesis.

Background: The SARS-CoV-2 coronavirus epidemic continues to spread at a fast rate worldwide. The main protease (Mpro) is useful target for anti-COVID-19 agents. Triazoles are frequently found in many bioactive products, such as coronavirus inhibitors.

Objective: Click reactions are facilitated via the activation of copper nanoparticles, different substrates have been tested using this adopted procedure given in all cases, in high yields and purity. Other interesting comparative docking analyses will be the focus of this article. Calculations of quantitative structure-activity relationships will be studied.

Methods: Copper nanoparticles were produced by the reaction of cupric acetate monohydrate with oleylamine and oleic acid. To a solution, 5-(azidomethyl)-2,2,7,7-tetramethyltetrahydro-5Hbis([ 1,3]dioxolo)[4,5-b:4',5'-d]pyran 2 (200 mg, 0.72 mmol, 1 eq.) in toluene (15 mL) was added into a mixture of N-(prop-2-yn-1-yl)benzamide derivatives 1a-d (1.5 eq.) and copper nanoparticles (0.57 mg, 0.036 mmol, 0.05 eq.).

Results: A novel series of 1,2,3-triazole carbohydrate skeletons were modeled and efficiently synthesized. Based on the observations, virtual screening using molecular docking was performed to identify novel compounds that can bind with the protein structures of COVID-19 (PDB ID: 6LU7 and 6W41). We believed that the 1,2,3-triazole carbohydrate derivatives could aid in COVID-19 drug discovery.

Conclusion: The formations of targeted triazoles were confirmed by different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, and CHN analyses). The docking scores of the newly synthesized triazole are attributed to the presence of hydrogen bonds together with many interactions between the ligands and the active amino acid residue of the receptor. The comparison of the interactions of the drugs, remdesivir and triazole, in the largest pocket of 6W41 and 6LU7 is also presented.

Keywords: Click chemistry, triazole, carbohydrates, remdesivir, Covid-19, docking.

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[1]
Bertram, L.; Tanzi, R.E. Thirty years of Alzheimer’s disease genetics: The implications of systematic meta-analyses. Nat. Rev. Neurosci., 2008, 9(10), 768-778.
[http://dx.doi.org/10.1038/nrn2494] [PMID: 18802446]
[2]
Boppana, K.; Dubey, P.K.; Jagarlapudi, S.A.R.P.; Vadivelan, S.; Rambabu, G. Knowledge based identification of MAO-B selective inhibitors using pharmacophore and structure based virtual screening models. Eur. J. Med. Chem., 2009, 44(9), 3584-3590.
[http://dx.doi.org/10.1016/j.ejmech.2009.02.031] [PMID: 19321235]
[3]
Hughes, J.P.; Rees, S.; Kalindjian, S.B.; Philpott, K.L. Principles of early drug discovery. Br. J. Pharmacol., 2011, 162(6), 1239-1249.
[http://dx.doi.org/10.1111/j.1476-5381.2010.01127.x] [PMID: 21091654]
[4]
Hajlaoui, K.; Guesmi, A.; Ben Hamadi, N.; Msaddek, M. One-pot synthesis of new triazole-sucrose derivatives via click chemistry and evaluation of their antitubercular activity. Heterocycl. Commun., 2016, 22, 239-242.
[http://dx.doi.org/10.1515/hc-2016-0028]
[5]
Cabrele, C.; Reiser, O. The modern face of synthetic heterocyclic chemistry. J. Org. Chem., 2016, 81(21), 10109-10125.
[http://dx.doi.org/10.1021/acs.joc.6b02034] [PMID: 27680573]
[6]
Song, X.G.; Ren, Y.Y.; Zhu, S.F.; Zhou, Q.L. Enantioselective copper-catalyzed intramolecular N−H bond insertion: Synthesis of chiral 2-carboxytetrahydroquinolines. Adv. Synth. Catal., 2016, 358, 2366-2370.
[http://dx.doi.org/10.1002/adsc.201600390]
[7]
Ben Hamadi, N.; Msaddek, M. Synthesis and reactivity of N-sugar-maleimides: An access to novel highly substituted enantiopure pyrazolines. Tetrahedron Asymmetry, 2012, 23, 1689-1693.
[http://dx.doi.org/10.1016/j.tetasy.2012.11.005]
[8]
Ben Hamadi, N.; Msaddek, M. 1,3-dipolar cycloadditions of arylnitrile oxides and 2-diazopropane with 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives. C. R. Chim., 201114, 891-895.
[http://dx.doi.org/10.1016/j.crci.2011.02.005]
[9]
Vitaku, E.; Smith, D.T.; Njardarson, J.T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem., 2014, 57(24), 10257-10274.
[http://dx.doi.org/10.1021/jm501100b] [PMID: 25255204]
[10]
Vo, C.V.T.; Bode, J.W. Synthesis of saturated N-heterocycles. J. Org. Chem., 2014, 79(7), 2809-2815.
[http://dx.doi.org/10.1021/jo5001252] [PMID: 24617516]
[11]
Estévez, V.; Villacampa, M.; Menéndez, J.C. Recent advances in the synthesis of pyrroles by multicomponent reactions. Chem. Soc. Rev., 2014, 43(13), 4633-4657.
[http://dx.doi.org/10.1039/C3CS60015G] [PMID: 24676061]
[12]
Joule, J.A.; Mills, K. Heterocyclic Chemistry; Blackwell: Oxford, UK, 2000.
[13]
Mengist, H.M.; Dilnessa, T.; Jin, T. Structural basis of potential inhibitors targeting SARS-CoV-2 main protease. Front Chem., 2021, 9, 622898.
[http://dx.doi.org/10.3389/fchem.2021.622898] [PMID: 33889562]
[14]
Word health organization director-general's opening remarks at the media briefing on COVID-19., Available from: https://www.who.int/director-general/speeches/detail/who-director-general-s-opening-remarks-at-the-media-briefing-on-covid-19-11-march-2020 (Accessed on March 11, 2020).
[15]
Word Health Organization. Available from: https://www.gavi.org/ 2021
[16]
Nicola, M.; Alsafi, Z.; Sohrabi, C.; Kerwan, A.; Al-Jabir, A.; Iosifidis, C.; Agha, M.; Agha, R. The socio-economic implications of the coronavirus pandemic (COVID-19): A review. Int. J. Surg., 2020, 78, 185-193.
[http://dx.doi.org/10.1016/j.ijsu.2020.04.018] [PMID: 32305533]
[17]
Lane, H.C.; Al, N. A trial of lopinavir-ritonavir in adults hospitalized with severe Covid-19. Engl. J. Med, 2020, 383, 1813-1826.
[18]
Yao-Wu, H.; Chang-Zhi, D.; Jiang-Yu, Z.; Lin-Lin, M.; Yu-Huan, L.; Haji Akber, A. 1,2,3-Triazole-containing derivatives of rupestonic acid: Click-chemical synthesis and antiviral activities against influenza viruses. Eur. J. Med. Chem., 2014, 76, 245-255.
[http://dx.doi.org/10.1016/j.ejmech.2014.02.029] [PMID: 24583605]
[19]
Zhao, J.; Aisa, H.A. Synthesis and anti-influenza activity of aminoalkyl rupestonates. Bioorg. Med. Chem. Lett., 2012, 22(6), 2321-2325.
[http://dx.doi.org/10.1016/j.bmcl.2012.01.056] [PMID: 22341943]
[20]
Seck, I.; Nguemo, F. Triazole, imidazole, and thiazole-based compounds as potential agents against coronavirus. Results Chem., 2021, 3, 100132.
[http://dx.doi.org/10.1016/j.rechem.2021.100132] [PMID: 33907666]
[21]
Satyaki, C.; Neeraj, K.; Hitesh, S.; Nisha, Y.; Vivek, M. Click triazole as a linker for drug repurposing against SARs-CoV-2: A greener approach in race to find COVID-19 therapeutic. Curr. Res.Green Sustainable Chem., 2021, 4, 100064.
[22]
Giorgio, M.; Claudia, L.B.; Giorgio, M.; Nadia, S.; Alessandro, P. Cu/Cu-oxide nanoparticles as catalyst in the “click” azide-alkyne cycloaddition. New J. Chem., 2006, 30, 1137-1139.
[http://dx.doi.org/10.1039/B604297J]
[23]
Hajlaoui, K.; Ben Hamadi, N.; Msaddek, M. Copper nanoparticles cycloaddition of terminal acetylenes with carbohydrate azide. Catal. Lett., 2015, 145, 1246-1250.
[http://dx.doi.org/10.1007/s10562-015-1521-8]
[24]
Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed., 2002, 41(14), 2596-2599.
[http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4] [PMID: 12203546]

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