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Arabian Journal for Science and Engineering
Published in: Arabian Journal for Science and Engineering 6/2021

16-11-2020 | Research Article-Chemistry

Synthesis, Characterization, Biocomputational Modeling and Antibacterial Study of Novel Pyran Based on 8-Hydroxyquinoline

Authors: M. Rbaa, A. Hichar, P. Dohare, El H. Anouar, Y. Lakhrissi, B. Lakhrissi, M. Berredjem, F. Almalki, V. Rastija, M. Rajabi, T. Ben Hadda, A. Zarrouk

Published in: Arabian Journal for Science and Engineering | Issue 6/2021

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Abstract

In this work, we report the synthesis of a new family of organic compounds based on 8-hydroxyquinoline using a simple and efficient method. The synthesized 8-hydroxyquinoline derivatives were characterized by analysis of 1H and 13C NMR, FT-IR spectral data and elemental analysis (EA). Their antibacterial activity is tested against Gram-positive strains [S. aureus (ATCC29213), V. parahaemolyticus (ATCC17802)] and Gram negative [E. coli (ATCC35218), P. aeruginosa (ATCC27853)] by the use of the agar diffusion technique. The obtained results showed that the synthesized 8-hydroxyquinoline derivatives have a potent antibacterial activity against the tested strains compared to Norfloxacin as a standard antibiotic. The results also reveal the effectiveness of these compounds at low concentrations, with a MIC of 1.00 μg/ml for compound 4a. Their antibacterial activity has also been optimized by bioinformatics studies (POM analyses). The experimental results are in relatively good agreement with the corresponding theoretical ones.
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Appendix
Available only for authorised users
Literature
1.
Cruz, A.F.; Ishii, T.: Arbuscular mycorrhizal fungal spores host bacteria that affect nutrient biodynamics and biocontrol of soilborne plant pathogens. Biol. Open 1, 52–57 (2012)CrossRef
2.
Rbaa, M.; Hichar, A.; Bazdi, O.; Lakhrissi, Y.; Ounine, K.; Lakhrissi, B.: Synthesis, characterization, and in vitro antimicrobial investigation of novel pyran derivatives based on 8-hydroxyquinoline. Beni-Suef Univ. J. Basic Appl. Sci. 8, 8 (2019)CrossRef
3.
Mallikarjuna, N.M.; Keshavayya, J.: Synthesis, spectroscopic characterization and pharmacological studies on novel sulfamethaxazole based azo dyes. J. King Saud Univ. Sci. 32, 251–259 (2020)CrossRef
4.
Rbaa, M.; Abousalem, A.S.; Rouifi, Z.; Benkaddour, R.; Dohare, P.; Lakhrissi, M.; Zarrouk, A.: Synthesis, antibacterial study and corrosion inhibition potential of newly synthesis oxathiolan and triazole derivatives of 8-hydroxyquinoline: experimental and theoretical approach. Surf. Interfaces. 19, 100468 (2020)CrossRef
5.
Rbaa, M.; Jabli, S.; Lakhrissi, Y.; Ouhssine, M.; Almalki, F.; Ben Hadda, T.; Lakhrissi, B.: Synthesis, antibacterial properties and bioinformatics computational analyses of novel 8-hydroxyquinoline derivatives. Heliyon. 5, e02689 (2019)CrossRef
6.
Zou, Y.L.; Li, H.Y.; Zhou, W.; Cui, X.G.; Zou, G.H.; Shen, G.Z.: Introduction of the antibacterial drugs norfloxacin and Ciprofloxacin into a polyoxometalate structure: synthesis, characterization, and antibacterial activity. J. Mol. Struct. 1205, 127584 (2020)CrossRef
7.
Matsui, T.; Yamane, J.; Mogi, N.; Yamaguchi, H.; Takemoto, H.; Yao, M.; Tanaka, I.: Structural reorganization of the bacterial cell-division protein FtsZ from Staphylococcus aureus. Acta Crystallogr. D Biol. Crystallogr. 68, 1175–1188 (2012)CrossRef
8.
Andreu, J.M.; Schaffner-Barbero, C.; Huecas, S.; Alonso, D.; Lopez-Rodriguez, M.L.; Ruiz-Avila, L.B.; Martín-Galiano, A.J.: The antibacterial cell division inhibitor PC190723 is an FtsZ polymer-stabilizing agent that induces filament assembly and condensation. J. Biol. Chem. 285(19), 14239–14246 (2010)CrossRef
9.
Grimme, S.: A simplified Tamm-Dancoff density functional approach for the electronic excitation spectra of very large molecules. J. Chem. Phys. 138, 244104 (2013)CrossRef
10.
Andersson, M.P.: Uvdal, P: new scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-ζ basis set 6-311 + G (d, p). J. Phys. Chem. A. 109, 2937–2941 (2005)CrossRef
11.
Wolinski, K.; Hinton, J.F.; Pulay, P.: Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 112, 8251–8260 (1990)CrossRef
12.
Das, U.; Das, S.; Bandy, B.; Stables, J.P.; Dimmock, J.R.: N-Aroyl-3, 5-bis (benzylidene)-4-piperidones: a novel class of antimycobacterial agents. Bioorg. Med. Chem. 16, 3602–3607 (2008)CrossRef
13.
Mehta, P.D.; Sengar, N.P.S.; Pathak, A.K.: 2-Azetidinone–a new profile of various pharmacological activities. Eur. J. Med. Chem. 45, 5541–5560 (2010)CrossRef
14.
Ali, A.T.; Mosa, M.N.; Alshaheen, Z.G.; Muhammad-Ali, M.A.: Synthesis, characterization and antibacterial evaluation of oxoazetidin benzene sulfonamide derivatives as a hybrid antimicrobial agents. Syst. Rev. Pharm. 11, 487–494 (2020)
15.
Ben Hadda, T.; Srivastava, S.; Das, B.; Salgado-Zamora, H.; Shaheen, U.; Bader, A.; Naseer, M.M.: POM analyses of antimicrobial activity of some 2, 3-armed 4, 5, 6, 7-tetrahydro-1-benzothiophenes: favourable and unfavourable physico-chemical parameters in design of antibacterial and mycolytic agents. Med. Chem. Res. 23, 995–1003 (2014)CrossRef
16.
Parvez, A.; Jyotsna, M.; Youssoufi, M.H.; Ben Hadda, T.: Bioinformatic prediction and experimental verification of antibacterial potential of some monocyclic β-lactams containing two synergetic buried antibacterial pharmacophore sites (Part II). Phosphorus Sulfur Silicon Relat. Elem. 185, 1500–1510 (2010)CrossRef
17.
Sheikh, J.; Parvez, A.; Juneja, H.; Ingle, V.; Chohan, Z.; Youssoufi, M.; Ben Hadda, T.: Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones. Eur. J. Med. Chem. 46(4), 1390–1399 (2011)CrossRef
18.
Jarrahpour, A.; Fathi, J.; Mimouni, M.; Ben Hadda, T.; Sheikh, J.; Chohan, Z.; Parvez, A.: Petra, osiris and molinspiration (POM) together as a successful support in drug design: antibacterial activity and biopharmaceutical characterization of some azo Schiff bases. Med. Chem. Res. 21(8), 1984–1990 (2012)CrossRef
19.
Lautre, H.K.; Singh, R.; Patil, K.; Ben Hadda, T.; Youssouffi, H.; Bose, P.; Prasad, C.: Synthesis and biological evaluation of metal complexes derived from 3-methyl-n-hydroxybenzamidine as potent inhibitors of thymidylate kinase from mycobacterium tuberculosis. World J. Pharm. Pharm. Sci. 3, 1564–1583 (2014)
Metadata
Title
Synthesis, Characterization, Biocomputational Modeling and Antibacterial Study of Novel Pyran Based on 8-Hydroxyquinoline
Authors
M. Rbaa
A. Hichar
P. Dohare
El H. Anouar
Y. Lakhrissi
B. Lakhrissi
M. Berredjem
F. Almalki
V. Rastija
M. Rajabi
T. Ben Hadda
A. Zarrouk
Publication date
16-11-2020
Publisher
Springer Berlin Heidelberg
Published in
Arabian Journal for Science and Engineering / Issue 6/2021
Print ISSN: 2193-567X
Electronic ISSN: 2191-4281
DOI
https://doi.org/10.1007/s13369-020-05089-y

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