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Synthesis, Crystal Structures, Hydrogen Bonds and Antibacterial Activity of New Quinoline Derivatives

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Abstract

Two new quinolines derivatives where crystallized from the acetylation reaction in low temperature ; between Baylis–Hillman products which had themselves been prepared from the Meth Cohn method and catalyzed by 1,4-diazabicyclo (Fatiha et al. in J Chem Crystallogr 42:989–996, 2012) octane and silicon dioxide or in pyridine and chloroform. Chemical structures have been established by spectral techniques of FTIR, 1H NMR and X-ray single crystal in low temperature. The crystal structure of (1a) crystallizes in triclinic space group P-1, a = 7.9145(12) Å, b = 9.1412(11) Å, c = 10.7286(16) Å, α = 94.760(11)°, β = 105.988(13)° , γ = 101.818(11)°, while (2a) crystallizes in orthorhombic non- centrosymmetric space group Pna21, a = 7.7237(12) Å, b = 20.2539(28) Å, c = 8.7164(12) Å, and its cohesion was found to be assured by O–H···O and C–H···O hydrogen bonds. Antimicrobial activity (in vitro) was evaluated by Gram-positive and Gram-negative bacteria. The compounds have shown good biological activity with Gram-positive bacteria (Staphylococcus aurous and Staphylococcus coagulase-negative).

Graphical Abstract

Two new Quinoline derivatives have been prepared with good products yields; these products constitute original compounds, of great interest biological activity.

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Acknowledgments

The authors acknowledge The Tassili Programme N° 15MDU940 for the financial support. In addition, A.M and T.D acknowledge the help and advice of M.R.Y.El-Hillou (Université Larbi Ben Mhidi Oum El Bouaghi).

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Authors and Affiliations

  1. Laboratoire des Structures, Propriétés et Interactions Inter Atomiques (LASPI2A), Institut des Sciences et Technologie, Université Abbés Laghrour, 40000, Khenchela, Algeria

    Tarek Djemel & Amel Messai

  2. Laboratoire des Multimatériaux et Interfaces (UMR 5615), Université Claude Bernard Lyon 1, 69622, Villeurbanne Cedex, France

    Dominique Luneau & Earwann Jeanneau

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  1. Tarek Djemel
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  2. Amel Messai
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  3. Dominique Luneau
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  4. Earwann Jeanneau
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Correspondence to Amel Messai.

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Djemel, T., Messai, A., Luneau, D. et al. Synthesis, Crystal Structures, Hydrogen Bonds and Antibacterial Activity of New Quinoline Derivatives. J Chem Crystallogr 45, 300–309 (2015). https://doi.org/10.1007/s10870-015-0595-x

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  • DOI: https://doi.org/10.1007/s10870-015-0595-x

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