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Could X-Ray Analysis Explain for the Differing Antimicrobial and Antioxidant Activity of Two 2-Arylamino-3-Nitro-Coumarins?

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Abstract

X-Ray analyses of 4-(naphthalen-1-ylamino)-3-nitro-chromen-2-one and 3-nitro-4-phenylamino-chromen-2-one showed that the mentioned compounds crystallize in the space groups P1- (triclinic crystal system; unit cell parameters: a = 8.087(2) Å, b = 9.241(3) Å, c = 10.911(3) Å, α = 93.77(3)°, β = 102.51(3)°, γ = 106.44(2)°, V = 756.4(4) Å3 and Z = 2) and P212121 (orthorhombic crystal system; unit cell parameters: a = 4.9274(9) Å, b = 14.725(3) Å, c = 17.866(4) Å, α = β = γ = 90°, V = 1296.3(5) Å3 and Z = 4), respectively. The analyses of crystal structures and gas phase conformations, inferred from single X-ray crystallographic and molecular modeling experiments, respectively, showed that the changes in π delocalization of the farmacoactive formal 3-amino-2-nitro-acrylic acid derivatives might explain the observed significant difference of the antimicrobial and antioxidant activities and spectral properties of two 4-arylamino-3-nitro-coumarin derivatives.

Graphical Abstract

In this work we considered the possibility that the changes in the π-delocalization of the pharmacoactive 4-(naphthalene-1-ylamino)- and 4-phenylamino-3-nitro-chromen-2-ones, inferred from X-ray analysis, might explain significant alterations of the antioxidant and antimicrobial activities (and spectral ones) of two coumarin derivatives.

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Acknowledgments

The authors acknowledge the Ministry of Science and Technological Development of Serbia for financial support (project number 172061).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000, Niš, Serbia

    Niko S. Radulović & Polina D. Blagojević

  2. VINČA Institute of Nuclear Science, Laboratory of Theoretical Physics and Condensed Matter Physics, 522, 11001, Belgrade, Serbia

    Goran A. Bogdanović

  3. Department of Chemistry, Faculty of Science and Mathematics, University of Priština, Priština, Serbia

    Vidosav S. Dekić

  4. Department of Chemistry, Faculty of Science and Mathematics, University of Kragujevac, R. Domanovića 12, 34000, Kragujevac, Serbia

    Rastko D. Vukićević

Authors
  1. Niko S. Radulović
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  2. Goran A. Bogdanović
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  3. Polina D. Blagojević
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  4. Vidosav S. Dekić
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  5. Rastko D. Vukićević
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Correspondence to Niko S. Radulović.

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Radulović, N.S., Bogdanović, G.A., Blagojević, P.D. et al. Could X-Ray Analysis Explain for the Differing Antimicrobial and Antioxidant Activity of Two 2-Arylamino-3-Nitro-Coumarins?. J Chem Crystallogr 41, 545–551 (2011). https://doi.org/10.1007/s10870-010-9918-0

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  • DOI: https://doi.org/10.1007/s10870-010-9918-0

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