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Synthesis, characterization, and biological evaluation of new oxime-phosphazenes

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An Erratum to this article was published on 11 May 2013

Abstract

Hexachlorocylotriphosphazene (1) was reacted with 4-hydroxy-3-methoxybenzaldehyde to give hexakis[(4-formyl-2-methoxy)phenoxy]cyclotriphosphazene (2). Hexakis[(4-(hydroxyimino)2-methoxy)phenoxy]cyclotriphosphazene (3) was synthesized by reaction of 2 with hydroxlamine hydrochloride in pyridine. Compound 3 was reacted with benzyl chloride, acetyl chloride, allyl bromide, benzoyl chloride, propanoyl chloride, 4-methoxybenzoyl chloride, 2-chlorobenzoyl chloride, chloroacetyl chloride, methyl iodide, and thiophene-2-carbonyl chloride. From these reactions, full or partially substituted compounds were obtained, usually in high yields. Pure or defined products could not be obtained from reaction of 3 with methacryloyl chloride and O-acetylsalicyloyl chloride. The structures of the compounds were determined by elemental analysis, and IR, 1H, 13C, and 31P NMR spectroscopy. The synthesized compounds were screened for in-vitro antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Enterococcus faecalis), two gram-negative bacteria (Escherichia coli and Klebsiella pneumonia), and fungal strains (Aspergillus niger, and Candida albicans) by the agar well diffusion method. Few compounds had significant activity against both Gram-positive and Gram-negative bacteria. None of the compounds had antifungal activity except compounds 7 and 9, which had moderate activity.

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Scheme 1
Scheme 2
Fig. 1
Fig. 2

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Acknowledgments

The authors are grateful to the Firat University Research Fund for financial support of this work (project no: FF.11.04).

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Authors and Affiliations

  1. Chemistry Department, Science Faculty, Firat University, 23169, Elazig, Turkey

    Kenan Koran & Furkan Ozen

  2. Biochemistry Department, Science Faculty, Adiyaman University, 02040, Adiyaman, Turkey

    Ahmet Ozkaya

  3. Science Education Department, Education Faculty, Firat University, 23169, Elazig, Turkey

    Erol Cil

  4. Science Education Department, Education Faculty, Yildiz Technical University, Istanbul, Turkey

    Mustafa Arslan

Authors
  1. Kenan Koran
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  2. Ahmet Ozkaya
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  3. Furkan Ozen
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  4. Erol Cil
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Correspondence to Erol Cil.

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Koran, K., Ozkaya, A., Ozen, F. et al. Synthesis, characterization, and biological evaluation of new oxime-phosphazenes. Res Chem Intermed 39, 1109–1124 (2013). https://doi.org/10.1007/s11164-012-0670-2

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