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Synthesis of 3-ferrocenylaniline: DNA interaction, antibacterial, and antifungal activity

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Abstract

Bioactive 3-ferrocenylaniline [(η5-C5H4)2Fe{C6H5NH2}] has been successfully synthesized and characterized by means of various physico-analytical techniques such as FTIR and multinuclear (1H and 13C) NMR spectroscopy along with melting point and elemental analysis. The interaction of the 3-ferrocenylaniline with DNA has been investigated by spectroscopic and viscometric measurements. The interaction of compound with DNA is presumably occurring via hydrogen bonding. Viscosity measurement of the compound has proved to change in length and is regarded as the least ambiguous and the most critical test of binding model in solution. The antibacterial activity was carried out using Gram-positive bacteria (Staphylococcus aureus, Micrococcus luteus) and Gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae) and found to be selective and effective against Gram-positive bacteria. In vitro antifungal activity was determined against the fungal species (Aspergillus niger and Aspergillus flavus) and demonstrated significant activity.

Graphical Abstract

Compound 1 was synthesized from ferrocene and 3-nitroaniline in the presence of sodium nitrite/hydrochloric acid and the resulting product was reduced to 3-ferrocenyl aniline. The compound was characterized by IR, multinuclear (1H and 13C) NMR, and elemental analysis. DNA interaction studies were examined by spectroscopic and viscosity measurements. Antibacterial and antifungal activities are also tested.

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Acknowledgments

Authors highly acknowledge the Department of Microbiology, Quaid-I-Azam University and Higher Education Commission Islamabad, Pakistan, for their support.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Shafqat Ali, Amin Badshah, Ataf Ali Ataf,  Imtiaz-ud-Din & Bhajan Lal

  2. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Khalid Mohammed Khan

  3. Department of Chemistry, University of Malakand, Chakdara, Pakistan

    Ataf Ali Ataf

Authors
  1. Shafqat Ali
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  2. Amin Badshah
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  3. Ataf Ali Ataf
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  4. Imtiaz-ud-Din
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  5. Bhajan Lal
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  6. Khalid Mohammed Khan
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Correspondence to Khalid Mohammed Khan.

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Ali, S., Badshah, A., Ataf, A.A. et al. Synthesis of 3-ferrocenylaniline: DNA interaction, antibacterial, and antifungal activity. Med Chem Res 22, 3154–3159 (2013). https://doi.org/10.1007/s00044-012-0311-8

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  • DOI: https://doi.org/10.1007/s00044-012-0311-8

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