Medicinal Chemistry Research

, Volume 23, Issue 3, pp 1248–1256 | Cite as

Novel derivatives of 5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazine-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid: their synthesis, antimicrobial, antifungal, and urease inhibitory studies

  • M. Saeed Arayne
  • Najma Sultana
  • Somia Gul
  • Ajmal Khan
Original Research
First Online:
Received:
Accepted:

Abstract

Sparfloxacin (SPFX) or 5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazine-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid is an orally active synthetic, broad spectrum third generation quinolone, with excellent activity against Gram-positive bacteria with selectivity against anaerobes and atypical pathogens. Three derivatives of SPFX (2, 3, and 4) were synthesized by reacting different aromatic carboxylic acids with SPFX (1). Chemistry involved the formation of amide between reacting species through nucleophilic substitution reactions. The synthesized derivatives were then structurally characterized by IR, NMR, and mass spectroscopic techniques. The antimicrobial activities of these derivatives were evaluated against four Gram-positive, seven Gram-negative bacteria, and six fungi, using SPFX as a reference. Statistical analysis revealed these derivatives as active antimicrobial agents, and 2 was more potent antimicrobial agents than the parent drug as well other fluoroquinolones. Compounds 3 and 4 showed a significant activity against Fusarium solani. Moreover, these three derivatives were evaluated for inhibitory activities against enzyme urease, carbonic anhydrase II, and α-chymotrypsin. Results showed their selectivity against urease enzyme. Based on their nontoxic behavior, these derivatives may be potential agents for further studies.

Keywords

Sparfloxacin Derivatives Antimicrobial activities Urease Enzyme inhibition 
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Notes

Acknowledgments

Mrs. Somia Gul acknowledges the financial support of Higher Education Commission Pakistan (Indigenous 5000 Ph.D Fellowship Program) to complete her Ph.D.

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • M. Saeed Arayne
    • 1
  • Najma Sultana
    • 2
  • Somia Gul
    • 2
  • Ajmal Khan
    • 3
  1. 1.Department of ChemistryUniversity of KarachiKarachiPakistan
  2. 2.Research Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, Faculty of PharmacyUniversity of KarachiKarachiPakistan
  3. 3.H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological SciencesUniversity of KarachiKarachiPakistan

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