Pharmaceutical Chemistry Journal

, Volume 46, Issue 6, pp 381–385 | Cite as

Synthesis and biological evaluation of new bis-indolyl (3-O-benzyl-1,2-O-isopropylidenexylopentadialdose-α-D-glucofuranose)

  • M. Shankar
  • A. Balasubramaniam
  • N. L. Gowrishankar
  • S. Mahendran

3-O-benzyl-1,2-O-isopropylidene-xylopentadialdose has emerged as structurally new antibacterial and anti-inflammatory agent. Therefore, various substituted bis-indolyl-(3-O-benzyl-1,2-O-isopropylidene-xylopentadialdose glucofuranose) derivatives were synthesized by addition of substituted xylopentadialdose with various substituted indoles. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectroscopy techniques. All the synthesised compounds showed maximum zone of inhibition againt both Gram-positive and Gram-negative organisms. In the anti-inflammatory activity test, three compounds (1, 3 and 5) produced significant activity in a dose-dependent manner.

Key words

3-O-benzyl-1,2-O-isopropylidene-xylopentadialdose antibacterial activity anti-inflammatory activity 


  1. 1.
    M. J. Kershaw, D. A. Leigh, J. Antimicrob. Chemother., 311 – 315 (1975).Google Scholar
  2. 2.
    G. Imperato, E. Eibler, J. Neidermarer, et al., Chem. Commun., 1170 (2005); K. Manabe and S. Kobayashi, Chem. Eur. J, No. 8, 4094 – 4101 (2008).Google Scholar
  3. 3.
    C. J. Li and T. H. Cahn, Organic Reactions in Aqueous Media, John Wiley & Sons, New York (1997).Google Scholar
  4. 4.
    A. E. Thomas, O. L. Kenneth, Y. C. Wenying, et al., J. Org. Chem., 67, 7884 (2002).CrossRefGoogle Scholar
  5. 5.
    J. S. Yadav, B. V. Subba Reddy, Ch. V. S. R. Murthy, et al. Synthesis, 783 (2001).Google Scholar
  6. 6.
    E. A. Fehnel, J. Heterocycl. Chem., 4, 565 (1967).CrossRefGoogle Scholar
  7. 7.
    V. P. Veerapur, P. Bansal, et al., Bioorg. Med. Chem., 14, 7113 – 7120 (2006).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • M. Shankar
    • 1
  • A. Balasubramaniam
    • 2
  • N. L. Gowrishankar
    • 3
  • S. Mahendran
    • 4
  1. 1.Department of Pharmaceutical ChemistrySwami Vivekanandha Institute of Pharmaceutical SciencesVangapallyIndia
  2. 2.Department of Pharmaceutical ChemistryJ. K. K. Munirajah Medical Research Foundation College of PharmacyKomarapalayamIndia
  3. 3.Department of PharmacognosySwami Vivekanandha Institute of Pharmaceutical SciencesVangapallyIndia
  4. 4.Department of Pharmaceutical ChemistryJ. S. S. College of PharmacyRocklandsIndia

Personalised recommendations