Skip to main content
Log in

Petra, Osiris and Molinspiration (POM) together as a successful support in drug design: antibacterial activity and biopharmaceutical characterization of some azo Schiff bases

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript


Herein, we report the design and calculated molecular properties of ten existing azo Schiff bases 5ah and 7a, b. On the basis of a hypothetical antibacterial pharmacophore, the structures are designed to interact with Gram-positive and Gram-negative bacteria. The in vitro biological evaluation of these compounds allowed us to point out new potential non-nucleoside hits, with MIC values in the range of 2–8 μg/ml active against Staphylococcus aureus and Bacillus subtilis. In contrast to Gram positive strains, no activity is noted in favor of Gram negative strains (Klebsiella pneumonia, Pseudomonas aeruginosa and Escherichia coli). The antibacterial activity of these azo Schiff bases is discussed on the basis of theoretical calculations by using Petra, Osiris and Molinspiration (POM) model.

Graphical Abstract

Petra, Osiris and Molinspiration (POM) together as a successful support in drug design: antibacterial activity and biopharmaceutical characterization of some azo schiff bases.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others






  • Chohan ZH (2008) Metal-based sulfonamides: their preparation, characterization and in vitro antibacterial, antifungal & cytotoxic properties. X-ray structure of 4-[(2-hydroxybenzylidene) amino] benzenesulfonamide. J Enzy Inhib Med Chem 23:120–130

    Article  CAS  Google Scholar 

  • Chohan ZH, Shad HA, Tahir MN (2009) 4-[(E)-(5-Chloro-2-hydroxybenzylidene)amino]benzenesulfonamide. Acta Cryst Sect E Struct O-57. doi:10.1107/S1600536808040853

  • Ehrlich P (1909) Present status of chemotheraphy that carries (phoros) the essential features responsible for a drug’s (pharmacon’s) biological activity. Ber Dtsch Chem Ges 42:17–47

    Article  CAS  Google Scholar 

  • Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area (PSA) as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714–3717

    Article  PubMed  CAS  Google Scholar 

  • Gund P (1977) Three dimensional pharmacophoric pattern searching in a molecule that is recognized at a receptor site and is responsible for that molecule’s biological activity. Prog Mol Subcell Biol 5:117–143

    Article  CAS  Google Scholar 

  • Güner OF (ed) (2000) Pharmacophore perception, development, and use in drug design, ISBN 0-9636817-6-1. (

  • Jarrahpour A, Motamedifar M, Pakshir K, Hadi N, Zarei M (2004) Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities. Molecules 9:815–824

    Article  PubMed  CAS  Google Scholar 

  • Langer T, Hoffmann RD (2006) Pharmacophores and pharmacophore searches, ISBN 3-527-31250-1

  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3–26

    Article  PubMed  CAS  Google Scholar 

  • Sheikh J, Parvez A, Juneja H, Ingle V, Chohan Z, Yousoufi M, Ben Hadd T (2011) Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones. Eur J Med Chem 46(4):1390–1399

    Article  PubMed  CAS  Google Scholar 

  • Touzani R, Ben Hadda T, Elkadiri S, Ramdani A, Maury O, Le Bozec H, Toupet L, Dixneuf PH (2001) Solution, solid state structure and nuorescence studies of 2,3-functionalized quinoxalines: evidence for a p-delocalized keto-enamine form with (N.H–O) intramolecular hydrogen bonds. New J Chem 25:391–395

    Article  CAS  Google Scholar 

  • Waring MJ, Ben Hadda T, Kotchevar AT, Ramdani A, Touzani R, Elkadiri S, Hakkou A, Bouakka M, Ellis T (2002) 2,3-Bifunctionalized quinoxalines: synthesis, DNA interactions and evaluation of anticancer, anti-tuberculosis and antifungal activity. Molecules 7:641–656

    Article  CAS  Google Scholar 

Download references


The authors thank the Shiraz University Research Council for financial support (Grant No. 87-GR-SC-23). We would like to thank the ACTELION; the Biopharmaceutical Company of Swiss, for the on-line molecular properties calculations.

Author information

Authors and Affiliations


Corresponding authors

Correspondence to Taibi Ben Hadda or Javed Sheikh.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jarrahpour, A., Fathi, J., Mimouni, M. et al. Petra, Osiris and Molinspiration (POM) together as a successful support in drug design: antibacterial activity and biopharmaceutical characterization of some azo Schiff bases. Med Chem Res 21, 1984–1990 (2012).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: