Shipra Baluja, Sumitra Chanda


In this study, the series of novel azomethines were synthesized from methyl salicylate and their structural determination was done by IR, NMR and mass spectral data. The screening of these synthesized compounds were done against some Gram positive and Gram negative bacteria in DMF and DMSO solvents by agar disc method. It is observed that solvent and compound structure both affect the inhibition. DMF is found to be good solvent in the present study. Amongst all studied compounds, JB-4 showed maximum zone of inhibition against most of the studied bacterial strains while compound JB-2 is least effective. Thus, substitution affects inhibition and methyl salicylate moiety with cinnamaldehyde side chain is most effective. Further, virtual screening of these compounds was done to evaluate molecular properties and bioactive scores of these compounds.

Keywords: azomethines, methyl salicylate, antibacterial activity, agar disc method, DMF, DMSO

Full Text:

PDF (92-98)


Ajabshir, S. Z., Niasari M. S., Hamadanian M., 2015. Praseodymium oxide nanostructures: novel solvent-less preparation, characterization and investigation of their optical and photo catalytic properties. RSC Adv. 5: 33792-33800.

Al-Amiery A. A., Al-Majedy Y. K., Ibrahim H. H., Al-Tamimi-Al-Amiery A. A., 2012. Antioxidant, antimicrobial, and theoretical studies of the thiosemi carbazone derivative Schiff base 2-(2-imino-1-methylimidazolidin-4-ylidene) hydrazine carbothioamide (IMHC). Org. Med. Chem. Lett., 2, 4. doi: 10.1186/2191-2858-2-4.

Álvarez-Fernández E., Cancelo A., Diaz-Vega C., Capita R., Alonso-Calleja C., 2013. Antimicrobial resistance in E. coli isolates from conventionally and organically reared poultry: A comparison of agar disc diffusion and Sensi Test Gram-negative methods. Food Control, 30: 227-234.

Asadi M., Sarvestani A. H., 2001. Synthesis, characterization, and thermodynamics of tertiary phosphine cobalt(III) Schiff-base complexes. Can. J. Chem. 79: 1360 -1365.

Aydogan F., Öcal N., Turgut Z., Yolacan C., 2011. Transformations of aldimines derived from pyrrole-2-carbaldehyde and Synthesis of thiazolidino-fused compounds. Bull Korean Chem. Soc. 22: 476-480

Bardley, M. P., 2002. An overview of the diversity represented in commercially available databases. J. Comp. Aid. Mol. Div., 16: 301-309.

Bekhil A. A., Heshan, Fahwy T.V., Baraka A., 2003. Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d] pyrimidines as anti-inflammatory–anti microbial Agents Eur. J. Med. Chem. 38: 27 -36

Ceglowski M., Schroeder G., 2015. Preparation of porous resin with Schiff base chelating groups for removal of heavy metal ions from aqueous solutions, Chem. Eng. J. 263: 402–411.

Ghose, A. K, Viswanadhan, V. N, Wendoloski, J. J., 1999. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb. Chem. 1: 55–68.

Hashimoto T., Kimura H., Kawamata Y., Maruoka K., 2012., A Catalytic Asymmetric Ugi-type Reaction With Acyclic Azomethine Imines. Ang. Chem. Int. Ed. 51: 7279-7281.

Hesping L., Biswas A., Daniliuc C.G., Lichtenfeld C. M., Studer A., 2015. Stereo selective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides. Chem. Sci. 6: 1252-1257

Hoz A., Diaz-Ortiz A., Moreno A., Sanchez-Migallon A., Prieto P., Carrillo J. R., Vazquez E., Gomez M. V., Herrero, M. A., 2007. Microwave-Assisted Reactions in Heterocyclic Compounds with Applications in Medicinal and Supramolecular Chemistry. Comb. Chem. High Thro. Screen. 10: 877- 902.

Lipinski C. A., 2004. Lead- and drug like compounds: the rule of five revolution. Drug Discovery Today: Techn., 337-341.

Lipinski C. A., Lombardo F., Dominy B. W., Feeney P. J., 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Revs. 23: 3–25.

Oprea, T. I., 2000. Property distribution of drug-related chemical databases. J. Comput. Aid. Mol. Des., 14: 251-264.

Pandey S. N., Sriram D., Nath G., DeClercq E., 1999. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl] thiosemicarbazide. Eur. J. Pharma. Soc. 9: 25-31.

Singh P., Kaur P., Luxami V., Kaur S., Kumar S., 2007. Syntheses and anti-cancer activities of 2-[1-(indol-3-yl-/pyrimidin-5-yl-/pyridine-2-yl-/quinolin-2-yl)-but-3-enyl amino]-2-phenyl ethanols. Bioorg. Med. Chem. 15: 2386-2395.

Sriram D., Yogeeswari P., Kumar, T. G. A., 2005. Microwave assisted synthesis and anti-HIV activity of 2, 3-diaryl-1,3-thiazolidin-4-ones. Ind. J. Pharm. Sci. 67: 96-499.

Sztanke K., Maziarka A., Osinka A., Sztanke M., 2013. An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg. Med. Chem. 21: 3648–3666.

Veber, D. F., Johnson, S. R., Cheng, H. Y., Smith, B. R., Ward, K. W., Kopple, K. D., 2002. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45:2615–2623.

Verma G., Marella A., Mohammad S., Mymoona A., Mohammad R. A., Mohammad M. A., 2014. A review exploring biological activities of hydrazones. J Pharm Bioallied Sci. 6: 69–80.

Yurti A., Bereket G., Kivrak A., Balaban A., Erk B., 2005. Corrosion-Effect of Schiff bases containing pyridyl group as corrosion inhibitors for low carbon steel in 0.1 M HCl. J. Appl. Electrochem., 35: 1025–1032.



  • There are currently no refbacks.


Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Indonesian J Pharm indexed by:

analytics View My Stats