Synthesis and Study of Oxazolone Derivatives Showing Biological Activity
Author Affiliations
- 1 Department of Chemistry, Faculty of Science, the Maharaja Sayajirao University of Baroda, Vadodara, INDIA
Res. J. of Pharmaceutical Sci., Volume 1, Issue (3), Pages 1-5, November,30 (2012)
Abstract
Synthesis of the oxazolone ring was performed by the condensation of 4-n –alkoxy benzoyl glycine with appropriate 4-n- alkoxy benzaldehyde in presence of acetic anhydride and anhydrous sodium acetate. Eight compounds were prepared using two different types of 4-n-alkoxy benzaldehyde molecules and compare their percentage yields as well as their activities. Also in both the respective series, the oxazolone rings containing a terminal nitro group were prepared to observe the effect of the electron withdrawing nitro group as compared to that of the electron releasing alkoxy groups. The antibacterial activity was checked against Micrococcus luteus and Escherichia coli for all the compounds. The lower members of each series showed better antibacterial activity than the higher members. Also, the cytotoxicity was checked against dicots (moong seeds; Phaseolus aureus). The presence of alkoxy groups showed no profound effect on the seed germination while the presence of nitro group showed growth inhibitory action. The structures of the synthesized compounds have been characterized by elemental analysis, TLC and spectral data.
References
- Buchardt D., Michael E., Peter N. and Henrik R., U. S. Patent No. 5736336 (1998)
- David C. P., Oxazoles: Synthesis, Reactions and Spectroscopy, Part John Wiley and Sons. London (2004)
- Nicolaou K.C., Claiborner C.F., Nantermet P.G., Liu, J.J., Ueno H., Renaud J. and Guy R.K., Nature, 367 ,630-633 (1994)
- Li Q. and Sham H., Jr . Expert Opinion on Therapeutic Patents,12, 1663-1669 (2002)
- Stork G., La Clair, J.J., Spargo P., Nargund R.P. and Totah N., J. Am. Chem. Soc., 118, 5304-5309 (1996)
- Dave J.S. and Vora R.A., Liquid crystals and ordered fluids, Plenum press, London, 477-480 (1970)
- Vogel’s textbook of Practical Organic Chemistry, fifth edition, Pearson Education Limited, 1073 (2005)
- Mc Donald M.B. and Copeland L.O., Seed Science andTechnology Laboratory Manual, Scientific Publishers, Jodhpur, 232 (1999)
- Nazaritarhan H., Hosseinzadeh A., Alibadi A and Gholamine B., Cytotoxic and apoptogenic properties of 2-phenylthiazole-4-carboxamide derivatives in human carcinoma cell lines, Res. J. Recent Sci. 7(5)(2012)
- Vosooghi M., Rajabalian S., Sorkhi M., Badinloo M., Negahbani A. S., Asadipour A., Mahdavi M., Shafiee A. and Foroumadi A., Synthsis and cytotoxic activity of some 2-amino-4-aryl-3-cyano-7-(dimethylaamino) -4H-chromenes, Res. J. Recent Sci., 9-14 (2010)
- Dalili D., Samadi N. and Sabeti B., The effect of antifungal compounds on cell surface hydrophobicity and adhesion Candida albicans to buccal epithelial cells, Res. J. Recent Sci.,7(5) (2012)