New Biologically Active Compounds from 1,3-Diketones

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New Biologically Active Compounds from 1,3-Diketones

Author Affiliations

¹Department of Chemistry, Gulu University, P.O. Box 166, Gulu, UGANDA
²Department of Chemistry, Makerere University, P.O. Box 7062, Kampala, UGANDA Department of Paediatrics, Faculty of Medicine, Gulu University, P.O. Box 166, Gulu, UGANDA

Res.J.chem.sci., Volume 1, Issue (3), Pages 102-108, June,18 (2011)

Abstract

The ready availability of cyclohexanones and the enhanced reactivity at their -positions render them starting materials of choice in the present study. The synthesis of new compounds of antimicrobial activity was undertaken by the coupling of aromatic amines with 5,5-dimethyl cyclohexan-1,3-dione (dimedone). The products were refluxed with N–benzyl-N-phenylhydrazine in acetic acid. The structures of the products were elucidated using micro- and IR-spectral analyses. They were confirmed using H NMR at 60MHz and TMS as internal standard. The diketone derivatives were tested for their biological activity against gram-positive Cocci and Bacilli, and gram-negative Bacilli. The study showed that the derivatives gave a wide range of activity from inactive to highly active, which proves it to be of fresh pharmaceutical interest.

References

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[ref1] French H.S. and Holden M.E.T., Absorption Spectra of Certain -Unsaturated Ketones, including Benzal Compounds, J. Amer. Chem. Soc., 67, 1239 (1945)

[ref2] Schwarzenbach G. and Wittwer Ch., Über das Keto-Enol-Gleichgewicht bei cyclischen Diketonen, Helv. Chim. Acta 30, 663 (1947)

[ref3] Conroy H., Picrotoxin. II., The Skeleton of Picrotoxinin. The Total Synthesis of dlPicrotoxadiene, J. Amer. Chem. Soc., 74, 3046 1952)

[ref4] Meek E. G., Turnbull J. H. and Wilson W., Alicyclic compounds. Part II. The preparation of cyclohexane-1:3-diones and their enol ethers, J. Chem. Soc. 811 (1953)

[ref5] Shriner R.L. and Todd H.R., 1,3-Cyclohexadione-5,5-dimethyl, Org. Synth., II, 200 (1943)

[ref6] Frank R.L. and Hall H.K., Monocyclic Terpenes from Cyclic 1,3-Diketones, J. Chem. Soc. 72, 1645 (1950)

[ref7] Pal B.C., Dehydration of Phenylethylcyclohexanol-3, J. Amer. Chem. Soc., 11, 3397 (1955)

[ref8] Chitra M., Shyamala D.C.S. and Sukumar E., Antibacterial Activity of Embelin, Filotropia, 74, 401 (2003)

[ref9] Manjudar S.H., Chakra G.S. and Kulkarni K.S., Medicinal Potential of Semecarpus anacardium Nut., J. Herb. Med. Toxicol.,, 9 (2008)

[ref10] Cousinité S., Gressier M., Alphonse P. and Menu M.J., Silica-Based Nanohybrids containing Dipyridine, Urethan, or Urea Derivatives, Chem. Matters, 19, 6492 (2007)

[ref11] Bares J., Richard P., Meunier P., Pirio N., Padelkova Z., Cernoisck Z., Cysarova I. and Ruzicka, A., Reactions of C,N-chelated Tin(II) and Lead(II) Compounds with Zirconocene Dichloride Derivatives, Organometallics, 28, 3105 (2009)