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Syntheses and antimicrobial activities of amide derivatives of 4-[(2-isopropyl-5-methylcyclohexyl)oxo]-4-oxobutanoic acid
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Abstract
Chiral 4-[(2-isopropyl-5-methylcyclohexyl)oxo]-4-oxobutanoic acid reacts with substituted anilines to produce amides 1-6 in high yields. Resulted amides 1-6 were investigated for their antifungal and antibacterial activities. Compounds 2 (96.5%) against Aspergillus fumigatus and 6 (93.7%) against Helminthosporium sativum demonstrated excellent activities. However, compounds 3 (37.6%) against Bacillus subtilis , 4 (33.2%) against Pseudomonas aurignosa , 5 against Klebsiella pneumonia demonstrated excellent growth inhibition potential.
KeywordsChiral 4-[(2-isopropyl-5-methylcyclohexyl)- oxo]-4-oxobutanoic AcidSubstituted AnilinesAmidesAntimicrobial Activity
- James, J.K., Foster, J.R., Lentino, R.S., Cathy D. (1986) Comparison of in vitro activity of quinolone antibiotics and vancomycin against gentamicin—And methicillin— Resistant Staphylococcus aureus by time—Kill kinetic studies. Antimicrobial Agents and Chemotherapy, 30, 823-827.
- Nwakaso, N., Umejiego, D., Gollapalli, L., Shaeling, A.J. and Lu, L.H. (2008) Targeting a prokaryotic protein in a eukaryotic pathogen: Identification of lead compounds against cryptosporidiosis. Chemistry & Biology, 15, 70- 77. doi:10.1016/j.chembiol.2007.12.010
- Allemandi, D.A., Alovero, F.L. and Manzo, R.H. (1994) In vitro activity of new sulphanilyl fluoroquinolones against Staphylococcus aureus. Journal Antimicrobial Chemotherapy, 34, 261-264. doi:10.1093/jac/34.2.261
- Cupido, T., Tulla-Puche, J., Spengler, J. and Albericio, F. (2007) The synthesis of naturally occuring peptides and their analogs. Current Opinion in Drug Discovery and Development, 10, 768-783.
- Bode, J.W. (2006) Emerging methods in amide- and peptide-bond formation. Current Opinion in Drug Discovery and Development, 9, 765-775.
- Han, S.-Y. and Kim, Y.-A. (2004) Recent development of peptide coupling reagents in organic synthesis. Tetrahe- dron, 60, 2447-2467. doi:10.1016/j.tet.2004.01.020
- Montalbetti, C.A.G.N. and Falque, V. (2005) Amide bond formation and peptide coupling. Tetrahedron, 61, 10827- 10852. doi:10.1016/j.tet.2005.08.031
- K?hn, M. and Breinbauer, R. (2004) The staudinger ligation-A gift to chemical biology. Angewandte Chemie International Edition, 43, 3106-3116. doi:10.1002/anie.200401744
- Martinelli, J.R., Clark, T.P., Watson, D.A., Munday, R.H., Buchwald, S.L. (2007) Palladium-catalyzed aminocar- bonylation of aryl chlorides at atmospheric pressure: The dual role of sodium phenoxide. Angewandte Chemie International Edition, 46, 8460-8463. doi:10.1002/anie.200702943
- Chang, J.W.W. and Chan, P.W.H. (2008) Highly efficient ruthenium (II) porphyrin catalyzed amidation of alde- hydes. Angewandte Chemie International Edition, 47, 1138-1140. doi:10.1002/anie.200704695
- Bose, A.K., Manhas, M.S., Banik, B.K. and Srirajan, V. (2000) The amide linkage: Selected. Structural aspects in chemistry, biochemistry, and material science. In: Green- berg, A., Breneman; C.M., Liebman J.F., Eds., Wiley- Interscience, New York, 157.
- Zabicky, J. (1970) The chemistry of amides interscience. London.