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Authors
Affiliations
1 Department of Chemistry, Siddaganga Institute of Technology, Tumakuru, Karnataka, IN
Source
International Journal of Innovative Research and Development, Vol 5, No 11Sp (2016), Pagination: 129-135
Abstract
An efficient protocol for the synthesis of N-protected diazomethylketone was developed using (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylamino-morpholinomethylene) methanaminium hexa-fluorophosphate (COMU) and N-nitrosourea (NNU) is developed. Conversion of carboxylic acids to diazomethylketones in an excellent yield was obtained under milder reaction conditions, through a simple workup. Further, the synthesized compounds were used for the preparation of bromomethylketones using 45% aqueous HBr and selenazoles. Prepared bromomethylketones were subjected for their antibacterial activity against Escherichia coli and Staphylococcus aureus strains and antioxidant studies. Antibacterial activity reveals that the compound Fmoc-Phe-CO-CH2-Br exhibited the zone of inhibition with respect to Streptomycin sulphate standard. For antioxidant assay, % RSC of Fmoc-Ala-CO-CH-N2, Fmoc-Phe-CO-CH2-Br and Fmoc-Phe-CO-CH-N2 exhibited free radical inhibition or scavenger activity with 2, 2-diphenyl-1-picrylhydrazyl (DPPH). The synthesized compounds were characterized by HRMS, 1H NMR, and 13C NMR studies.
Keywords
N-Protected Diazomethyl Ketone, Bromomethyl Ketone, Selenazole, COMU, NNU, Antibacterial and Antioxidant Studies.
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