Synthesis, Characterization and in vitro Antioxidant Activity of New Chiral N-boc Organotellurium Compounds, (CH3)3OC(O)NHCH(R)C(O)NHCH2-CH2Te-C6H4-4-OCH3, Containing Carbamate and Peptide Groups

• Published in: Journal of the Brazilian Chemical Society 2016-06, Vol.27 (7), p.1157-1164
• Main Authors: Revanna, Rajegowda H., Panchangam, Raghavendra K., Bhanu, Udaya, Doddavenkatanna, Suresh
• Format: Article
• Language: Portuguese
• Subjects: CHEMISTRY, MULTIDISCIPLINARY
• ISSN: 1678-4790
• DOI: 10.5935/0103-5053.20160011

Synthesis, characterization and antioxidant activity of a new series of chiral N-boc oraganotellurium compounds, (CH3)3OC(O)NHCH(R)C(O)NHCH2CH2Te-C6H4-4-OCH3, containing carbamate and peptide groups have been reported in this paper. These chiral peptides were synthesized in good to excellent yields, via acid-amine coupling reaction of N-boc L-amino acids with 2-(4-methoxyphenyltelluro) ethylamine in presence of dicyclohexyl carbodimide (DCC) at room temperature. The elemental analyses, Fourier transform infrared (FTIR), 1H and 13C {1H} nuclear magnetic resonance (NMR) spectra and mass spectra were characteristic. Specific optical rotation (SOR) was also determined. In vitro antioxidant activity of these multi-functional compounds in methanol has been evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with 2,6-di-tert-butyl-4-methylphenol (BHT) as a standard reference compound. The IC50 (inhibitory concentration 50) values of these chiral peptides revealed significant inhibition against DPPH radicals and found to be effective antioxidants.