Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Heterocyclic Chalcone Derivatives and Their Radical Scavenging Ability Toward 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) Free Radicals

  • Hwang, Ki-Jun (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University) ;
  • Kim, Ho-Seok (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University) ;
  • Han, In-Cheol (Department of Bioactive Material Sciences, College of Natural Science, Chonbuk National University) ;
  • Kim, Beom-Tae (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University)
  • Received : 2012.04.24
  • Accepted : 2012.05.07
  • Published : 2012.08.20
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Abstract

A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring-containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalones was distinctly demonstrated in our work.

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