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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2141 - 2147

DOI: https://doi.org/10.6023/cjoc201204001

Articles

Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

  • Wu Jianzhang ,
  • Li Wulan ,
  • Chen Lingzi ,
  • Chu Shenghui ,
  • Zhao Chenguang ,
  • Wei Tao ,
  • Yang Shulin ,
  • Li Xiaokun
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  • a Institute of Biotechnology, Nanjing University of Science and Technology, Nanjing 210094;
    b School of Pharmacy, Wenzhou Medical College, Wenzhou 325035;
    c College of Information Science and Computer Engineering, Wenzhou Medical College, Wenzhou 325035

Received date: 2012-04-01

  Revised date: 2012-06-18

  Online published: 2012-07-02

Supported by

Project supported by the Technology Foundation for Medical Science of Zhejiang Province (No. 2012KYA129), the Project of Wenzhou Sci & Tech Bureau (No. 20090101), and the Technology Foundation for Chinese Medicine of Zhejiang Province (No. 2012ZB102).

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Abstract

To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by 1H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of B1 was monoclinic system, space group C2/c, with cell dimensions of a＝21.350(3) Å, b＝8.6256(10) Å, c＝26.161(3) Å. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types of chalcones analogs, the compounds with 3,4-(OH)2 in “a” ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.

Key words： chalcones; spiro-heterocyclic; synthesis; DPPH; antioxidant activities; crystal structure

Cite this article

Wu Jianzhang , Li Wulan , Chen Lingzi , Chu Shenghui , Zhao Chenguang , Wei Tao , Yang Shulin , Li Xiaokun . Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2141 -2147 . DOI: 10.6023/cjoc201204001

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