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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 12: 3197 - 3203

DOI: https://doi.org/10.6023/cjoc201807004

Articles

Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety

  • Zhang Xiaoming ,
  • Lei Peng ,
  • Li Xinlu ,
  • Yang Xinling ,
  • Zhang Xuebo ,
  • Sun Tengda ,
  • Ling Yun
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  • Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193

Received date: 2018-07-02

  Revised date: 2018-07-24

  Online published: 2018-09-05

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472236).

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Abstract

Based on the structure of natural product aspernigerin, a series of novel tetrahydroquinoline compounds containing thiocarbonyl moiety were designed and synthesized. The structures of the title compounds were confirmed by 1H NMR, 13C NMR and HRMS, and the crystal structure of (E)-3-(4-fluorophenyl)-1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl) piperazin-1-yl)prop-2-en-1-one (5J) was determined by X-ray single crystal diffraction. The bioassay results indicated that (E)-1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl)piperazin-1-yl)-3-(o-tolyl)prop-2-en-1-one (5b) exhibited good anti-fungual activity against Valsa mali (EC50=3.04 μg/mL), which was better than the commercial fungicide fluoramide (EC50=9.16 μg/mL).

Key words： natural product; aspernigerin; tetrahydroquinoline; synthesis; anti-fungal activity

Cite this article

Zhang Xiaoming , Lei Peng , Li Xinlu , Yang Xinling , Zhang Xuebo , Sun Tengda , Ling Yun . Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety[J]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3197 -3203 . DOI: 10.6023/cjoc201807004

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