Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives

  • Molecules. 2018 Jun 21;23(7):1499. doi: 10.3390/molecules23071499.
Huiyou Xu  1 ,  Ting Chen  2 ,  Luanbin Huang  3 ,  Qiuju Shen  4 ,  Zengwei Lian  5 ,  Yan Shi  6 ,  Ming-An Ouyang  7 ,  Liyan Song  8
Affiliations
  • 1. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 2. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 3. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 4. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 5. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 6. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 7. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
  • 8. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. [email protected].
PMID: 29933580 DOI: 10.3390/molecules23071499
Abstract

A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (N-methyl-N-cis-styryl-cinnamamide, 2) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, ¹H NMR, and 13C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide Antifungal spectrum. The relationship between different substituents on the amide nitrogen and Antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of N-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the Antifungal activities.

Keywords
Lansiumamide B; SAR; antifungal activity; chemical synthesis; derivatives.
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