Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives
| Autor: | Luanbin Huang, Ming-An Ouyang, Zengwei Lian, Huiyou Xu, Qiuju Shen, Ting Chen, Yan Shi, Liyan Song |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Phytophthora
Alkylation Stereochemistry Substituent Pharmaceutical Science Microbial Sensitivity Tests 010402 general chemistry 01 natural sciences Chemical synthesis Article Analytical Chemistry Styrenes lcsh:QD241-441 chemistry.chemical_compound Structure-Activity Relationship Ascomycota Fusarium lcsh:Organic chemistry Amide Drug Discovery Structure–activity relationship Physical and Theoretical Chemistry Alkyl chemistry.chemical_classification 010405 organic chemistry Chemistry Organic Chemistry antifungal activity Esters Carbon-13 NMR 0104 chemical sciences Fungicides Industrial Chemistry (miscellaneous) Cinnamates Propargyl derivatives Molecular Medicine Lansiumamide B Botrytis chemical synthesis SAR |
| Zdroj: | Molecules Volume 23 Issue 7 Molecules, Vol 23, Iss 7, p 1499 (2018) Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules23071499 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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