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Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2018 Jun 21; Vol. 23 (7). Date of Electronic Publication: 2018 Jun 21. - Publication Year :
- 2018
-
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 <superscript>13</superscript> C 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.
- Subjects :
- Alkylation
Ascomycota drug effects
Ascomycota growth & development
Botrytis growth & development
Cinnamates pharmacology
Esters
Fungicides, Industrial pharmacology
Fusarium drug effects
Fusarium growth & development
Microbial Sensitivity Tests
Phytophthora drug effects
Phytophthora growth & development
Structure-Activity Relationship
Styrenes pharmacology
Botrytis drug effects
Cinnamates chemical synthesis
Fungicides, Industrial chemical synthesis
Styrenes chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 23
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 29933580
- Full Text :
- https://doi.org/10.3390/molecules23071499