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Molecules ; 23(7)2018 Jun 21.
Artículo en Inglés | MEDLINE | ID: mdl-29933580

RESUMEN

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.


Asunto(s)
Botrytis/efectos de los fármacos , Cinamatos/síntesis química , Fungicidas Industriales/síntesis química , Estirenos/síntesis química , Alquilación , Ascomicetos/efectos de los fármacos , Ascomicetos/crecimiento & desarrollo , Botrytis/crecimiento & desarrollo , Cinamatos/farmacología , Ésteres , Fungicidas Industriales/farmacología , Fusarium/efectos de los fármacos , Fusarium/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Phytophthora/efectos de los fármacos , Phytophthora/crecimiento & desarrollo , Relación Estructura-Actividad , Estirenos/farmacología
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