Synthesis and biological evaluation of new analogues of the active fungal metabolites N-(2-methyl-3-oxodecanoyl)-2-pyrroline and N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (II).
New analogues of the bioactive enamides isolated from P. brevicompactum (2 and 3) have been synthesized to improve the biological activities. Two different structural modifications have been introduced: substitution of the aliphatic side chain present in the natural products (1-4) by other groups frequently found in other active compounds and use of other nitrogen-containing five-membered rings with different degrees of oxidation. In this way, the insecticidal and fungicidal activities have been improved. Thus, compound 9, which possess a 3-pyrroline ring, exhibited important insecticidal activity against third-instar nymphs of Oncopeltus fasciatus Dallas (100% mortality at 7.5 microg/cm(2)). Remarkable fungicidal activity was also found, and preliminary structure-activity relationships could be established.
Cantín
A
A
Instituto de Tecnología Química UPV-CSIC and Departamento de Química, Universidad Politécnica de Valencia, Spain.
Moya
P
P
Miranda
M A
MA
Primo
J
J
Primo-Yúfera
E
E
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D007313:Insecta / Q000382:microbiology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry* / Q000502:physiology; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology*; D013057:Spectrum Analysis
D000935:Antifungal Agents; C412904:N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline; C412903:N-(2-methyl-3-oxodecanoyl)-2-pyrroline; D011758:Pyrroles