Portal de Periódicos da CAPES

Isolation of N -(2-Methyl-3-oxodecanoyl)pyrrole and N -(2-Methyl-3-oxodec-8-enoyl)pyrrole, Two New Natural Products from Penicillium brevicompactum , and Synthesis of Analogues with Insecticidal and Fungicidal Activity

1998; American Chemical Society; Volume: 46; Issue: 11 Linguagem: Inglês

10.1021/jf9800763

1520-5118

Ángel Cantı́n, Pilar Moya, Miguel A. Miranda, Jaime Primo, Eduardo Primo‐Yúfera,

Microbial Natural Products and Biosynthesis

Two new natural products have been isolated from culture broth of Penicillium brevicompactum Dierckx. The structures have been assigned as N-(2-methyl-3-oxodecanoyl)pyrrole and N-(2-methyl-3-oxodec-8-enoyl)pyrrole on the basis of spectral data. Synthesis of analogues has been carried out by acylation of the pyrrole ring at C2 with different acylated Meldrum's acids. Two analogues (6b and 7b) have shown interesting insecticidal activities, and three other ones (6a, 6c, and 7a) have exhibited significant broad-spectrum fungicidal activities. These synthetic products might be considered as a starting point in the search for new pesticides. Keywords: Penicillium brevicompactum; fungal metabolites; Meldrum's acid; 2-(3-oxoacyl)pyrrole; insecticide; fungicide