- -

Isolation Structural Assignment and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline a New Natural Product from Penicillium brevicompactum with in vivo Anti-Juvenile Hormone Activity

RiuNet: Institutional repository of the Polithecnic University of Valencia

Share/Send to

Cited by

Statistics

Isolation Structural Assignment and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline a New Natural Product from Penicillium brevicompactum with in vivo Anti-Juvenile Hormone Activity

Show simple item record

Files in this item

dc.contributor.author Moya, Pilar es_ES
dc.contributor.author Cantin Sanz, Angel es_ES
dc.contributor.author Castillo López, Mª Ángeles es_ES
dc.contributor.author Primo Millo, Jaime es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Primo Yufera, Eduardo es_ES
dc.date.accessioned 2016-11-30T11:50:08Z
dc.date.issued 1998-11-13
dc.identifier.issn 0022-3263
dc.identifier.uri http://hdl.handle.net/10251/74801
dc.description Supporting Information Available: 1H-NMR and 13CNMR spectra of compounds 2-6 (12 pages). es_ES
dc.description.abstract [EN] A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities. es_ES
dc.description.sponsorship The authors acknowledge the financial support of the Institucio´ Valenciana d’Estudis i Investigacio´ (fellowship to A.C.), Comisión Interministerial de Ciencia y Tecnología (CICYT), and Consejeria de Agricultura P. y A. de la C. Valenciana.
dc.language Inglés es_ES
dc.publisher American Chemical Society es_ES
dc.relation.ispartof Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Reverse-turn peptidomimetics es_ES
dc.subject Beta-keto-esters es_ES
dc.subject Electroorganic chemistry es_ES
dc.subject Electrochemical cyclization es_ES
dc.subject Conformational analysis es_ES
dc.subject Organic-synthesis es_ES
dc.subject Biosynthesis es_ES
dc.subject Dipeptides es_ES
dc.subject Discovery es_ES
dc.subject Inhibitor es_ES
dc.subject.classification MICROBIOLOGIA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification BIOQUIMICA Y BIOLOGIA MOLECULAR es_ES
dc.title Isolation Structural Assignment and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline a New Natural Product from Penicillium brevicompactum with in vivo Anti-Juvenile Hormone Activity es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1021/jo972267v
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Industriales - Escola Tècnica Superior d'Enginyers Industrials es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Agrónomos - Escola Tècnica Superior d'Enginyers Agrònoms es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural - Escola Tècnica Superior d'Enginyeria Agronòmica i del Medi Natural es_ES
dc.description.bibliographicCitation Moya, P.; Cantin Sanz, A.; Castillo López, MÁ.; Primo Millo, J.; Miranda Alonso, MÁ.; Primo Yufera, E. (1998). Isolation Structural Assignment and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline a New Natural Product from Penicillium brevicompactum with in vivo Anti-Juvenile Hormone Activity. Journal of Organic Chemistry. 63(23):8530-8535. doi:10.1021/jo972267v es_ES
dc.description.accrualMethod Senia es_ES
dc.relation.publisherversion https://dx.doi.org/10.1021/jo972267v es_ES
dc.description.upvformatpinicio 8530 es_ES
dc.description.upvformatpfin 8535 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 63 es_ES
dc.description.issue 23 es_ES
dc.relation.senia 35066 es_ES


This item appears in the following Collection(s)

Show simple item record