Semisynthesis of new tetrahydrofuranic alkyl ester and furano-pyrone derivatives as inhibitors of the mitochondrial complex I

Autor:	Almudena Bermejo, M. Carmen Zafra-Polo, Adrien Cavé, Eva Peris, Diego Cortes, Ernesto Estornell, Bruno Figadère
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Altholactone Stereochemistry Organic Chemistry Biochemistry Semisynthesis Chemical correlation Pyrone Goniofupyrone chemistry.chemical_compound chemistry Drug Discovery Spectral data Alkyl Mitochondrial Complex I
Zdroj:	Tetrahedron. 58:1335-1342
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)01234-0
Popis:	Methoxymethylation of altholactone ( 1 ) led to the corresponding O -methoxymethyl derivative ( 3 ) in addition to the unexpected 6,7-dihydro-7-methoxy analogue ( 4 ), and two original tetrahydrofuranic (THF) alkyl esters ( 5 , 6 ). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone ( 7 ) through 7-hydroxylation of 1 in acid medium, a minor compound ( 8 ) with an identical skeleton to that of compounds 5 and 6 was identified. Careful examination of the published spectral data of the reported styryl-lactones with an heptolide skeleton reveals that those structures possess also a THF alkyl ester skeleton. The revision of those structures was confirmed by chemical correlation. All altholactone derivatives assayed proved to be specific inhibitors of the mitochondrial complex I.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e190ee5bd2d71c97a602e019b15e56da https://doi.org/10.1016/s0040-4020(01)01234-0 Zobrazit plný text záznamu Full Text from ScienceDirect