Jozipeltine A, a Novel, Unnatural Dimer of the Highly Hydroxylated Naphthylisoquinoline Alkaloid Dioncopeltine A

Autor:	Kim Messer, Gerhard Bringmann, Wael Saeb, Reto Brun, Michael Wohlfarth
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Chemistry Stereochemistry Alkaloid Reagent Dimer Organic Chemistry Drug Discovery Side chain Molecule Biochemistry
Zdroj:	Tetrahedron. 56:5871-5875
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(00)00538-x
Popis:	The synthesis of jozipeltine A (5), the 6′-coupled constitutionally symmetric dimer of the highly antimalarial naphthylisoquinoline alkaloid dioncopeltine A (4), is described. After selective protection of two of the four OH- and NH-functionalities of 4, the coupling succeeds oxidatively, with Ag2O as the reagent. Deprotection gives the target molecule 5, in only three steps from 4. Jozipeltine A is the first naphthylisoquinoline dimer with oxygen functions in the side chain of the naphthalene part. Investigations on its antiplasmodial and antiviral activities provide valuable insight into structure–activity relationships within this promising class of bioactive quateraryls.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::490d278ec179b626947c90ebe2dce7a9 https://doi.org/10.1016/s0040-4020(00)00538-x Zobrazit plný text záznamu Full Text from ScienceDirect