1402041-08-0Relevant articles and documents
A Platform of Regioselective Methodologies to Access Polysubstituted 2-Methyl-1,4-naphthoquinone Derivatives: Scope and Limitations
Rodo, Elena Cesar,Feng, Liwen,Jida, Mouhamad,Ehrhardt, Katharina,Bielitza, Max,Boilevin, Jérémy,Lanzer, Michael,Williams, David Lee,Lanfranchi, Don Antoine,Davioud-Charvet, Elisabeth
, p. 1982 - 1993 (2016/04/26)
A platform of synthetic methodologies has been established to access a focused library of polysubstituted 3-benzylmenadione derivatives functionalized on the aromatic ring of the naphthoquinone core. Two main routes were explored: 1) The naphthol route, starting from either an α-tetralone or a propiophenone, and 2) the regioselective Diels-Alder reaction, starting from various dienes and two 2-bromo-5(or 6)-methyl-1,4-benzoquinones. 6-Substituted 2-methylnaphthols were synthesized by using a xanthate-mediated free-radical addition/cyclization sequence for the construction of the 6-substituted menadione subunit. Furthermore, an efficient and simple new pathway that allows the formation of 6- or 7-substituted 3-(substituted-benzyl)menadione regioisomers from a common commercial scaffold has also been developed by the naphthol route, advantageous with regard to step economy. Our synthetic methodologies exemplified by 34 compounds have allowed structure-activity relationships to be deduced for use as the basis for the development of new antimalarial redox-active polysubstituted benzylmenadione derivatives.
Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents
-
Paragraph 0165-0170, (2013/03/26)
Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.
