Abstract
A series of 36 new phenylsulfanylmethyl[1,4]naphthoquinones (7-42) were synthesized by a three-component reaction that involves lawsone, the appropriate aldehyde and thiols with variable substitution patterns. These reactions involve the in situ generation of o-quinone methides (o-QM) via Knoevenagel condensation and 1,4-nucleophilic addition under conventional heating or microwave irradiation. The new naphthoquinones obtained by this methodology were shown to have moderate to good in vitro antimalarial activity against Plasmodium falciparum (3D7).
Copyright © 2012 Elsevier Masson SAS. All rights reserved.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Antimalarials / chemical synthesis*
-
Antimalarials / pharmacology*
-
Cells, Cultured
-
Flow Cytometry
-
Humans
-
Indolequinones / chemical synthesis
-
Indolequinones / chemistry
-
Indolequinones / pharmacology
-
Malaria, Falciparum
-
Molecular Structure
-
Naphthoquinones / chemical synthesis*
-
Naphthoquinones / chemistry
-
Naphthoquinones / pharmacology*
-
Plasmodium falciparum / drug effects*
-
Sulfhydryl Compounds / chemical synthesis*
-
Sulfhydryl Compounds / chemistry
-
Sulfhydryl Compounds / pharmacology
Substances
-
Antimalarials
-
Indolequinones
-
Naphthoquinones
-
Sulfhydryl Compounds
-
quinone methide
-
lapachol
-
lawsone