title: Addition of thiols to o-quinone methide: new 2-hydroxy-3-phenylsulfanylmethyl[1,4]naphthoquinones and their activity against the human malaria parasite Plasmodium falciparum (3D7).
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).
authors.affiliation: Universidade de São Paulo, Instituto de Biociências, Departamento de Fisiologia, 05508-900 São Paulo, Brazil.
authors.forename: Abhinay
authors.initials: A
authors.lastname: Sharma
authors.forename: Isabela O
authors.initials: IO
authors.lastname: Santos
authors.forename: Pratibha
authors.initials: P
authors.lastname: Gaur
authors.forename: Vitor F
authors.initials: VF
authors.lastname: Ferreira
authors.forename: Celia R S
authors.initials: CR
authors.lastname: Garcia
authors.forename: David R
authors.initials: DR
authors.lastname: da Rocha
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology*; D002478:Cells, Cultured; D005434:Flow Cytometry; D006801:Humans; D045563:Indolequinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016778:Malaria, Falciparum; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000962:Antimalarials; D045563:Indolequinones; D009285:Naphthoquinones; D013438:Sulfhydryl Compounds; C068040:quinone methide; C008252:lapachol; C005090:lawsone