title: Synthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores.
abstract: A variety of 2-(aminomethyl)aziridines was prepared and converted into the corresponding 1,2,3-triaminopropanes through a novel, microwave-assisted and regioselective ring opening by diethylamine in acetonitrile. Antiplasmodial assays revealed antimalarial activity for 2-[(1,2,4-triazol-1-yl)methyl]aziridines and 2-(N,N-diethylaminomethyl)aziridines, as well as for the corresponding 1-(diethylamino)propanes obtained through ring opening, pointing to the relevance of both the 2-(aminomethyl)aziridine and the 1,2,3-triaminopropane unit as novel antimalarial pharmacophores.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Sara
authors.initials: S
authors.lastname: Kenis
authors.forename: Karel
authors.initials: K
authors.lastname: Vervisch
authors.forename: Carmen
authors.initials: C
authors.lastname: Lategan
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Smith
authors.forename: Kelly
authors.initials: K
authors.lastname: Chibale
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*; D011437:Propylamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C558519:1,2,3-triaminopropane; D000962:Antimalarials; D001388:Aziridines; D011437:Propylamines