title: Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines.
abstract: A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC(50)-values ranging between 150 and 680 nM.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Vandekerckhove
authors.forename: Christian
authors.initials: C
authors.lastname: Müller
authors.forename: Dieter
authors.initials: D
authors.lastname: Vogt
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
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D016466:CHO Cells; D002384:Catalysis; D002470:Cell Survival / Q000187:drug effects; D002738:Chloroquine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000633:toxicity; D006224:Cricetinae; D003412:Cricetulus; D004353:Drug Evaluation, Preclinical; D010963:Plasmodium falciparum / Q000187:drug effects; D012238:Rhodium / Q000737:chemistry
chemical_list: D000962:Antimalarials; D002738:Chloroquine; D012238:Rhodium