title: Synthesis and evaluation of phosphoramidate and phosphorothioamidate analogues of amiprophos methyl as potential antimalarial agents.
abstract: A series of phosphoramidate and phosphorothioamidate compounds based on the lead antitubulin herbicidal agents amiprophos methyl (APM) and butamifos were synthesised and evaluated for antimalarial activity. Of these compounds, phosphorothioamidates were more active than their oxo congeners and the nature of both aryl and amido substituents influenced the desired activity. The most active compound was 46, O-ethyl-O-(2-methyl-4-nitrophenyl)-N-cyclopentyl phosphorothioamidate, which was more effective than the lead compound.
authors: Department of Pharmaceutical & Medicinal Chemistry, Royal College of Surgeons in Ireland, Stephens Green, Dublin 2, Ireland.
authors: Christine
authors: C
authors: Mara
authors: Enda
authors: E
authors: Dempsey
authors: Angus
authors: A
authors: Bell
authors: James W
authors: JW
authors: Barlow
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D016778:Malaria, Falciparum / Q000188:drug therapy; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010756:Phosphoric Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects*; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000577:Amides; D000962:Antimalarials; D009578:Nitrobenzenes; D009946:Organothiophosphorus Compounds; D010756:Phosphoric Acids; D050257:Tubulin Modulators; C017823:amiprophos methyl; C011067:phosphoramidic acid