title: Synthesis and comparison of the biological activity of monocyclic phosphonate, difluorophosphonate and phosphate analogs of the natural AChE inhibitor cyclophostin.
abstract: New monocyclic phosphate, phosphonate and difluorophosphonate analogs of the natural AChE inhibitor cyclophostin were synthesized and their activity toward human AChE examined. Surprisingly, the phosphate, phosphonate, and difluorophosphonate analogs all showed diminished activity when compared with the natural product.
authors.affiliation: Department of Chemistry and Biochemistry and the Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
authors.forename: Benjamin P
authors.initials: BP
authors.lastname: Martin
authors.affiliation: Department of Chemistry and Biochemistry and the Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
authors.forename: Elena
authors.initials: E
authors.lastname: Vasilieva
authors.affiliation: Department of Chemistry and Biochemistry and the Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
authors.forename: Cynthia M
authors.initials: CM
authors.lastname: Dupureur
authors.affiliation: Department of Chemistry and Biochemistry and the Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA. Electronic address: cspill@umsl.edu.
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Spilling
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D054879:Halogenation; D006801:Humans; D010755:Organophosphates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D002800:Cholinesterase Inhibitors; D010755:Organophosphates; D063065:Organophosphonates; D009943:Organophosphorus Compounds; C083659:cyclophostin; D000110:Acetylcholinesterase
keywords: Acetyl cholinesterase; Cyclic phosphate; Cyclic phosphonate; Difluorophosphonate; Inhibition