title: Biomimetic synthesis and biological evaluation of Aplidiopsamine A.
abstract: The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.
authors.forename: Joseph D
authors.initials: JD
authors.lastname: Panarese
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001315:Australia; D001927:Brain Diseases / Q000188:drug therapy; D015394:Molecular Structure; D058988:Phosphodiesterase 4 Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011758:Pyrroles; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014561:Urochordata / Q000737:chemistry
chemical_list: D000470:Alkaloids; D058988:Phosphodiesterase 4 Inhibitors; D011758:Pyrroles; D011804:Quinolines; C555847:aplidiopsamine A