title: Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides.
abstract: The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide derivatives have been assayed against several enzymes that hold potential for the development of new drugs to battle bacterial infections and Alzheimer's disease. Compounds 20c and 20e showed promising selective sub-micromolar inhibition of human butyrylcholinesterase [Formula: see text] ([Formula: see text] values [Formula: see text] and [Formula: see text], respectively).
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000, Ljubljana, Slovenia. uros.groselj@fkkt.uni-lj.si.
authors.forename: Uroš
authors.initials: U
authors.lastname: Grošelj
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000, Ljubljana, Slovenia.
authors.forename: Amalija
authors.initials: A
authors.lastname: Golobič
authors.affiliation: Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia.
authors.forename: Damijan
authors.initials: D
authors.lastname: Knez
authors.affiliation: Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia.
authors.forename: Martina
authors.initials: M
authors.lastname: Hrast
authors.affiliation: Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia.
authors.forename: Stanislav
authors.initials: S
authors.lastname: Gobec
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000, Ljubljana, Slovenia.
authors.forename: Sebastijan
authors.initials: S
authors.lastname: Ričko
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000, Ljubljana, Slovenia.
authors.forename: Jurij
authors.initials: J
authors.lastname: Svete
mesh_terms: D000544:Alzheimer Disease / Q000188:drug therapy; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001424:Bacterial Infections / Q000188:drug therapy; D002091:Butyrylcholinesterase / Q000378:metabolism; D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure
chemical_list: D000577:Amides; D002800:Cholinesterase Inhibitors; D002164:Camphor; C006881:10-camphorsulfonic acid; D002091:Butyrylcholinesterase
keywords: 10-Iodocamphor; Biological evaluation; Butyrylcholinesterase inhibitor; Camphor-derived amines; Curtius rearrangement; Grob fragmentation