title: Synthesis of a library of "lead-like" γ-lactams by a one pot, four-component reaction.
abstract: The synthesis of a pilot scale library of 116 structurally diverse γ-lactams is reported. The library core structure emanates from a γ-lactam forming one-pot, four-component reaction of ammonium acetate, p-methoxythiophenol, p-methoxybenzaldehyde, and maleic anhydride. Structural diversity then arises from amide coupling, thioaryl cleavage, N-functionalization, and heterocycle forming reactions on this core structure. Computational analysis reveals that the library contains molecular properties and shape diversity suitable for drug lead and biological probe discovery.
authors.affiliation: Department of Chemistry, One Shields Ave, University of California , Davis, California 95616, United States.
authors.forename: Kevin S
authors.initials: KS
authors.lastname: Martin
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Di Maso
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
mesh_terms: D000085:Acetates / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008299:Maleic Anhydrides / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000085:Acetates; D000577:Amides; D001547:Benzaldehydes; D007769:Lactams; D008299:Maleic Anhydrides; D010636:Phenols; D054852:Small Molecule Libraries; D013438:Sulfhydryl Compounds; C042983:thiophenol; C024896:4-anisaldehyde