title: γ-Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones Synthesized from a Common Amino Ketone Intermediate.
abstract: To investigate diazepinone analogues as γ-turn mimics, seven 1,4-benzodiazepin-2-ones 6 and fourteen pyrrolo[1,2-d][1,4]benzodiazepin-6-ones 4 and 5 were synthesized from 1-(2-aminophenyl)pent-4-en-1-one (7). Acylation of aniline 7 with N-Boc-amino acids, olefin oxidation, Boc removal, and intramolecular Paal-Knorr condensation gave 4 and 5. Alternatively, Boc removal prior to oxidation gave benzodiazepinones 6, which were converted to 4 by ozonolysis and cyclization. Comparison of dihedral angle values for the amino acid component from X-ray analyses of 4g, 5f, and 6f and related diazepinones has catalogued the manner by which ring substituents affect the component's ability to mimic the central residues of γ-turns.
authors.affiliation: Département de Chimie, Université de Montréal, C.P.6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
authors.forename: Aurélie A
authors.initials: AA
authors.lastname: Dörr
authors.affiliation: Département de Chimie, Université de Montréal, C.P.6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
authors.forename: William D
authors.initials: WD
authors.lastname: Lubell
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010422:Pentanones / Q000737:chemistry*
chemical_list: C000602346:1-(2-aminophenyl)pent-4-en-1-one; D000596:Amino Acids; D000814:Aniline Compounds; D001570:Benzodiazepinones; D007659:Ketones; D010422:Pentanones; D001569:Benzodiazepines