title: Fluorous synthesis of substituted sclerotigenin library.
abstract: A fluorous linker-assisted synthetic protocol has been developed for preparation of sclerotigenin-type benzodiazepine-quinazolinone library containing 144 analogues. Amide coupling of fluorous trimethoxybenzyl (TMB)-protected amino esters with anthranilic acids followed by base-promoted cyclizations afforded 4-benzodiazepine-2,5-diones. Further derivatization of benzodiazepinediones by reacting with azidobenzoyl chlorides, cyclization, and fluorous linker cleavage afforded the desired compound library. The reaction intermediates were purified by fluorous solid-phase extraction (F-SPE) and final products were further purified by prep-HPLC.
authors.affiliation: Fluorous Technologies, Inc., Pittsburgh, Pennsylvania 15238, USA.
authors.forename: Yimin
authors.initials: Y
authors.lastname: Lu
authors.forename: Tadamichi
authors.initials: T
authors.lastname: Nagashima
authors.forename: Bruhaspathy
authors.initials: B
authors.lastname: Miriyala
authors.forename: Joanne
authors.initials: J
authors.lastname: Conde
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
mesh_terms: D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001570:Benzodiazepinones; C539066:sclerotigenin; D005461:Fluorine