Fluorous synthesis of substituted sclerotigenin library.
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.
Lu
Yimin
Y
Fluorous Technologies, Inc., Pittsburgh, Pennsylvania 15238, USA.
Nagashima
Tadamichi
T
Miriyala
Bruhaspathy
B
Conde
Joanne
J
Zhang
Wei
W
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
D001570:Benzodiazepinones; C539066:sclerotigenin; D005461:Fluorine