Cholesterol surrogates incorporating a benzophenone as part of the sterol tetracycle.
Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.
Gan
Yonghong
Y
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Spencer
Thomas A
TA
D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D003500:Cyclization; D005347:Fibroblasts; D008958:Models, Molecular; D015394:Molecular Structure
D001577:Benzophenones; C047723:benzophenone; D002784:Cholesterol