title: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 8. Side chain ether analogues of lovastatin.
abstract: A general route for preparing side chain ether analogues of lovastatin is presented. These analogues proved to be weaker inhibitors of HMG-CoA reductase than the corresponding side chain ester analogues. Interestingly, inhibitory potency was enhanced markedly when the 4-fluoro group was incorporated in the aromatic moiety of the side chain benzyl group of 2d.
authors.affiliation: Merck Sharp & Dohme Research Laboratories, West Point, Pennsylvania 19486.
authors.forename: T J
authors.initials: TJ
authors.lastname: Lee
authors.forename: W J
authors.initials: WJ
authors.lastname: Holtz
authors.forename: R L
authors.initials: RL
authors.lastname: Smith
authors.forename: A W
authors.initials: AW
authors.lastname: Alberts
authors.forename: J L
authors.initials: JL
authors.lastname: Gilfillan
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D004952:Esters; D004987:Ethers; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D008148:Lovastatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D004987:Ethers; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; C070474:6-(2-(8-((4-fluorobenzyl)oxy)-1,2,6,7,8,8a-hexahydro-2,6-dimethyl-1-naphthyl)ethyl)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one; D008148:Lovastatin