5831-75-4Relevant academic research and scientific papers
Acyl-CoA::cholesterol O-Acyl Transferase (ACAT) Inhibitors. 1. 2-(Alkylthio)-4,5-diphenyl-1H-imidazoles as Potent Inhibitors of ACAT
Harris, Neil V.,Smith, Christopher,Asthon, Michael J.,Bridge, Andrew W.,Bush, Raymond C.,et al.
, p. 4384 - 4392 (2007/10/02)
A potent, bioavailable ACAT inhibitor may have beneficial effects in the treatment of atherosclerosis by (i) reducing the absorption of dietary cholesterol, (ii) reducing the secretion of very low density lipoproteins into plasma from the liver, and (iii) preventing the transformation of arterial macrophages into foam cells.We have found that a mevalonate derivative 2, which contains a 4,5-diphenyl-1H-imidazol-2-yl moiety, inhibits rat hepatic microsomal ACAT in vitro and produces a significant hypocholesterolemic effect in the cholesterol-fed rat.Structure-activity relationships for analogues of 2 demonstrate that the 4,5-diphenyl-1H-imidazole moiety is a pharmacophore for inhibition of rat microsomal ACAT.
Synthesis and Reactions of Iodo Lactams
Knapp, Spencer,Levorse, Anthony T.
, p. 4006 - 4014 (2007/10/02)
The synthesis of a series of iodo lactams has been achieved by a new cyclization method that depends on generating N,O-bis(trimethylsilyl)imidate derivatives as intermediates.Treatment of an unsaturated amide with trimethylsilyl triflate in pentane and then iodine in tetrahydrofuran gives the iodo lactam.Some reactions of this new difunctional group with bases, nucleophiles, and Michael acceptors leading to functionalized or elaborated lactams are presented.In general, iodo lactams undergo direct SN2 reactions with reactive (but weakly basic) nucleophiles like azide and triphenylphosphine and elimination or decomposition in the presence of bases or basic nucleophiles.Sodium hydride may be used to generate an N-acylaziridine intermediate, which can be opened with azide to deliver an azido lactam with overall retention of stereochemistry.Silver-assisted solvolysis of iodo lactams gives the hydroxy lactams with retention of configuration, probably also because of participation by the lactam nitrogen.The sodium salt of 5-(iodomethyl)-2-pyrrolidinone (3), generated at -20 deg C, undergoes an annulation reaction with unsaturated esters (but not sulfones), leading to pyrrolizidine derivatives.
A PROCEDURE FOR "IODOLACTAMIZATION"
Knapp, Spencer,Rodriques, Karen E.,Levorse, Anthony T.,Ornaf, Raphael M.
, p. 1803 - 1806 (2007/10/02)
Treatment of an unsaturated amide with TMS-OTf, then iodine in THF gives the iodolactam.
