91-03-2Relevant articles and documents
Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives
Nicolle, Simon M.,Lewis, William,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 3749 - 3753 (2016/04/05)
A highly stereoselective route to functionalized pyrrolidines by the metal-catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction. The metal-catalyzed reaction of diazocarbonyl compounds with β-aminoketone derivatives leads to highly substituted pyrrolidines with excellent diastereoselectivity under mild reaction conditions. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction.
Synthesis and pharmacological studies of 3-amino-2-methyl-1-phenylpropanones as hypolipidemic agents in rodents
Huang, Yunsheng,Hall, Iris H.
, p. 329 - 338 (2007/10/03)
A series of 3-amino-2-methyl-1-phenylpropanones were synthesized and proven to have potent hypolipidemic activity in rodents by lowering both serum cholesterol and triglyceride levels at 8 mg/kg/day, i.p. and orally. Many of these analogs showed significantly higher activity than standard drugs, lovastatin and clofibrate at their therapeutic doses. 2-Methyl-3-(perhydroazepin-1-yl)-1-phenylpropanone (4), 3-(4-methylpiperazin-1-yl)-1-phenylpropanone (5), and 2-methyl-3-(4-pyrrolidinocarbonylmethylpiperazin-1-yl)-1-(4-fluorophen yl)propanone (17) showed the best overall activities in lowering both serum cholesterol and triglyceride levels in CF1 mice at 8 mg/kg/day after 16 days of treatment. Compounds 4, 5,and 17 lowered serum cholesterol levels 63%, 58%, and 42%, respectively, after 16 days at 8 mg/kg/day i.p.. These agents reduced the serum triglyceride levels by 33%, 37%, and 54%, respectively. In Sprague-Dawley rats these compounds also demonstrated significant serum lipid lowering effects by decreasing both serum cholesterol and triglyceride levels after 14 days of oral drug administration at 8 mg/kg/day. Compound 17 reduced the rat aorta cholesterol levels by 37%, triglyceride levels by 50%, and neutral lipid levels by 34% after 14 days of oral administration. These compounds lowered the chylomicron, VLDL, and LDL cholesterol and triglyceride levels while elevating the HDL cholesterol levels significantly. In hyperlipidemic rodents, these analogs also demonstrated significant serum lipid lowering effects but were less active than in normolipidemic rodents. The activities of some enzymes, such as mouse hepatic acetyl CoA synthetase, HMG CoA reductase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase, were significantly reduced by these compounds.
Mannich Reaction of Carbonyl Compounds via Boron Enolates and N,N,N',N'-Tetramethyldiaminomethane
Nolen, Ernest G.,Allocco, Andrea,Vitarius, Jim,McSorley, Karen
, p. 1532 - 1533 (2007/10/02)
A variety of carbonyl compounds undergo N,N-dimethylaminomethylation in moderate to good yields by the Mannich reaction involving boron enolates and N,N,N',N'-tetramethyldiaminomethane in dichloromethane.
