4476-25-9Relevant academic research and scientific papers
Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites
Mbofana, Curren T.,Chong, Eugene,Lawniczak, James,Sanford, Melanie S.
, p. 4258 - 4261 (2016/09/09)
We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
Phenylindole derivatives as 5-HT2A receptor ligands
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, (2008/06/13)
A class of tryptamine analogues bearing an optionally substituted phenyl nucleus at the 2-position are selective antagonists of the human 5-HT2Areceptor and are therefore useful as pharmaceutical agents, especially in the treatment and/or preve
Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents
Huang,Hall
, p. 281 - 290 (2007/10/03)
A number of N-substituted β-alkylaminophenone derivatives including two (α- and two γ-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 μM.
Efficient asymmetric hydrogenation of β- and γ-amino ketone derivatives leading to practical synthesis of fluoxetine and eprozinol
Sakuraba,Achiwa
, p. 748 - 753 (2007/10/02)
N-(Methylcarbamoyl)-4-(dicyclohexylphosphino)-2-[(diphenylphosphino)me thyl]pyrrolidine (MCCPM)- and N-(tert-butoxycarbonyl)-4-(dicyclohexylphosphino)-2-[(diphenylphosphin o)methyl]pyrrolidine (BCPM)-rhodium(I) complexes were efficient catalysts for asymmetric hydrogenations of β- and γ-amino ketone hydrochloride derivatives. Utilizing this methodology, we have developed efficient syntheses of fluoxetine and eprozinol from intermediate optically active amino alcohols.
Synthesis and Antiarrhythmic Activity of cis-2,6-Dimethyl-α,α-diaryl-1-piperidinebutanols
Hoefle, M. L.,Blouin, L. T.,Fleming, R. W.,Hastings, S.,Hinkley, J. M.,et al.
, p. 12 - 19 (2007/10/02)
A series of α,α-diaryl-1-piperidinebutanols was evaluated for antiarrhythmic activity in the coronary ligated dog model.Structure-activity relationship studies indicated that the 2,6-dimethylpiperidine group yielded compounds with the best antiarrhythmic
