475095-03-5Relevant academic research and scientific papers
Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules
Howell, Jennifer M.,Feng, Kaibo,Clark, Joseph R.,Trzepkowski, Louis J.,White, M. Christina
, p. 14590 - 14593 (2015/12/08)
Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.
General and efficient synthetic approach to novel tricyclic spiroketones
Chu, Guo-Hua,Le Bourdonnec, Bertrand,Gu, Minghua,Saeui, Christopher T.,Dolle, Roland E.
experimental part, p. 5161 - 5167 (2009/12/09)
A general and efficient synthetic approach to tricyclic spiroketones of interest as useful scaffolds in drug discovery was developed. Starting from commercially available benzyl 4-oxo-1-piperidinecarboxylate (5), spirocyclic tetralone 4, spirocyclic indanone 14, and spirocyclic benzocycloheptanone 15 were synthesized via six reaction steps in excellent overall yield.
Melanocortin subtype 4 receptor agonists: Structure-activity relationships about the 4-alkyl piperidine core
Sebhat, Iyassu K.,Lai, Yingjie,Barakat, Khaled,Ye, Zhixiong,Tang, Rui,Kalyani, Rubana N.,Vongs, Aurawan,MacNeil, Tanya,Weinberg, David H.,Cabello, M. Angeles,Maroto, Marta,Teran, Ana,Fong, Tung M.,Van der Ploeg, Lex H.T.,Patchett, Arthur A.,Nargund, Ravi P.
, p. 5720 - 5723 (2008/04/03)
SAR about the piperidine core in a series of MC4R agonists is described. A number of alkyl substituents that furnish compounds with good affinity and functional potency are reported.
SPIROCYCLIC HETEROCYCLIC DERIVATIVES AND METHODS OF THEIR USE
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Page/Page column 168; 441-442, (2008/06/13)
Spirocyclic heterocyclic derivatives, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the spirocyclic heterocyclic derivatives are ligands of the δ opioid receptor and may be useful, inter alia, for treating and/or preventing pain, anxiety, gastrointestinal disorders, and other δ opioid receptor-mediated conditions.
Design and pharmacology of N-[(3R)-1,2,3,4-tetrahydroisoquinolinium-3-ylcarbonyl]-(1R)-1- (4-chlorobenzyl)-2-[4-cyclohexyl-4-(1H-1,2,4-triazol-1-ylmethyl) piperidin-1-yl]-2-oxoethylamine (1), a potent, selective, melanocortin subtype-4 receptor agonist
Sebhat, Iyassu K.,Martin, William J.,Ye, Zhixiong,Barakat, Khaled,Mosley, Ralph T.,Johnston, David B. R.,Bakshi, Raman,Palucki, Brenda,Weinberg, David H.,MacNeil, Tanya,Kalyani, Rubana N.,Tang, Rui,Stearns, Ralph A.,Miller, Randy R.,Tamvakopoulos, Constantin,Strack, Alison M.,McGowan, Erin,Cashen, Doreen E.,Drisko, Jennifer E.,Hom, Gary J.,Howard, Andrew D.,MacIntyre, D. Euan,Van der Ploeg, Lex H. T.,Patchett, Arthur A.,Nargund, Ravi P.
, p. 4589 - 4593 (2007/10/03)
Synthetic and natural peptides that act as nonselective melanocortin receptor agonists have been found to be anorexigenic and to stimulate erectile activity. We report the design and development of 1, a potent, selective (1184-fold vs MC3R, 350-fold vs MC5R), small-molecule agonist of the MC4 receptor. Pharmacological testing confirms the food intake lowering effects of MC4R agonism and suggests another role for the receptor in the stimulation of erectile activity.
