23702-98-9Relevant academic research and scientific papers
Synthetic Cathinone Analogues Structurally Related to the Central Stimulant Methylphenidate as Dopamine Reuptake Inhibitors
Yadav-Samudrala, Barkha J.,Eltit, Jose M.,Glennon, Richard A.
, p. 4043 - 4050 (2019/09/07)
Synthetic cathinones are, primarily, stimulant drugs of abuse that act at monoamine transporters (e.g., the dopamine transporter or DAT) as releasing agents or as reuptake inhibitors. In the past few years, the emergence of >150 new synthetic cathinones has attracted considerable attention from medical and law enforcement communities. threo-Methylphenidate (tMP), used clinically for the treatment of ADHD and narcolepsy, is also a DAT reuptake inhibitor. tMP is somewhat structurally similar to abused cathinone stimulants, and the structure-activity relationships (SAR) of tMP have been well-defined. Hence, available tMP literature might assist in understanding the SAR of synthetic cathinones, about which less is known. In the present study, we synthesized and examined eight 2-benzoylpiperidine analogues (4, 6-12) to determine if tMP SAR might be applicable to cathinone SAR. The benzoylpiperidine analogues were evaluated in a competition assay using live-cell imaging against APP+ in HEK293 cells stably expressing hDAT and in cells coexpressing DAT and voltage-gated Ca2+ channels. All compounds were found to be DAT reuptake inhibitors, and a significant correlation was obtained between the potency of the benzoylpiperidines and tMP binding data (r = 0.91), suggesting that the SAR of tMP analogues might be directly applicable to certain synthetic cathinones as DAT reuptake inhibitors.
Concise and facile synthesis of (R,R)-dexmethylphenidate hydrochloride and its three stereoisomers
Li, Chunzheng,Ji, Yuanbo,Cao, Qing,Li, Jianqi,Li, Bonan
supporting information, p. 1301 - 1306 (2017/07/12)
A new and concise route is reported for the first time for the preparation of four stereoisomers of dexmethylphenidate hydrochloride starting from a single reactant, 2-benzyolpyridine, through an eight-step reaction process, which includes hydrogenation,
Concise preparation of a stable cyclic sulfamidate intermediate in the synthesis of a enantiopure chiral active diamine derivative
Rousseau, Jean-Francois,Chekroun, Isaac,Ferey, Vincent,Labrosse, Jean Robert
, p. 506 - 513 (2015/04/27)
A classical resolution was studied and developed from 2-benzoyl-pyridine in order to prepare SSR504734, a novel antipsychotic derivative. The key step of this route is the substitution of a sulfamidate derivative by a benzamide anion with complete inversi
Derivative of n-[phenyl(piperidin-2-yl)methyl]benzamide, the preparation method thereof and application of same in therapeutics
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Page/Page column 4, (2010/02/12)
Compound of general formula (I) in which A represents either a group of formula N—R1 in which R1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, a phenylalkyl group, an alkenyl group or an alkynyl group, or a group of
erythro-1-naphthyl-1-(2-piperidyl)methanol: Synthesis, resolution, NMR relative configuration, and VCD absolute configuration
Solladie-Cavallo,Marsol,Yaakoub,Azyat,Klein,Roje,Suteu,Freedman,Cao,Nafie
, p. 7308 - 7315 (2007/10/03)
The erythro isomer of 1-naphthyl-1-(2-piperidyl)methanol 4, an efficient chiral modifier for asymmetric heterogeneous hydrogenation, was obtained as the major isomer (95%) in two steps while the threo isomer can be obtained as the major isomer (67%) in th
Partial hydrogenation of substituted pyridines and quinolines: A crucial role of the reaction conditions
Solladié-Cavallo,Roje,Baram,?unji?
, p. 8501 - 8503 (2007/10/03)
Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group (1a-c and 2b,c) using PtO2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B1 and/or B2 (concentrated HCl or pure CF 3CO2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3) conditions A provide mixtures while under conditions B2 (pure CF 3CO2H) the benzene ring is cleanly hydrogenated leading to a pure product.
(Amidomethyl)nitrogen heterocyclic analgesics
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, (2008/06/13)
This invention relates to (amidomethyl)nitrogen heterocyclic and pyrrolidine compounds, pharmaceutical compositions containing them, methods of using such compounds and processes for making such compounds.
α-Lithioamine Synthetic Equivalents: Syntheses of Diastereoisomers from the Boc Piperidines
Beak, Peter,Lee, Won Koo
, p. 2578 - 2580 (2007/10/02)
The α'-lithiations and electrophilic substitutions of selected Boc piperidines provide single or separable diastereoisomeric 2-substituted, 2,4-disubstituted, and 2,4,6-trisubstituted Boc piperidines which are readily hydrolyzed to the substituted piperidines.
A NEW AND DIASTEREOSELECTIVE SYNTHESIS OF THREO-ARYL-2-PIPERIDYLMETHANOL DERIVATIVES
Delgado, Antonio,Hospital, Susana,Mauleon, David,Perez, Francesc
, p. 2017 - 2026 (2007/10/02)
A diastereoselective synthesis of threo-aryl-2-piperidyl- and aryl-1,2,3,6-tetrahydro-2-pyridylmethanol derivatives is described.The stereochemestry is controlled by intramolecularly assisted NaBH4 reduction of the intermediate carbamates 3.
α-Amino Carbanions. Preparation, Metalation, and Alkylation of Enamidines. Synthesis of Piperidine and Pyrrolidine Natural Products and Homologation of Carbonyl Compounds
Meyers, A. I.,Edwards, Philip D.,Bailey, Thomas R.,Jagdmann, G. Erik
, p. 1019 - 1026 (2007/10/02)
Saturated heterocycles, as their tert-butylformamidines, may be transformed into enamidines, by metalation-selenation-elimination.These enamidines are valuable precursors to 2-substituted, 2,4-disubstituted, and 2,4,6-trisubstituted pyrrolidines, piperidines, and perhydroazepines, prepared in a regiospecific manner.The method is demonstrated by the synthsesis of selenopsin A and the red fire ant venom.The use of acyclic enamidines is displayed as a homologation reagent which converts carbonyl compounds to higher alkyl derivatives.
