23702-98-9Relevant articles and documents
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 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
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.