339549-67-6Relevant academic research and scientific papers
Enantiopure methoxetamine stereoisomers: chiral resolution, conformational analysis, UV-circular dichroism spectroscopy and electronic circular dichroism
Lee, Kun Won,Hassan, Ahmed H. E.,Jeong, Youngdo,Yoon, Seolmin,Kim, Seung-Hwan,Lee, Cheol Jung,Jeon, Hye Rim,Chang, Suk Woo,Kim, Ji-Young,Jang, Dae Sik,Kim, Hee Jin,Cheong, Jae Hoon,Lee, Yong Sup
, p. 4354 - 4364 (2021/03/15)
The chiral molecule, methoxetamine (MXE), demonstrated promising biological effects in management of treatment-resistant depression patients. To satisfy the need for a method capable of providing gram quantities of each enantiopure stereoisomer of MXE to enable advanced biological studies of enantiomers, a protocol was developed to access gram scale quantities of (R)- and (S)-MXE in the form of pharmaceutically acceptable HCl salts employingl-(?)-DTTA andd-(+)-DTTA ((?)-O,O′-di-p-toluoyl-l-tartaric acid and (+)-O,O′-di-p-toluoyl-d-tartaric acid, respectively) as two chiral resolving agents. In contrast to ketamine, the measured specific optical rotation and conformational analysis indicated that the most abundant conformers possess a common axial-methoxyphenyl conformation responsible for the conserved direction of optical rotation in both free base and HCl salt forms of the MXE stereoisomers. Finally, the absolute configuration was unambiguously assigned through matching experimental and calculated ECD spectra. This report offers a gateway to obtain gram scale amounts of enantiopure MXE stereoisomers needed to advance the current knowledge on MXE biology.
Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
Aretz, Christopher D.,Escobedo, Humberto,Cowen, Bryan J.
, p. 1880 - 1884 (2018/05/09)
Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.
Synthesis of methoxetamine, its metabolites and deuterium labelled analog as analytical standards and their HPLC and chiral capillary electrophoresis separation
Jurasek,Himl,Jurok,Hajkova,Vobinuskova,Rezanka,Kuchar
, p. 56691 - 56696 (2017/12/26)
Methoxetamine, a designer drug marketed as a replacement for the dissociative anaesthetic ketamine, has been associated with significant numbers of hospital related intoxications and deaths in Europe. The fast and user-friendly identification and quantification of methoxetamine and its metabolites is a key factor for successful treatment of intoxication. Therefore, we suggested a convenient preparation method which was used for the synthesis of methoxetamine, seven methoxetamine metabolites and a deuterium labelled derivative as analytical standards. Methoxetamine and normethoxetamine were used as starting materials for the preparation of O-demethylated and N-dealkylated metabolites. The multistep synthesis starts from commercially available compounds and offers good yields. Our prepared analytical standards were used for the confirmation of the suggested structure of methoxetamine metabolites in rat urine by LCMS. Capillary electrophoresis was used for the chiral separation of MXE and its metabolites using β-cyclodextrin, carboxymethylated β-cyclodextrin, and sulphated β-cyclodextrin as chiral selectors at various concentrations. Chiral separation was successful for four analytes. A mixture of MXE and its metabolites was subsequently analyzed under optimal conditions, i.e. when using 15 mmol L-1 β-cyclodextrin in 50 mmol L-1 phosphate buffer, pH 2.5. In this case, chiral separation was achieved for three analytes and all analytes were separated from each other.
Direct catalytic asymmetric three-component Kabachnik-fields reaction
Cheng, Xu,Goddard, Richard,Buth, Gernot,List, Benjamin
supporting information; experimental part, p. 5079 - 5081 (2009/03/11)
(Chemical Equation Presented) As mimics of α-amino acids, α-amino phosphonates have great promise as antibacterial and anti-HIV agents as well as protease inhibitors. Racemic α-branched aldehydes react, in the presence the new chiral phosphoric acid catalyst 1, directly with p-anisidine (PMPNH2) and a phosphite to furnish β-branched α-amino phosphonates highly diastereoselectively and enantioselectively. Anth = anthracenyl.
