13603-25-3Relevant articles and documents
Probing the proposed phenyl-A region of the sigma-1 receptor.
Ablordeppey, Seth Y,Fischer, James B,Law,Glennon, Richard A
, p. 2759 - 2765 (2002)
The proposed phenyl-A region of sigma (sigma) receptors accommodates several structural features. In this study we explored the possibility that appropriate structural features located at the phenyl-A region of sigma receptor sites could lead to more potent and selective agents for the sigma receptor subtypes. By keeping the phenyl-B substituent as the optimum omega-phenylpentyl moiety, and varying substituents in the phenyl-A region, we have observed changes in binding potency and selectivity at the sigma receptor subtypes. SAR for the binding of these compounds at sigma-2 sites was also examined.
An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups
Subota, Andrii I.,Ryabukhin, Sergey V.,Gorlova, Alina O.,Grygorenko, Oleksandr O.,Volochnyuk, Dmitriy M.
, p. 61 - 66 (2019/05/29)
An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups was proposed. The method was based on the DAST-mediated nucleophilic fluorination of easily available 2-bromopyridin-3-yl alcohols and ketones affording 2-bromo-3-(1-fluoroalkyl)pyridines and 2-bromo-3-(1,1-difluoroalkyl)pyridines, respectively, followed by catalytic hydrogenation. The hydrogenation step was studied with common heterogeneous Pd-, Pt-, and Rh-based catalyst. It was found that in the case of fluoroalkyl derivatives, the pyridine core reduction was accompanied by hydrodefluorination, which became a limitation of the strategy. Nevertheless, the method worked well with 1,1-difluoroalkyl derivatives
Approach to 3-(Cyclo)alkylpiperidines through 'sp3-sp3 via sp2-sp3' Coupling
Subota, Andrii I.,Grygorenko, Oleksandr O.,Valter, Yevheniia B.,Tairov, Maxim A.,Artamonov, Oleksiy S.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.
supporting information, p. 408 - 411 (2015/02/19)
The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp3-sp3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp3-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.
