158628-72-9

Usage

Uses

Used in Pharmaceutical Applications:
1'-(1-(3-iodobenzyl)--4-hydroxypiperidin-3-yl)-3,4-dihydrospiro(naphthalene-1(2H),4'-piperidine) is used as a potential pharmaceutical agent for [application reason] due to its unique structural features and potential interactions with biological systems.
Used in Chemical Research:
In the field of chemical research, 1'-(1-(3-iodobenzyl)--4-hydroxypiperidin-3-yl)-3,4-dihydrospiro(naphthalene-1(2H),4'-piperidine) is used as a subject of study for [application reason] because of its complex structure and the possibility of discovering new properties and applications through detailed analysis and experimentation.

Upstream product

• 49617-83-6 m-Iodobenzyl bromide 
• 694-05-3 1,2,3,6-tetrahydropyridine 
• 161157-50-2 tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate 
• 85838-94-4 N-Boc-1,2,3,6-tetrahydropyridine 

Relevant academic research and scientific papers

Spirovesamicols

The compounds are vesamicol (hydroxylated phencyclidine (PCP) isomer trans-2-(4-phenyl-piperidino)cyclohexanol) derivatives with anticholinergic properties termed herein "spirovesamicols" which are spirofused piperidines. The compounds bind to the vesamicol receptor, a site on the cholinergic synaptic vesicle, which is associated with the vesicular transporter of acetylcholine.

Spirovesamicols: Conformationally restricted analogs of 2-(4- phenylpiperidino)cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function

In an effort to develop selective inhibitors of vesicular acetylcholine storage, we have synthesized a series of semirigid vesamicol receptor ligands based on the structure of 2-(4-phenylpiperidino)-cyclohexanol (vesamicol, AH5183, 1). In these compounds, the planes of the phenyl and piperidyl moieties of the parent ligand 1 are held at right angles by vinyl, ethylene, and propylene bridges to form N-substituted derivatives of spiro[indene- 1,4'-piperidine], 2,3-dihydrospiro[indene-1,4'-piperidine], and 3,4- dihydrospiro[naphthalene-1(2H),4'-piperidine], respectively. Preliminary evaluation of these compounds in electric organ synaptic vesicles revealed several potent vesamicol receptor ligands, such as 1'-(2-hydroxy-1,2,3,4- tetrahydronaphth-3-yl)spiro[1H-indene-1,4'-piperidine] (11b) and 1'-(2- hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro[2-bromo-1H-indene-1,4'- piperidine] (14), which display subnanomolar affinity for this receptor. In general, the vinyl and ethylene bridges yielded the most potent analogs while the propylene-bridged analogs were among the least potent compounds. The increased rigidity of these spiro-fused compounds, relative to the corresponding simple 4-phenylpiperidine derivatives of vesamicol, is expected to confer greater selectivity for the vesamicol receptor.