802874-67-5

Upstream product

• 177-11-7 4,4-ethylenedioxy-piperidine 
• 824-94-2 p-methoxybenzyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 905986-94-9 1-[(4-methoxyphenyl)methyl]piperidin-4-one 
• 562824-88-8 N-[1-(4-methoxy-benzyl)-piperidin-4-ylidene]-N'-(2-nitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

18F-Labeled 1,4-Dioxa-8-azaspiro[4.5]decane Derivative: Synthesis and Biological Evaluation of a σ1 Receptor Radioligand with Low Lipophilicity as Potent Tumor Imaging Agent

We report the syntheses and evaluation of series of novel piperidine compounds with low lipophilicity as σ1 receptor ligands. 8-(4-(2-Fluoroethoxy)benzyl)-1,4-dioxa-8-azaspiro[4.5]decane (5a) possessed high affinity (Ki = 5.4 ± 0.4 nM) for σ1 receptors and selectivity for σ2 receptors (30-fold) and the vesicular acetylcholine transporter (1404-fold). [18F]5a was prepared using a one-pot, two-step labeling procedure in an automated synthesis module, with a radiochemical purity of >95%, and a specific activity of 25-45 GBq/μmol. Cellular association, biodistribution, and autoradiography with blocking experiments indicated specific binding of [18F]5a to σ1 receptors in vitro and in vivo. Small animal positron emission tomography (PET) imaging using mouse tumor xenograft models demonstrated a high accumulation in human carcinoma and melanoma. Treatment with haloperidol significantly reduced the accumulation of the radiotracer in tumors. These findings suggest that radiotracer with suitable lipophilicity and appropriate affinity for σ1 receptors could be used for tumor imaging.

Spiro[1,2,4-benzotriazine-3(4H),4′-(1′-substituted)piperidines] and related compounds as ligands for sigma receptors

As analogues of some conformationally restricted spiropiperidine derivatives which are endowed with high affinity for σ1 receptor, a set of 16 spiro[1,2,4-benzotriazine-3(4H),4′-(1′-substituted)piperidines] and congeneric compounds was prepared and tested for affinity to σ1 receptor subtype. All N-arylalkyl substituted derivatives exhibited high affinity for the relevant receptor, with Ki in the low nanomolar range. Affinity for σ2 subtype (assayed only for a few representative compounds) was from one to three order of magnitude lower. Spiro[1,2,4-benzotriazine-3(4H),4′-(1′-benzyl)piperidine] (2), with a ratio Kiσ2/Kiσ1=7000 should represent the most selective σ1 ligand so far described.