224449-69-8

Basic information

• Product Name: 4-(4-cyclopentyloxyphenyl)-1,2,3,6-tetrahydropyridine
• Synonyms: 4-(4-cyclopentyloxyphenyl)-1,2,3,6-tetrahydropyridine
• CAS NO: 224449-69-8
• Molecular Weight: 243.349
• Mol File: 224449-69-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-(4-cyclopentyloxyphenyl)-1,2,3,6-tetrahydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-cyclopentyloxyphenyl)-1,2,3,6-tetrahydropyridine(224449-69-8)
• EPA Substance Registry System: 4-(4-cyclopentyloxyphenyl)-1,2,3,6-tetrahydropyridine(224449-69-8)

Safety Data

• Hazardous Substances Data: 224449-69-8(Hazardous Substances Data)

Upstream product

• 224449-67-6 N-tert-butoxycarbonyl-(4-(4-cyclopentyloxy)phenyl)-4-piperidinol 
• 30752-30-8 1-bromo-4-(cyclopentyloxy) benzene 
• 106-41-2 4-bromo-phenol 
• 137-43-9 Cyclopentyl bromide 

Downstream Products

• 224449-71-2 4-(4-cyclopentyloxyphenyl)piperidine 

Relevant articles and documents

Synthesis and biological evaluation of new 4-arylpiperidines and 4-aryl-4-piperidinols: dual Na+ and Ca2+ channel blockers with reduced affinity for dopamine D2 receptors

A series of novel 4-arylpiperidines and 4-aryl-4-piperidinols (2a-f, 3a-f and 4a-f) was synthesized and evaluated for blocking effects on both neuronal Na+ and T-type Ca2+ channels and binding affinity for dopamine D2 receptors. Most of the compounds blockaded both ion channels with potency greater than or equal to flunarizine 1a which was adopted as a reference standard. In addition, these compounds had significantly reduced affinity for dopamine D2 receptors which is common in this class of structure. Compounds 2a-f, 3a-f and 4a-f exhibited potent anticonvulsant effects following systemic (ip) administration on audiogenic seizures in DBA/2 mice, indicating their excellent brain permeability. The neuroprotective activity of 2a, 3a and 4a was also assessed in a transient middle cerebral artery occlusion (MCAO) model. These compounds significantly reduced neuronal damage without affecting ischemic hyperthemia, while flunarizine 1a produced only minor reductions. In particular, 4a had 1.7-fold the potency in this MCAO method but only 1/20 the affinity for dopamine D2 receptor of 1a. The superposition of 2a, 3a and 4a on the basis of analyses of systematic conformation and similar structure has revealed that the cinnamyl, phenacyl and phenoxypropanol groups are likely to be structurally and biologically equivalent. Moreover, the superposition of 2a and 2f shows that diphenyl ether and biphenyl groups occupy a similar space, suggesting that both groups act as a bioisostere for the blockade of ion channels; however, this is not the case for dopamine D2 receptors since only biphenyl compounds such as 2f had high affinitity similar to flunarizine 1a. Compound 4a (SUN N5030) has a good pharmacological profile and may be useful in the alleviation and treatment of ischemic diseases. Copyright