5782-90-1

Usage

Chemical classification

1,2,3,4-Tetrahydro-9-(1-piperidinyl)acridine is a heterocyclic organic compound.

Derivative

It is a derivative of acridine.

Structural components

It contains a piperidine ring.

Pharmacological applications

The compound has potential pharmacological applications.

Serotonin receptor agonist

It has been studied for its potential as a serotonin receptor agonist.

Implications in central nervous system disorders

May have implications in the treatment of disorders such as depression and anxiety.

Anticonvulsant properties

Exhibits moderate anticonvulsant properties in animal models.

Analgesic properties

Exhibits analgesic properties in animal models.

Potential therapeutic uses

Suggesting potential use as a therapeutic agent for epilepsy and pain management.

Further research needed

More research is needed to fully understand the pharmacological properties and potential applications of 1,2,3,4-Tetrahydro-9-(1-piperidinyl)acridine.

InChI:InChI=1/C18H22N2/c1-6-12-20(13-7-1)18-14-8-2-4-10-16(14)19-17-11-5-3-9-15(17)18/h2,4,8,10H,1,3,5-7,9,11-13H2

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 321-64-2 tacrin 
• 13161-85-8 1,2,3,4,9,10-hexahydroacridin-9-one 
• 5396-30-5 9-chloro-1,2,3,4-tetrahydroacridine 
• 110-89-4 piperidine 
• 79000-43-4 9-phenoxy-1,2,3,4-tetrahydro-acridine 

Relevant academic research and scientific papers

Tacrine-O-protected phenolics heterodimers as multitarget-directed ligands against Alzheimer's disease: Selective subnanomolar BuChE inhibitors

Concerned by the devastating effects of Alzheimer's disease, and the lack of effective drugs, we have carried out the design of a series of tacrine-phenolic heterodimers in order to tackle the multifactorial nature of the disease. Hybridization of both pharmacophores involved the modification of the nature (imino, amino, ether) and the length of the tether, together with the type (hydroxy, methoxy, benzyloxy), number and position of the substituents on the aromatic residue. Title compounds were found to be strong and selective inhibitors of human BuChE (from low nanomolar to subnanomolar range), an enzyme that becomes crucial in the more advanced stages of the disease. The lead compound, bearing an ether-type tether, had an IC50 value of 0.52 nM against human BuChE, and a selectivity index of 323, with an 85-fold increase of activity compared to parent tacrine; key interactions were analysed using molecular modelling. Moreover, it also inhibited the self-aggregation of Aβ42, lacking neurotoxicity up to 5 μM concentration, and showed neuroprotective activity in primary rat neurons in a serum and K+ deprivation model, widely employed for reproducing neuronal injury and senescence. Moreover, low hepatoxicity effects and complete stability under physiological conditions were found for that compound. So, overall, our lead compound can be considered as a promising multitarget-directed ligand against Alzheimer's disease, and a good candidate for developing new drugs.

THE SYNTHESIS OF 9-(1-AZETIDINYL)-1,2,3,4-TETRAHYDROACRIDINE

Synthesis of analogue (2) of tacrine is described in which the primary amino group is replaced by the azetidine moiety.The synthesis was accomplished in two steps from the acridinone derivative 10.This involved conversion of 10 to triflate 11, followed by treatment with azetidine to give the target compound 2.