72807-18-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(1H-Indol-3-ylmethyl)piperidin-4-amine is used as a potential therapeutic agent for neurological disorders and psychiatric conditions due to its ability to modulate neurotransmitter levels in the brain. Its impact on dopamine and serotonin suggests it may be beneficial in the treatment of mood disorders and addiction.
Used in Research and Development:
In the field of medicinal chemistry and neuroscience, 1-(1H-Indol-3-ylmethyl)piperidin-4-amine serves as a subject of ongoing research to further understand its mechanisms of action and to explore its potential applications in the development of new medications for various brain-related conditions.

InChI:InChI=1/C14H19N3/c15-12-5-7-17(8-6-12)10-11-9-16-14-4-2-1-3-13(11)14/h1-4,9,12,16H,5-8,10,15H2

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Discovery of Aminopiperidine Indoles That Activate the Guanine Nucleotide Exchange Factor SOS1 and Modulate RAS Signaling

Deregulated RAS activity, often the result of mutation, is implicated in approximately 30% of all human cancers. Despite this statistic, no clinically successful treatment for RAS-driven tumors has yet been developed. One approach for modulating RAS activity is to target and affect the activity of proteins that interact with RAS, such as the guanine nucleotide exchange factor (GEF) son of sevenless homologue 1 (SOS1). Here, we report on structure-activity relationships (SAR) in an indole series of compounds. Using structure-based design, we systematically explored substitution patterns on the indole nucleus, the pendant amino acid moiety, and the linker unit that connects these two fragments. Best-in-class compounds activate the nucleotide exchange process at submicromolar concentrations in vitro, increase levels of active RAS-GTP in HeLa cells, and elicit signaling changes in the mitogen-activated protein kinase-extracellular regulated kinase (MAPK-ERK) pathway, resulting in a decrease in pERK1/2T202/Y204 protein levels at higher compound concentrations.

Structure-Activity Relationship, Pharmacological Characterization, and Molecular Modeling of Noncompetitive Inhibitors of the Betaine/γ-Aminobutyric Acid Transporter 1 (BGT1)

N-(1-Benzyl-4-piperidinyl)-2,4-dichlorobenzamide 5 (BPDBA) is a noncompetitive inhibitor of the betaine/GABA transporter 1 (BGT1). We here report the synthesis and structure-activity relationship of 71 analogues. We identify 26m as a more soluble 2,4-Cl substituted 3-pyridine analogue with retained BGT1 activity and an improved off-target profile compared to 5. We performed radioligand-based uptake studies at chimeric constructs between BGT1 and GAT3, experiments with site-directed mutated transporters, and computational docking in a BGT1 homology model based on the newly determined X-ray crystal structure of the human serotonin transporter (hSERT). On the basis of these experiments, we propose a binding mode involving residues within TM10 in an allosteric site in BGT1 that corresponds to the allosteric binding pocket revealed by the hSERT crystal structure. Our study provides first insights into a proposed allosteric binding pocket in BGT1, which accommodates the binding site for a series of novel noncompetitive inhibitors.