24157-18-4

Usage

Functional Groups

Tertiary amine: Contains a nitrogen atom bonded to three carbon atoms.
Piperidine ring: A heterocyclic ring consisting of five carbon atoms and one nitrogen atom.
Benzyl group: A phenyl group (C6H5) attached to a methylene (CH2) group.

Role

Intermediate in Synthesis: Used in the production of various pharmaceuticals and organic compounds.
Building Block: Essential in the creation of new drugs and research chemicals.

Applications

Pharmaceutical Industry: Employed in the synthesis of drugs with potential medicinal properties.
Medicinal Chemistry: Potential applications in drug discovery due to its unique structure and properties.

Properties

Chemical Stability: Generally stable under typical laboratory conditions.
Solubility: May vary depending on the specific compound being synthesized or researched.
Reactivity: Reacts with other chemicals to form desired products in synthesis reactions.

Potential Uses

Therapeutic Agents: Could be incorporated into drugs targeting specific biological pathways or diseases.
Research Chemicals: Utilized as a tool for investigating biological systems or developing new treatment modalities.

Structural Characteristics

Contains a piperidine ring fused to a propylamine chain with a benzyl substituent on the piperidine ring.

Synthetic Importance

Plays a crucial role as an intermediate, facilitating the construction of more complex molecules.

Biological Activity

May exhibit pharmacological effects or interactions with biological targets, depending on its specific structure and functional groups.

Regulatory Considerations

Subject to regulations governing the handling, transportation, and usage of chemical substances, particularly those intended for pharmaceutical applications.

Upstream product

• 4608-82-6 3-(4-benzylpiperidin-1-yl)propanenitrile 
• 31252-42-3 4-benzylpyperidine 
• 198895-29-3 2-(3-(4-benzylpiperidin-1-yl)propyl)isoindoline-1,3-dione 

Downstream Products

• 304858-97-7 N-benzyl-3-(4-benzyl-1-piperidinyl)-1-propaneamine 

Relevant academic research and scientific papers

Novel Sigma Receptor Ligand-Nitric Oxide Photodonors: Molecular Hybrids for Double-Targeted Antiproliferative Effect

This contribution reports the synthesis and evaluation of novel hybrid compounds that conjugate a sigma (σ) receptor pharmacophore and a nitric oxide (NO) photodonor. All compounds preserve their capability to generate NO under visible light and possess overall σ receptor nanomolar affinity, with one of them (8b) exhibiting remarkable σ2 receptor selectivity. Compounds 8b, 11a, and 11b were tested on tumorigenic MCF-7 and A2058 cells expressing high levels of σ2 and σ1 receptor, respectively. Considerable loss of cell viability was detected under light excitation, while negligible effects in the dark were detected. Moreover, they did not show any significant cytotoxicity in the dark or under irradiation on nontumorigenic NCTC-2544 keratinocytes. NO-induced reduction of cellular viability was demonstrated by in-cell NO detection and total nitrite estimation. For the first time, a combination of σ receptor moieties and a NO photodonor is reported, providing distinctive ligands potentially useful for cancer management.

Synthesis and evaluation of antiproliferative activity of novel quinazolin-4(3H)-one derivatives

Two series of novel quinazolin-4(3H)-one derivatives (10a–g and 11a–g) have been synthesized and evaluated for their in vitro antiproliferative activity against human HeLa, MIAPACA, MDA-MB-231, and IMR-31 cancer cell lines. The synthesized compounds were characterized by spectral (Fourier transform infrared, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, high-resolution mass spectra) methods. Among them, compounds 11e and 11g exhibited potent in vitro antiproliferative activity with GI50 values 0.02, less than 0.01 μM against MIAPACA human cancer cell line. Significantly, compounds 10a, 10b, 10c, 10g, 11b, 11c, 11d, 11e, 11f showed activity with GI50 values ranging from 0.1 to 0.87 μM against human cancer cell lines MIAPACA, MDA-MB-231, and IMR-31. We have explored the probable binding mode and key active site interactions in HDAC8 and EHMT2 proteins. The docking results are complementary to the experimental results.

Synthesis, biological evaluation and molecular docking study of novel piperidine and piperazine derivatives as multi-targeted agents to treat Alzheimer's disease

Development of Multi-Target Directed Ligands (MTDLs) has emerged as a promising approach for targeting complex etiology of Alzheimer's disease (AD). Following this approach, a new series of N′-(4-benzylpiperidin-/piperazin-/benzhydrylpiperazin-1-yl)alkylamine derivatives were designed, synthesized and biologically evaluated as inhibitors of cholinesterases (ChEs), amyloid-beta (Aβ) self aggregation and also for their radical scavenging activity. The in vitro studies showed that the majority of synthesized derivatives strongly inhibited acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) with IC50 values in the low-nanomolar range, and were clearly more potent than the reference compound donepezil in this regard. Among them, inhibitors 5h and 5k, strongly inhibited AChE, with IC50 value of 6.83 nM and 2.13 nM, respectively, and particularly, compound 5k was found to be highly selective for AChE (～38-fold). Moreover, both kinetic analysis of AChE inhibition and the docking study suggested that 5k binds simultaneously to catalytic active site and peripheral anionic site of AChE. Besides, these compounds also exhibited greater ability to inhibit self-induced Aβ1-42 aggregation at 25 μM with percentage inhibition from ～54% to 89% and specially compound 5k provided highest inhibition (88.81%). Also, the derivatives containing methoxy and hydroxy groups showed potent oxygen radical absorbance capacity (ORAC) ranging from 2.2- to 4.4-fold of the Trolox value. Furthermore, results of ADMET studies suggested that all compounds exhibited appropriate drug like properties. Taken together, these results suggest that 5k might be a promising lead compound for further AD drug development.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

CCR3 antagonists: a potential new therapy for the treatment of asthma. Discovery and structure-activity relationships.

CCR3 antagonist leads with IC(50) values in the microM range were converted into low nM binding compounds that displayed in vitro inhibition of human eosinophil chemotaxis induced by human eotaxin. In particular, 4-benzylpiperidin-1-yl-n-propylureas and erythro-3-(4-benzyl-2-(alpha-hydroxyalkyl)piperidin-1-yl)-n-propylureas (obtained via Beak reaction of N-BOC-4-benzylpiperidine) exhibited single digit nanomolar IC(50) values for CCR3.

CYCLIC AMIDE COMPOUNDS, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF

A compound of the formula: wherein R1 is a hydrocarbon group, R2 is a hydrocarbon group having 2 or more carbon atoms, where R1 and R2 may in combination form, together with an adjacent nitrogen atom, a ring optionally having a substituent or substituents, R3 is a hydrocarbon group optionally having a substituent or substituents or a heterocyclic group optionally having a substituent or substituents, R4 is a hydrogen atom, a hydrocarbon group, a heterocyclic group and the like, E is a divalent chain hydrocarbon group and the like, G is CO or SO2, J is a nitrogen atom, a methine group and the like, and Q and R are each a divalent chain C1-3 hydrocarbon group and the like, and a salt thereof show a superior CCR5 antagonistic activity and are useful as agents for the prophylaxis or treatment of HIV infection of human peripheral blood mononuclear cells, particularly AIDS.

Subtype-selective NMDA receptor ligands and the use thereof

The invention relates to subtype-selective NMDA receptor ligands and the use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neuro-degenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, Parkinson's disease, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.