1026-88-6

Basic information

• Product Name: 1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one
• Synonyms: 1-(4-Methoxyphenyl)-3-(piperidin-1-yl)propan-1-one; 1-Propanone, 1-(4-methoxyphenyl)-3-(1-piperidinyl)-
• CAS NO: 1026-88-6
• Molecular Formula: C₁₅H₂₁NO₂*ClH
• Molecular Weight: 247.3327
• Mol File: 1026-88-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 385°C at 760 mmHg
• Flash Point: 186.6°C
• Density: 1.052g/cm³
• Vapor Pressure: 3.94E-06mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one(1026-88-6)
• EPA Substance Registry System: 1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one(1026-88-6)

Safety Data

• Hazardous Substances Data: 1026-88-6(Hazardous Substances Data)

Usage

General Description

1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is a chemical compound with the molecular formula C14H19NO2. It is a ketone derivative, consisting of a phenyl ring substituted with a methoxy group and a piperidine ring attached to a propanone moiety. 1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one has potential applications in the field of organic synthesis and medicinal chemistry, and it may have pharmacological properties due to its structural features. Additionally, it could be used as a precursor in the production of various pharmaceuticals and research chemicals. The compound's precise properties and applications may be subject to further research and development.

Upstream product

• 50-00-0 formaldehyd 
• 6091-44-7 piperidine hydrochloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 123612-85-1 C₃₀H₄₂N₂O₂ 
• 173309-46-1 3-[5-(3,4-Dimethoxy-phenyl)-tetrazol-2-yl]-1-(4-methoxy-phenyl)-propan-1-one 
• 42528-76-7 1-(4-hydroxyphenyl)-3-(piperidin-1-yl)propan-1-one 

Relevant articles and documents

Identification of dual Sigma1 receptor modulators/acetylcholinesterase inhibitors with antioxidant and neurotrophic properties, as neuroprotective agents

In this manuscript we report on the design, synthesis and evaluation of dual Sigma 1 Receptor (S1R) modulators/Acetylcholinesterase (AChE) inhibitors endowed with antioxidant and neurotrophic properties, potentially able to counteract neurodegeneration. The compounds based on arylalkylaminoketone scaffold integrate the pharmacophoric elements of RRC-33, a S1R modulator developed by us, donepezil, a well-known AChE inhibitor, and curcumin, a natural antioxidant compound with neuroprotective properties. A small library of compounds was synthesized and preliminary in vitro screening performed. Some compounds showed good S1R binding affinity, selectivity towards S2R and N-Methyl-D-Aspartate (NMDA) receptor, AChE relevant inhibiting activity and are potentially able to bypass the BBB, as predicted by the in silico study. For the hits 10 and 20, the antioxidant profile was assessed in SH-SY5Y human neuroblastoma cell lines by evaluating their protective effect against H2O2 cytotoxicity and reactive oxygen species (ROS) production. Tested compounds resulted effective in decreasing ROS production, thus ameliorating the cellular survival. Moreover, compounds 10 and 20 showed to be effective in promoting the neurite elongation of Dorsal Root Ganglia (DRG), thus demonstrating a promising neurotrophic activity. Of note, the tested compounds did not show any cytotoxic effect at the concentration assayed. Relying on these encouraging results, both compounds will undergo a structure optimization program for the development of therapeutic candidates for neurodegenerative diseases treatment.

Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones

A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human oral malignant versus nonmalignant cells. The compound induced apoptosis in HSC-2 oral squamous cell carcinoma cells, but not in human gingival fibroblast. Chemical modifications of this lead are thus necessary to further investigate it as a drug candidate and to obtain compounds with a better activity profile.

Synthesis of new N,N′-bis[1-aryl-3-(piperidine-1-yl)propylidene] hydrazine dihydrochlorides and evaluation of their cytotoxicity against human hepatoma and breast cancer cells

N,N0-Bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides were synthesized by the reaction of 2 mols of 1-aryl-3-(piperidine-1-yl)-1- propanone hydrochlorides with 1 mol of hydrazine hydrate. Aryl part was C 6H5 (P1), 4-CH3C6H4 (P2), 4-CH3OC6H4 (P3), 4-HOC6H 4 (P4), 4-ClC6H4 (P5), 3-CH3OC 6H4 (P6), 4-FC6H4 (P7) and 4-BrC6H4 (P8). Except P1, all compounds were reported for the first time. The chemical structures were confirmed by UV, 1H NMR, 13C NMR and HRMS spectra. P1, P2, P7 and P8 against human hepatoma (Huh7) cells and P1, P2, P4, P5, P6, P7 and P8 against breast cancer (T47D) cells have shown cytotoxicity. P1, P2 and P7 had more potent cytotoxicity against Huh7 cells than the reference compound 5-FU, whereas only P2 was more potent than the 5-FU against T47D cells. Representative compound P7 inhibited the mitochondrial respiration at 144, 264 and 424 mM concentrations dose-dependantly in liver homogenates. The results suggest that P1, P2, P7 and P8 may serve as model compounds for further synthetic studies.