1026-88-6

Usage

Uses

Used in Organic Synthesis:
1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is used as an intermediate in the synthesis of various organic compounds for [application reason] its structural versatility and reactivity.
Used in Medicinal Chemistry:
1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is used as a building block in the development of new pharmaceuticals for [application reason] its potential pharmacological properties and structural features that may contribute to the desired biological activity.
Used in Pharmaceutical Production:
1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is used as a precursor in the production of various pharmaceuticals and research chemicals for [application reason] its ability to be further modified or reacted to create therapeutically relevant molecules.
Used in Research and Development:
1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is used in research and development for [application reason] its potential to be explored for novel applications and properties, which may lead to the discovery of new drugs or chemical processes.

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

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

Relevant academic research and scientific papers

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 of mannich bases by two different methods and evaluation of their acetylcholine esterase and carbonic anhydrase inhibitory activities

Background: Mannich bases are an important compounds in medicinal chemistry. They have wide range of biological activities including carbonic anhydrase (CA) inhibitory and acetylcholine esterase inhibitory (AChE) activities. Objective: It was aimed to synthesize Mannich bases, 1-aryl-3-(morpholin-4-yl/piperidin-1-yl)-1- propanone hydrochloride, by microwave irradiation and conventional heating methods to compare the methods in terms of reaction times and yields and to investigate their inhibitory effects on AChE enzyme and CA isoenzymes. Method: Mannich bases were synthesized using conventional heating and microwave irradiation methods under different reaction conditions. Inhibitory effects of the compounds on CA isoenzymes and AChE were evaluated according to literature procedure. Results: IC50 and Ki values of the compounds were evaluated against hCA I, II and AChE. The compounds had more potent or equal Ki values with the references used. Conclusion: This study makes an important contribution to the Mannich base library in terms of synthetic strategy. According to IC50 or Ki values the compounds 6 in Series A with morpholine and and 15 in Series B with piperidine towards both hCA I and/or II isoenzymes and the compounds 4 in Series A and 11, 13, 14, 15, 16, and 18 in Series B towards AChE seemed the leader compounds of the study.

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.

Evaluation of alkylating and intercalating properties of mannich bases for cytotoxic activity

A series of new "hybrid compounds", Mannich base derivatives of planar polycyclic/heterocyclic starting materials, was designed and synthesized. The structures of the compounds were confirmed by spectroscopic methods and elemental analysis. Cytotoxicity of compounds was investigated in three cancer cell lines (PC3, HeLa, and MCF7) and one non-tumoral cell line (293 HEK). We tested the DNA-intercalating capability of the molecules by ethidium bromide (EtBr) fluorescence displacement experiment. Compounds' alkylation potency was investigated via in vitro incubation test using 2-mercaptoethanol, a biomimetic nucleophile. The five of the compounds (7s, 9d, 10b, 11b, 12c) are reported for first time in the literature. Our results suggest that compound 9d has a biological activity close to the reference compound doxorubicin, an intercalating agent in clinical use.

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.

Alkylation of 5-Substituted 1H-Tetrazoles with Mannich Bases Derived from Acetophenone

Alkylation of 5-substituted 1H-tetrazoles with N-piperidinium chloride and N-piperidinium chloride in dimethylformamide at 150 deg C results in formation of one of the two possible N1- or N2-isomers.