886-06-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Benzoylethyl)piperidinium chloride is used as a pharmaceutical agent for its cytotoxic effects against various cancer cell lines, such as Jurkat cells. Its ability to inhibit the growth and proliferation of cancer cells makes it a potential candidate for the development of anticancer drugs.
Used in Antimicrobial Applications:
In the field of antimicrobial agents, 1-(2-benzoylethyl)piperidinium chloride is utilized for its antibacterial and antifungal properties. It can be employed to combat various microbial infections, contributing to the development of new antibiotics and antifungal medications.

InChI:InChI=1/C14H19NO/c16-14(13-7-3-1-4-8-13)9-12-15-10-5-2-6-11-15/h1,3-4,7-8H,2,5-6,9-12H2

Upstream product

• 110-89-4 piperidine 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 50-00-0 formaldehyd 
• 6091-44-7 piperidine hydrochloride 
• 98-86-2 acetophenone 
• 646-06-0 1,3-DIOXOLANE 
• 110-88-3 1,3,5-Trioxan 
• 108-86-1 bromobenzene 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 108488-77-3 1-phenyl-3-piperidino-propane-1,2-dione-2-oxime 
• 41383-33-9 1-phenyl-3-piperidino-propan-1-one oxime 
• 952-51-2 1-phenyl-3-(piperidin-1-yl)propan-1-ol 
• 4734-37-6 N-phenyl-3-piperidin-1-yl-propionamide 
• 4380-82-9 N-(2-(piperidin-1-yl)ethyl)benzamide 
• 107517-92-0 2-bromo-1-phenyl-3-piperidino-propan-1-one; hydrobromide 
• 36804-20-3 3,4-diphenyl-1,6-di-piperidin-1-yl-hexane-3,4-diol 
• 94124-54-6 1,1-dimethoxy-1-phenyl-3-(1'-piperidinyl)propan-2-ol 
• 84901-86-0 Z-ω-Piperidinopropiophenon-oxim 
• 123612-80-6 C₂₈H₃₈N₂ 
• 19903-25-4 Z-ω-Piperidinopropiophenon-oxim-hydrochlorid 
• 98013-04-8 1,3,5-tribenzoylcyclohexane 
• 97361-42-7 1-phenyl-3-piperidino-propan-1-one oxime ; hydrochloride 
• 768-03-6 Phenyl vinyl ketone 

Relevant academic research and scientific papers

Investigation of inhibitory properties of some hydrazone compounds on hCA I, hCA II and AChE enzymes

Recently, inhibition of carbonic anhydrase (hCA) and acetylcholinesterase (AChE) have appeared as a promising approach for pharmacological intervention in a variety of disorders such as glaucoma, epilepsy, obesity, cancer, and Alzheimer's disease. Keeping this in mind, N,N′-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides, N1-N11, P1, P4-P8, and R1-R6, were synthesized to investigate their inhibitory activity against hCA I, hCA II, and AChE enzymes. All compounds in N, P, and R-series inhibited hCAs (I and II) and AChE more efficiently than the reference compounds acetazolamide (AZA), and tacrine. According to the activity results, the most effective inhibitory compounds were in R-series with the Ki values of 203 ± 55–473 ± 67 nM and 200 ± 34–419 ± 94 nM on hCA I, and hCA II, respectively. N,N′-Bis[1-(4-fluorophenyl)-3-(morpholine-4-yl)propylidene]hydrazine dihydrochlorides, N8, in N-series, N,N′-Bis[1-(4-hydroxyphenyl)-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides, P4, in P-series, and N,N′-bis[1-(4-chlorophenyl)-3-(pyrrolidine-1-yl)propylidene]hydrazine dihydrochlorides, R5, in R-series were the most powerful compounds against hCA I with the Ki values of 438 ± 65 nM, 344 ± 64 nM, and 203 ± 55 nM, respectively. Similarly, N8, P4, and R5 efficiently inhibited hCA II isoenzyme with the Ki values of 405 ± 60 nM, 327 ± 80 nM, and 200 ± 34 nM, respectively. On the other hand, P-series compounds had notable inhibitory effect against AChE than the reference compound tacrine and the Ki values were between 66 ± 20 nM and 128 ± 36 nM. N,N′-Bis[1-(4-fluorophenyl)-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides, P7, was the most potent compound on AChE with the Ki value of 66 ± 20 nM. The other most promising compounds, N,N′-bis[1-(4-hydroxyphenyl)-3-(morpholine-4-yl)propylidene]hydrazine dihydrochlorides, N4 in N-series and N,N′-bis[1-(4-hydroxyphenyl)-3-(pyrrolidine-1-yl)propylidene]hydrazine dihydrochlorides, R4 in R-series were againts AChE with the Ki values of 119 ± 20 nM, 88 ± 14 nM, respectively.

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.

Dramatically accelerated synthesis of β-aminoketones via aqueous Mannich reaction under combined microwave and ultrasound irradiation

An efficient green chemistry approach to the synthesis of β-aminoketones was developed under combined microwave and ultrasound irradiation. With this technique, the title compounds were rapidly synthesized in aqueous media with good yields. Georg Thieme Verlag Stuttgart.

A modified Mannich reaction using 1,3-dioxolane

Mannich reaction of ketones using 1,3-dioxolane instead of formaldehyde, paraformaldehyde, or 1,3,5-trioxane afforded the corresponding Mannich bases in high yields. Under the same conditions the aminomethylation of aromatics did not proceed but the intramolecular aminomethylation, like a Pictet-Spengler type reaction, proceeded smoothly.

Quinaldinamide derivatives

A novel quinaldinamide derivative having the formula: STR1 wherein each of R1 and R2 independently represents a lower alkyl group or R1 and R2 are combined together with the adjacent nitrogen atom to form a 5-7 membered ring; and X represents the hydrogen atom, a lower alkyl group or a lower alkoxy group, and its acid-addition salt, which show prominent central muscle relaxant effect, namely rigidity relieving effect on anemic decerebrated rigidity.

Novel quinaldinamide derivatives and their preparations

A novel quinaldinamide derivative having the formula: wherein each of R1 and R2 independently represents a lower alkyl group or R1 and R2 are combined together with the adjacent nitrogen atom to form a 5 - 7 membered ring; and X represents the hydrogen atom, a lower alkyl group or a lower alkoxy group,and its acid-addition salt, which show prominent central muscle relaxant effect, namely, rigidity reliev-ing effect on anemic decerebrated rigidity.