241495-46-5

Basic information

• Product Name: 1-(4-methylbenzyl)piperidin-4-one
• Synonyms: 1-(4-methylbenzyl)piperidin-4-one;1-[(4-methylphenyl)methyl]-4-piperidinone;1-[(4-methylphenyl)methyl]piperidin-4-one
• CAS NO: 241495-46-5
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.28018
• Mol File: 241495-46-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 325.3±27.0 °C(Predicted)
• Appearance: /
• Density: 1.077±0.06 g/cm3(Predicted)
• PKA: 7.23±0.20(Predicted)
• CAS DataBase Reference: 1-(4-methylbenzyl)piperidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methylbenzyl)piperidin-4-one(241495-46-5)
• EPA Substance Registry System: 1-(4-methylbenzyl)piperidin-4-one(241495-46-5)

Safety Data

• Hazardous Substances Data: 241495-46-5(Hazardous Substances Data)

Usage

General Description

1-(4-methylbenzyl)piperidin-4-one, also known as 4-Methylbenzylpiperidin-4-one, is a chemical compound with the molecular formula C14H19NO. It is a piperidone derivative that is commonly used in research and pharmaceutical applications. 1-(4-methylbenzyl)piperidin-4-one has been documented for its potential as a central nervous system stimulant and analgesic agent. It is also known for its use in the synthesis of various pharmaceutical drugs and as a precursor in organic chemistry. Additionally, 1-(4-methylbenzyl)piperidin-4-one has a range of other potential chemical and biological activities, making it a compound of interest in various fields of study.

Upstream product

• 41979-39-9 4-piperidone hydrochloride 
• 104-81-4 4-Methylbenzyl bromide 
• 292638-85-8 acrylic acid methyl ester 
• 104-84-7 para-methylbenzylamine 
• 1226272-59-8 C₁₅H₁₉NO₃ 
• 104-82-5 4-Methylbenzyl chloride 
• 177-11-7 4,4-ethylenedioxy-piperidine 
• 904750-06-7 8-(4-methyl-benzyl)-1,4-dioxa-8-aza-spiro[4.5]decane 

Downstream Products

• 562824-87-7 N-[1-(4-methyl-benzyl)-piperidin-4-ylidene]-N'-(2-nitro-phenyl)-hydrazine 
• 1266543-23-0 N-(4-methylbenzyl)-3,5-bis(4-methylbenzylidene)-4-piperidone 
• 1266543-19-4 N-(4-methylbenzyl)-3,5-bis(benzylidene)-4-piperidone 
• 1266543-24-1 N-(4-methylbenzyl)-3,5-bis(4-methoxybenzylidene)-4-piperidone 
• 1369499-56-8 8-(4-isopropylbenzylidene)-4-(4-isopropylphenyl)-6-(4-methylbenzyl)-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]hydropyrimidine-2-thione 
• 1369499-58-0 4-(4-fluorophenyl)-6-(4-methylbenzyl)-8-(4-fluorobenzylidene)-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]hydropyrimidine-2-thione 
• 1352565-06-0 5-(4-methylbenzyl)-7-(4-methylbenzylidene)-3,3a,4,5,6,7-hexahydro-3-(4-methylphenyl)-2-phenyl-2H-pyrazolo[4,3-c]pyridine 
• 1352565-09-3 5-(4-methylbenzyl)-7-(4-methoxylbenzylidene)-3,3a,4,5,6,7-hexahydro-3-(4-methoxylphenyl)-2-phenyl-2H-pyrazolo[4,3-c]pyridine 
• 1352565-12-8 7-(4-fluorobenzylidene)-5-(4-methylbenzyl)-3,3a,4,5,6,7-hexahydro-3-(4-fluorophenyl)-2-phenyl-2H-pyrazolo[4,3-c]pyridine 
• 1350909-69-1 C₂₇H₂₃F₂NO 
• 1266543-27-4 C₂₇H₂₃Cl₂NO 

Relevant articles and documents

HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor

HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the putatively mutagenic aromatic-amine building block that resulted in a novel, aminomethylindole compound family. The most balanced physico-chemical and pharmacological profile was found in case of compound 55. Docking study revealed an intersubunit binding site to be the most probable for our compounds. 55 demonstrated favorable cognitive enhancing profile not only in scopolamine-induced amnesia (place recognition test in mice) but also in natural forgetting (novel object recognition test in rats). Compound 55 was, furthermore, active in a cognitive paradigm of high translational value, namely in the rat touch screen visual discrimination test. Therefore, 55 was selected as a lead compound for further optimization. Based on the obtained favorable results, the invented aminomethylindole cluster may provide a viable approach for cognitive enhancement through positive allosteric modulation of α7 nAChRs.

Novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives: Synthesis, crystal structure, fluorescence properties and cytotoxicity evaluation against human breast cancer cells

A series of novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives (II) have been designed and synthesized. The target compounds have been identified by elemental analysis and spectral (1H NMR, IR, and MS) data and the absolute configuration of compound (II 1 ) was confirmed by single crystal X-ray diffraction. The cytotoxicity of the target compounds have been evaluated in vitro against two human breast cancer cell lines MCF-7 and MDA-MB-231 by MTT assay. Most compounds exhibited good inhibition, and compounds II 21 (IC50 = 4.7 μM for MCF-7 and IC50 = 9.3 μM for MDA-MB-231), II 33 (IC50 = 2.4 μM for MCF-7 and IC50 = 4.2 μM for MDA-MB-231) and II 40 (IC50 = 3.3 μM for MCF-7 and IC50 =8.6 μM for MDA-MB-231) displayed better inhibitory activity than 5-fluorouracil (IC 50 = 4.8 μM for MCF-7 and IC50 = 9.6 μM for MDA-MB-231, respectively). Flow cytometric analysis and DNA fragmentation suggest that II 33 is cytotoxic and able to induce the apoptosis of MCF-7 cells. The fluorescence properties of compounds II 1, II 6, II 11, II 16, II 23, II 28, and II 35 were also studied and compound II 28 afforded the highest photoluminescence quantum yield (38%).

Synthesis, crystal structure and anticancer activities of tetrahydropyrido[4,3-d]dihydropyrimidine-2-thiones

A new series of tetrahydropyrido[4,3-d]dihydropyrimidine-2-thiones (3a-3x) were designed and synthesized. Their structures were confirmed by1H NMR, IR, MS and elemental analysis, and the conformation of compound 3j was confirmed by X-ray diffraction. Preliminary bioassays indicated that most of the target compounds presented good antiproliferative activities against leukemic K562 cells, ovarian cancer HO-8910 cells and liver cancer SMMC-7721 cells in vitro. Among them the compounds 3i and 3m afford the best activity, the IC 50 of them were 3.22 and 3.65 iμg/mL against leukemic K562 cells, respectively, which were lower than the anticancer drug of clinical practice 5-FU (IC50=8.56 iμg/mL). Preliminary mechanism of action studies revealed that compound 3i caused DNA fragmentation and activated caspase-3/7 in leukemic K562 cells. A new series of tetrahydropyrido[4,3-d] dihydropyrimidine-2-thiones (3a-3x) were synthesized and the conformation of compound 3j was confirmed by X-ray diffraction. Preliminary bioassays indicated that most of the target compounds presented good antiproliferative activities against leukemic K562 cells, ovarian cancer HO-8910 cells and liver cancer SMMC-7721 cells in vitro. Preliminary mechanism of action studies revealed that compound 3i caused DNA fragmentation and activated caspase-3/7 in leukemic K562 cells. Copyright