288073-90-5

Basic information

• Product Name: 3,5-bis(4-methoxybenzylidene)-1-methyl-4-piperidinone
• Synonyms: 3,5-bis(4-methoxybenzylidene)-1-methyl-4-piperidinone
• CAS NO: 288073-90-5
• Molecular Formula: C22H23NO3
• Molecular Weight: 349.42292
• Mol File: 288073-90-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-bis(4-methoxybenzylidene)-1-methyl-4-piperidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-bis(4-methoxybenzylidene)-1-methyl-4-piperidinone(288073-90-5)
• EPA Substance Registry System: 3,5-bis(4-methoxybenzylidene)-1-methyl-4-piperidinone(288073-90-5)

Safety Data

• Hazardous Substances Data: 288073-90-5(Hazardous Substances Data)

Upstream product

• 1445-73-4 1-Methyl-4-piperidone 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1289514-36-8 (4R,8E)-2-amino-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-8-(4-methoxyphenylmethylene)-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile 
• 1446347-71-2 (4S,8E)-2-amino-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-8-(4-methoxyphenylmethylene)-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile 
• 1623098-50-9 (E)-8-(4-methoxybenzylidene)-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-6-methyl-2-phenylpyrido[4,3-d]pyrimidine 

Relevant articles and documents

Synthesis and biological evaluation of certain α,β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents

A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3

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A series of heterocyclic α,β-unsaturated carbonyl compounds (1a-1d, 2a-2d, 3a-3d, 4a-3d, and 5a-5d) with 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore were synthesized for the development of anticancer and multidrug resistance reverting agents. The antiproliferative activities were tested against nine human cancer cell lines. Approximately 73% of the IC50 values were below 5 μm, while 35% of these figures were submicromolar, and compounds 3a-3d with 4-trifluoro methyl in the arylidene benzene rings were the most potent, since their IC50 values are between 0.06 and 3.09 μm against all cancer cell lines employed. Meanwhile, their multidrug resistance reversal properties and cellular uptake were further examined. The data displayed that all of these compounds could reverse multidrug resistance, particularly, compounds 3a and 4a demonstrated both potent multidrug resistance reverting properties and strong antiproliferative activities, which can be taken as leading molecules for further research of dual effect agents in tumor chemotherapy.

Ene synthesis of bicyclic arylmethylenedihydropyrazoles using 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione

8-Acetyl-7-aryl-2-arylmethylene-8,9-diaza- and 4,8,9-triazabicyclo[4.3.0]non-9-enes react with 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione, following the ene addition pattern. Under similar conditons 7-aryl-2-arylmethylene-8-methyl-8,9-diazabicyclo[4.3.0]non-9-enes give rise to both mono- and polyaddition products. The product structures were studied by 1H and 13C NMR, IR, and UV spectroscopy and single crystal X-ray diffraction.

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Indole-based compounds 30-63 were synthesized by the multi-component 1,3-dipolar cycloaddition reaction of 1-alkyl-3,5-bis(arylidene)-4-piperidones 11-25 with azomethine ylides (generated by the condensation of isatins 26-28 with sarcosine 29). The single crystal X-ray studies of 46 and 48 supported the regio- and stereoselectivity of the reaction. Most of the synthesized spiro-indoles exhibited potent antitumor properties against the HeLa (cervical cancer) cell line through in vitro sulfo-rhodamine-B bioassay, higher than that of cisplatin. Only compound 54 showed bio-potency against the HepG2 (hepatocellular cancer) cell line, comparable to that of doxorubicin hydrochloride (standard reference). 3D-Pharmacophore and 2D-QSAR studies were used to validate the observed biological data and determine the most important parameters controlling activity. The estimated bio-properties from the computational studies showed high approximations to the experimental data.

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