919091-63-7

Basic information

• Product Name: 4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-, (3E,3E)-
• Synonyms: 3,5-Bis-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-piperidin-4-one;(3E,5E)-3,5-bis(4-nitrobenzylidene)piperidin-4-one;3,5-bis(4-nitrobenzylidene)-4-piperidinone;3,5-bis(4-nitrophenylmethylene)-4-piperidone;(3E,5E)-3,5-bis[(4-nitrophenyl)methylene]-4-piperidone
• CAS NO: 919091-63-7
• Molecular Formula: C19H15N3O5
• Molecular Weight: 365.345
• Mol File: 919091-63-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 230-233 °C(Solv: ethyl ether (60-29-7); acetonitrile (75-05-8))
• Boiling Point: 588.5±50.0 °C(Predicted)
• Density: 1.414±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-, (3E,3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-, (3E,3E)-(919091-63-7)
• EPA Substance Registry System: 4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-, (3E,3E)-(919091-63-7)

Safety Data

• Hazardous Substances Data: 919091-63-7(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 41979-39-9 4-piperidone hydrochloride 
• 41661-47-6 piperidin-4-one 

Downstream Products

• 330450-45-8 (3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-(prop-2-enoyl)piperidin-4-one 

Relevant articles and documents

Design, synthesis and tumour-selective toxicity of novel 1-[3-{3,5-bis(Benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes and related quaternary ammonium salts

A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a–h and related quaternary ammonium salts 4a–h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells

Synthesis, characterization, and optimization for in vivo delivery of a nonselective isopeptidase inhibitor as new antineoplastic agent

Bis-arylidenecycloalkanones structurally related to the nonselective isopeptidase inhibitor G5 were synthesized and tested for cytotoxic activity against glioblastoma cells. Cytotoxicities correlate well with Hammett σ constants for substituted arylidene groups, confirming the proposed inhibition mechanism. A new inhibitor (2c) based on the 4-hydroxycyclohexanone scaffold, which favors apoptosis over necrosis, was selected for further development. 2c inhibited representative deubiquitinases with micromolar IC50, and its proapoptotic activity was studied on several cancer cell lines. Inhibitor 2c was conjugated to PEG via dicarbamate and diester linkers. While the dicarbamate was inactive, the diester (2cPE) behaves like a prodrug and is converted into the active species 2c by secreted esterase activities. Finally, 2cPE was also tested in vivo on A549 lung carcinoma xenografts generated in mice. Intravenous treatment with 2cPE led to a significant reduction in primary tumor growth, without appreciable toxicity to mice.

ANTINEOPLASTIC COMPOUNDS

The present invention relates to 4-piperidone derivatives represented by the following formula (I) and the acid addition salts thereof. The method of preparation and antineoplastic activity of the said compounds are disclosed. A number of the compounds po