80167-56-2

Basic information

• Product Name: methyl 4-(4-methoxyanilino)-4-oxo-2-butenoate
• Synonyms: methyl 4-(4-methoxyanilino)-4-oxo-2-butenoate
• CAS NO: 80167-56-2
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.23592
• Mol File: 80167-56-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 4-(4-methoxyanilino)-4-oxo-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(4-methoxyanilino)-4-oxo-2-butenoate(80167-56-2)
• EPA Substance Registry System: methyl 4-(4-methoxyanilino)-4-oxo-2-butenoate(80167-56-2)

Safety Data

• Hazardous Substances Data: 80167-56-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 37904-20-4 (E)–4-((4-methoxyphenyl)amino)-4-oxobut-2-enoic acid 
• 124156-21-4 ethyl (4-methoxyphenylimino)acetate 
• 78140-66-6 3-chlorocarbonylacrylic acid methyl ester 
• 24870-10-8 N-(4-methoxyphenyl)maleamic acid 
• 80167-51-7 (Z)-3-(4-Methoxy-phenylcarbamoyl)-acrylic acid methyl ester 

Downstream Products

• 106691-38-7 N-(4-Methoxy-phenyl)-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetamide 

Relevant articles and documents

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore

Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.

Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide

A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.

Reactions of Cyclic Anhydrides: Part V - Acid-catalysed Esterification of Maleanilic and Fumaranilic Acids and Evidence of Activation by Carboxamido Function

Maleanilic and fumaranilic acids undergo acid catalysed esterification with methanol under very mild conditions.Intramolecular activation involving carboxamido group appears likely in this reactions.