219851-87-3

Basic information

• Product Name: Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate
• Synonyms: Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate
• CAS NO: 219851-87-3
• Molecular Formula: C₁₆H₂₁NO₆S
• Molecular Weight: 355.40604
• Mol File: 219851-87-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate(219851-87-3)
• EPA Substance Registry System: Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate(219851-87-3)

Safety Data

• Hazardous Substances Data: 219851-87-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-(N-(tert-butoxycarbonyl)-4-MethylphenylsulfonaMido)acrylate is a chemical compound with the molecular formula C16H19NO6S. It is a sulfonamide derivative of acrylate and is commonly used in the synthesis of various organic compounds. The tert-butoxycarbonyl (Boc) group attached to the nitrogen atom serves as a protecting group, allowing for selective reactions to occur at other functional groups in the molecule. The presence of the acrylate moiety makes it a versatile building block for the synthesis of polymers, pharmaceuticals, and other functional materials. Additionally, the compound’s sulfonamide group gives it biological activity, making it potentially useful in medicinal chemistry applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 17136-46-8 methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 253786-63-9 N-tosyl DL-serine methyl ester 

Downstream Products

• 475598-30-2 Boc-(E)-ΔAla[β-(4-bromophenylsulfanyl)]-OMe 
• 773896-53-0 N,N-bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine 
• 475598-25-5 (E)-Boc-ΔSer(p-tolylsulfinyl)-OMe 

Relevant articles and documents

New anticancer agents mimicking protein recognition motifs

The novel tetrasubstituted pyrrole derivatives 8g, 8h, and 8i showed selective cytotoxicity against M14 melanoma cells at low micromolar concentration. Structure-activity relationships (SARs) indicated the presence of three aromatic substituents on the pyrrole core as necessary for biological activity. Computational studies strongly suggest that the peculiar 3D orientation of these substituents is able to reproduce the hydrophobic side chains in LxxLL-like protein recognition motifs. Biological results showed altered p53 expression and nuclear translocation in cells sensitive to the compounds, suggesting p53 involvement in their anticancer mechanism of action. Unfortunately, because of poor solubility of the active analogues, it was not possible to perform further investigation by NMR techniques. Pharmacophore models were generated and used to perform 3D searches in molecular databases. Results indicated that two compounds share the same pharmacological profile and the same pharmacophoric features with our new derivatives, and one of them inhibited MDM2-MDM4 heterodimer formation.

Efficient synthesis of dehydroamino acid derivatives

By using a DMAP catalysed reaction of β-hydroxyamino acid derivatives with tert-butylpyrocarbonate, the corresponding dehydroamino acid derivatives were obtained in high yields.