6943-90-4

Basic information

• Product Name: 1-phenethylpyrrole-2,5-dione
• Synonyms: 1-Phenethyl-3-pyrroline-2,5-dione;1-(2-phenylethyl)-3-pyrroline-2,5-quinone;1-(2-phenylethyl)pyrrole-2,5-dione;1H-Pyrrole-2,5-dione, 1-(2-phenylethyl)-;Maleimide, N-phenethyl-;Maleimide-Related Compound 6;N-(2-Phenylethyl)maleimide
• CAS NO: 6943-90-4
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.23
• Mol File: 6943-90-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 354.3°C at 760 mmHg
• Flash Point: 162.8°C
• Appearance: /
• Density: 1.224g/cm³
• Vapor Pressure: 3.37E-05mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 1-phenethylpyrrole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenethylpyrrole-2,5-dione(6943-90-4)
• EPA Substance Registry System: 1-phenethylpyrrole-2,5-dione(6943-90-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6943-90-4(Hazardous Substances Data)

Usage

General Description

1-phenethylpyrrole-2,5-dione, also known as phenethylmaleimide, is a chemical compound that belongs to the class of pyrrole derivatives. It is a yellow crystalline solid that has applications in various fields, including pharmaceuticals, materials science, and organic synthesis. 1-phenethylpyrrole-2,5-dione has been studied for its potential use as a building block in organic synthesis and as a precursor for the development of new pharmaceuticals. It has also been investigated for its potential use in the development of new materials with unique properties. Additionally, 1-phenethylpyrrole-2,5-dione has been studied for its potential therapeutic applications, including anti-tumor and anti-inflammatory properties, making it an interesting compound for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C12H11NO2/c14-11-6-7-12(15)13(11)9-8-10-4-2-1-3-5-10/h1-7H,8-9H2

Upstream product

• 617-48-1 malic acid 
• 64-04-0 phenethylamine 
• 541-59-3 maleiimide 
• 60-12-8 2-phenylethanol 
• 4796-01-4 N-2-phenylethylmaleamic acid 
• 108-31-6 maleic anhydride 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 89143-21-5 1'-Phenethyl-[1,3']bipyrrolidinyl-2',5'-dione 
• 89143-33-9 1-Phenethyl-3-piperidin-1-yl-pyrrolidine-2,5-dione 
• 106058-58-6 1-Phenethyl-3-(4-phenylsulfanyl-phenylamino)-pyrrolidine-2,5-dione 
• 106058-36-0 3-(4-Methoxy-phenylamino)-1-phenethyl-pyrrolidine-2,5-dione 
• 106058-46-2 3-(4-Ethoxy-phenylamino)-1-phenethyl-pyrrolidine-2,5-dione 
• 1016-50-8 N-phenethylsuccinimide 

Relevant articles and documents

Application of maleimide compound as chitin synthase inhibitor

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

Synthesis and anti-HIV-1 activity evaluation for novel 3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives

The search for new molecular constructs that resemble the critical two-metal binding pharmacophore and the halo-substituted phenyl functionality required for HIV-1 integrase (IN) inhibition represents a vibrant area of research within drug discovery. As reported herein, we have modified our recently disclosed 1-[2-(4-fluorophenyl)ethyl]-pyrrole-2,5-dione scaffolds to design 35 novel compounds with improved biological activities against HIV-1. These new compounds show single-digit micromolar antiviral potencies against HIV-1 and low toxicity. Among of them, compound 9g and 15i had potent anti-HIV-1 activities (EC50 50 /EC50 > 100). These two compounds have potential as lead compounds for further optimization into clinical anti-HIV-1 agents.

Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds

The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.