6954-65-0

Usage

Uses

Used in Organic Synthesis:
N-(2,4-DIFLUOROPHENYL)MALEIMIDE is used as a dienophile in Diels-Alder reactions for the formation of complex organic molecules, contributing to the advancement of organic chemistry.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-(2,4-DIFLUOROPHENYL)MALEIMIDE is employed as a building block in the synthesis of new drugs, facilitating the creation of innovative therapeutic agents.
Used in Agrochemical Development:
Similarly, in agrochemical research, N-(2,4-DIFLUOROPHENYL)MALEIMIDE is utilized to develop new pesticides and other agricultural chemicals, enhancing crop protection and yield.
Used in Material Science:
N-(2,4-DIFLUOROPHENYL)MALEIMIDE is used in material science for its potential to form covalent bonds with other molecules, leading to the development of new materials with unique properties.
Used in Polymer Chemistry:
In the field of polymer chemistry, N-(2,4-DIFLUOROPHENYL)MALEIMIDE is applied to create novel polymers with specific characteristics, broadening the scope of polymer applications.

InChI:InChI=1/C10H5F2NO2/c11-6-1-2-8(7(12)5-6)13-9(14)3-4-10(13)15/h1-5H

Upstream product

• 367-25-9 2,4-difluorophenylamine 
• 6954-64-9 N-(2,4-Difluorphenyl)-maleamsaeure 

Downstream Products

• 1027211-12-6 C₂₇H₃₃F₂NO₆Si 
• 1312543-98-8 C₂₅H₂₃F₂NO₂ 

Relevant academic research and scientific papers

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.