79689-18-2

Usage

Chemical class

Pyrrole-2,5-dione derivatives

Structure

Consists of a pyrrole ring with a dimethylamino propyl group attached at the 3-position

Applications

Organic synthesis and pharmaceutical research

Potential therapeutic properties

Yes

Utilization

Development of various drugs and biologically active molecules

Unique structure

Valuable building block for the synthesis of more complex organic compounds

Upstream product

• 17674-02-1 N-(3-dimethylamino-propyl)-maleamic acid 
• 109-55-7 1-amino-3-(dimethylamino)propane 

Relevant academic research and scientific papers

Synthesis, characterization, and antimicrobial properties of peptides mimicking copolymers of maleic anhydride and 4-methyl-1-pentene

Synthetic amphiphilic copolymers with strong antimicrobial properties mimicking natural antimicrobial peptides were obtained via synthesis of an alternating copolymer of maleic anhydride and 4-methyl-1-pentene. The obtained copolymer was modified by grafting with 3-(dimethylamino)-1-propylamine (DMAPA) and imidized in a one-pot synthesis. The obtained copolymer was modified further to yield polycationic copolymers by means of quaternization with methyl iodide and dodecyl iodide, as well as by being sequentially quaternized with both of them. The antimicrobial properties of obtained copolymers were tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, and Staphylococcus aureus. Both tested quaternized copolymers were more active against the Gram-negative E. coli than against the Gram-positive S. aureus. The copolymer modified with both iodides was best when tested against E. coli and, comparing all three copolymers, also exhibited the best effect against S. aureus. Moreover, it shows (limited) selectivity to differentiate between mammalian cells and bacterial cell walls. Comparing the minimum inhibitory concentration (MIC) of Nisin against the Gram-positive bacteria on the molar basis instead on the weight basis, the difference between the effect of Nisin and the copolymer is significantly lower.

Efficient method for the synthesis of functionalized basic maleimides

A three-step procedure involving Diels-Alder condensation of maleic anhydride with furane, formation of N-substituted imide upon reaction with appropriate diamine, and a final retro Diels-Alder regeneration of the maleic carbon-carbon double bond is proposed for an unequivocal synthesis of N-substituted basic maleimides. The novel method is characterized by mild reaction conditions, easy work-up, high yields, and no need for additional catalysis.