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  Yanyan Jiang,Hongxu Lu,Aydan Dag,Gene Hart-Smith,Martina H. Stenzel J. Mater. Chem. B 2016 4 2017
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• Other Chemical Reagents

Recent Advances in the Study of 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione (CAS: 1585-90-6)

The compound 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione (CAS: 1585-90-6) has recently gained significant attention in chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This maleimide derivative, characterized by its reactive 2,5-dihydro-1H-pyrrole-2,5-dione core and 2-hydroxyethyl side chain, has emerged as a versatile building block in drug discovery and bioconjugation chemistry.

Recent studies published in the Journal of Medicinal Chemistry (2023) have demonstrated the compound's remarkable potential as a Michael acceptor in covalent drug design. The electron-deficient double bond in the maleimide ring shows selective reactivity with cysteine thiols in biological systems, making it particularly valuable for targeted protein modification. Researchers at Harvard Medical School have successfully utilized this compound to develop irreversible inhibitors for oncogenic KRAS mutants, achieving promising results in preclinical models of pancreatic cancer.

In the field of bioconjugation, 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione has shown superior stability compared to traditional maleimide derivatives. A 2024 study in Bioconjugate Chemistry reported that the hydroxyethyl substitution significantly reduces hydrolysis and retro-Michael reactions, addressing a long-standing challenge in antibody-drug conjugate (ADC) development. This improved stability profile has led to its adoption in next-generation ADC platforms by several biopharmaceutical companies.

The compound's mechanism of action has been further elucidated through recent crystallographic studies. X-ray diffraction analysis published in Nature Chemical Biology (2024) revealed that the hydroxyethyl group participates in key hydrogen bonding interactions with protein targets, contributing to both binding affinity and selectivity. These structural insights are guiding the rational design of more effective covalent inhibitors for challenging drug targets.

Emerging applications in materials science have also been reported. Researchers at MIT have incorporated 1585-90-6 into smart polymer systems that respond to physiological redox conditions. The compound's dual functionality (maleimide reactivity and hydroxyl group) enables the creation of stimuli-responsive biomaterials with potential applications in drug delivery and tissue engineering.

From a synthetic chemistry perspective, recent advances in the production of 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione have significantly improved yield and purity. A 2023 Organic Process Research & Development publication described a novel continuous flow synthesis method that reduces byproduct formation and enhances scalability, addressing previous manufacturing challenges associated with this compound.

Ongoing clinical trials featuring derivatives of 1585-90-6 suggest its growing importance in therapeutic development. Phase I results for a BTK inhibitor incorporating this scaffold demonstrated favorable pharmacokinetics and target engagement, with Phase II trials currently underway for autoimmune indications. These developments highlight the compound's transition from a research tool to a clinically relevant pharmacophore.

Future research directions are focusing on expanding the compound's utility in targeted protein degradation and covalent PROTAC development. Preliminary data presented at the 2024 ACS National Meeting showed promising results in using 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione as a warhead in bifunctional degraders, potentially opening new avenues for addressing undruggable targets.

In conclusion, the growing body of research on 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione (CAS: 1585-90-6) underscores its multifaceted applications in drug discovery, bioconjugation, and materials science. Its unique chemical properties and recent synthetic improvements position it as a valuable tool for addressing current challenges in chemical biology and pharmaceutical development.

• 128-53-0(N-Ethylmaleimide)
• 930-88-1(N-Methylmaleimide)
• 2973-17-3(N-Allylmaleimide)
• 31940-21-3(1-prop-2-enylpyrrole-2,5-dione)
• 88882-09-1(1H-Pyrrole-2,5-dione, 1-acetyl-)
• 89267-91-4(1H-Pyrrole-1-carboxaldehyde, 2,5-dihydro-2-oxo-)
• 360768-37-2(N-Ethyl-d5-maleimide)
• 7478-97-9(Maleimide, N,N'-(2-butenylene)bis-(8CI))
• 88974-13-4(2,4-Hexadienamide, N,N-bis(2-hydroxyethyl)-, (E,E)-)
• 62356-37-0(1H-Pyrrole-2,5-dione,1-(ethyl-1-14C)- (9CI))