Cas no 116610-44-7 (2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)-)
2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- Chemical and Physical Properties
Names and Identifiers
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- 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)-
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- Inchi: 1S/C11H10BrNO2/c1-7-2-4-8(5-3-7)13-10(14)6-9(12)11(13)15/h2-5,9H,6H2,1H3
- InChI Key: USRLTHTVODZQPS-UHFFFAOYSA-N
- SMILES: N1(C2=CC=C(C)C=C2)C(=O)CC(Br)C1=O
Experimental Properties
- Density: 1.599±0.06 g/cm3(Predicted)
- Melting Point: 163 °C
- Boiling Point: 467.4±45.0 °C(Predicted)
- pka: -1.90±0.40(Predicted)
2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Enamine | EN300-267023-1.0g |
3-bromo-1-(4-methylphenyl)pyrrolidine-2,5-dione |
116610-44-7 | 1.0g |
$0.0 | 2023-03-01 |
2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- Related Literature
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Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
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Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
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Daniel Messmer,Stefan Salentinig,Jakob Heier Nanoscale, 2019,11, 6929-6938
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Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
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Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
Additional information on 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)-
Research Brief on 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- (CAS: 116610-44-7): Recent Advances and Applications
2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- (CAS: 116610-44-7) is a brominated pyrrolidinedione derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug discovery. This compound, characterized by its unique structural features, has been explored as a key intermediate in the synthesis of various bioactive molecules. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in the areas of anti-inflammatory, anticancer, and antimicrobial research.
A 2023 study published in the Journal of Medicinal Chemistry investigated the compound's utility as a building block for the synthesis of small-molecule inhibitors targeting protein-protein interactions (PPIs). The researchers demonstrated that the bromine moiety at the 3-position of the pyrrolidinedione ring enhances the compound's reactivity, enabling efficient functionalization for further derivatization. The study also reported that the 4-methylphenyl group contributes to improved lipophilicity, which is advantageous for membrane permeability in drug candidates.
In the context of anticancer research, a team from the University of Cambridge recently utilized 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- as a precursor for the development of novel HDAC (histone deacetylase) inhibitors. Their findings, published in Bioorganic & Medicinal Chemistry Letters, revealed that derivatives of this compound exhibited potent inhibitory activity against HDAC6, a target implicated in various cancers. The study emphasized the compound's versatility in structure-activity relationship (SAR) studies, owing to its modifiable functional groups.
Another significant advancement was reported in a 2024 European Journal of Medicinal Chemistry article, where researchers explored the antimicrobial properties of 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- derivatives. The study identified several analogs with broad-spectrum activity against drug-resistant bacterial strains, including MRSA. The presence of the bromine atom was found to be critical for the observed bioactivity, likely due to its role in enhancing electrophilic reactivity and facilitating interactions with bacterial enzymes.
From a synthetic chemistry perspective, recent work has focused on optimizing the preparation of 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)-. A 2023 Organic Process Research & Development paper described a scalable, high-yield synthesis route that employs green chemistry principles, minimizing the use of hazardous reagents. This development is particularly important for potential industrial-scale production of the compound and its derivatives.
Looking forward, the unique structural features of 2,5-Pyrrolidinedione, 3-bromo-1-(4-methylphenyl)- continue to make it a valuable scaffold in drug discovery. Current research directions include its application in PROTAC (proteolysis targeting chimera) design and as a warhead in covalent inhibitor development. The compound's CAS number (116610-44-7) has become increasingly prevalent in patent applications, indicating growing commercial interest in its pharmaceutical applications.
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