314245-33-5

Basic information

• Product Name: 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone
• Synonyms: 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone;IU1;1-(1-(4-fluorophenyl)-2,5-diMethyl-1H-pyrrol-3-yl)-2-(pyrrolidin-1-yl)ethanone;Ethanone, 1-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)-
• CAS NO: 314245-33-5
• Molecular Formula: C18H21FN2O
• Molecular Weight: 300
• Product Categories: Inhibitor;Inhibitors
• Mol File: 314245-33-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 437.034 °C at 760 mmHg
• Flash Point: 218.111 °C
• Appearance: off-white to light brown/
• Density: 1.169 g/cm³
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >10mg/mL
• PKA: 8.20±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone(314245-33-5)
• EPA Substance Registry System: 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone(314245-33-5)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 314245-33-5(Hazardous Substances Data)

Usage

Description

1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is a complex organic compound characterized by its unique molecular structure. It is a derivative of pyrrole, a heterocyclic compound with a five-membered ring containing two hydrogen atoms and three nitrogen atoms. The presence of fluorophenyl and pyrrolidinyl groups in its structure contributes to its potential applications in various fields.

Uses

1. Used in Pharmaceutical Applications:
1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is used as a selective inhibitor for [application type] in [application reason]. It has been found to inhibit Ubiquitin Specific Peptidase 14 (USP14) in human neuroblastoma cells (SH-SY5Y) and in ubiquitin-rhodamine hydrolysis plate assays, with an IC50 value of less than 4 μM.
2. Used in Antiviral Applications:
In the field of antiviral research, 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is used as an inhibitor for [application type] to inhibit Dengue virus replication [application reason]. Its ability to interfere with the viral life cycle makes it a potential candidate for the development of antiviral therapies.
3. Used in Prion Disease Research:
1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is used as an activator for [application type] in prion-infected CAD5 cells [application reason]. Activation of the ubiquitin proteasome system by this compound is sufficient to induce clearance of polyubiquitinated substrates and reduce the load of misfolded prion proteins, offering a potential therapeutic approach for prion diseases.
4. Used in Neuroprotection:
In the neuroscience field, 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is used as a neuroprotective agent for [application type] to attenuate ischemia/reperfusion-induced neuronal injury in a mouse model [application reason]. Its cell permeable nature allows it to cross the blood-brain barrier, making it a promising candidate for the treatment of neurodegenerative disorders.
5. Used in Chemical Synthesis:
1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone is also used as a synthetic intermediate for [application type] in the synthesis of various pharmaceuticals and chemical compounds [application reason]. Its unique structure and functional groups make it a versatile building block for the development of new molecules with potential applications in various industries.

Biochem/physiol Actions

IU1 is an inhibitor of USP14, a deubiquitinating enzyme associated with the proteasome. The proteasome mediates the cellular degradation of oxidized, damaged and misfolded proteins which, if not removed, accumulate and become toxic to cells. Proteins targeted for proteasomal degradation are first ubiquitinated, with longer length ubiquitin chains interacting more strongly with the proteasome. Deubiquitinating enzymes (DUBs) such as USP14 interfere with the degradation process. IU1 inhibits USP14-mediated ubiquitin "chain-trimming" thereby enhancing substrate degradation by the proteasome. The compound may help to eliminate toxic proteins more effectively by enhancing their degradation.

References

1) Lee et al. (2010), Enhancement of proteasome activity by a small-molecule inhibitor of USP14; Nature, 467 1179 2) Lee et al. (2010), Trimming of ubiquitin chains by proteasome-associated deubiquitinating enzymes; Mol. Cell. Proteomics, 10 R110 3) Nag and Finley (2012), A small-molecule inhibitor of deubiquitinating enzyme USP14 inhibits Dengue virus replication; Virus Res., 165 103 4) McKinnon et al. (2016), Prion-mediated neurodegeneration is associated with early impairment of the ubiquitin-proteasome system; Acta Neuropathol., 131 411 5) Min et al. (2017), USP14 inhibitor attenuates cerebral ischemia/reperfusion-induced neuronal injury in mice; J. Neurochem., 140 826 6) Homma et al. (2015); Ubiquitin-specific protease 14 modulates degradation of cellular prion protein; Sci. Rep. 5 11028 ?[FOCUS CITATION]