67200-34-4

Basic information

• Product Name: SMER 3
• Synonyms: SMER 3;9H-Indeno[1,2-e][1,2,5]oxadiazolo[3,4-b]pyrazin-9-one;9H-indeno[2,1-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one;OC1181, 9H-indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one
• CAS NO: 67200-34-4
• Molecular Formula: C11H4N4O2
• Molecular Weight: 224.17506
• Mol File: 67200-34-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 283-284 °C(Solv: ethanol (64-17-5))
• Boiling Point: 437.2 °C at 760 mmHg
• Flash Point: 218.2 °C
• Appearance: yellow/
• Density: 1.665 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥30mg/mL
• PKA: -8.15±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
• CAS DataBase Reference: SMER 3(CAS DataBase Reference)
• NIST Chemistry Reference: SMER 3(67200-34-4)
• EPA Substance Registry System: SMER 3(67200-34-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 1
• Hazardous Substances Data: 67200-34-4(Hazardous Substances Data)

Usage

Description

SMER3 is a selective inhibitor of Skp1-Cullin-F-box (SCF)MET30 ubiquitin ligase, an E3 ligase that regulates transcription, cell-cycle control, and immune response. It is a small molecule enhancer of rapamycin, enhancing yeast cell lethality in response to rapamycin. SMER3, at 5 μM, upregulates a set of methionine biosynthesis genes by altering the SCFMET30 complex, preventing ubiquitination of target proteins, including Met4. As ubiquitin E3 ligases are involved in tumorigenesis, SMER3 has potential applications in cancer research.

Uses

Used in Biological Studies:
SMER 3 is used as a pharmacological tool for evaluating the role of mTOR (mammalian target of rapamycin) in growth control in eukaryotic cells, as it acts as an inhibitor.
Used in Cancer Research:
SMER 3 is used as a potential therapeutic agent for cancer, as it prevents ubiquitination of target proteins and has the potential to disrupt tumorigenesis processes.
Used in Drug Development:
SMER 3 is used as a lead compound in the development of new drugs targeting the SCFMET30 ubiquitin ligase, which could have implications for various diseases, including cancer.

References

1) Aghajanyy et al. (2010), Chemical genetics of TOR identifies an SCF family E3 ubiquitin ligase inhibitor; Nat. Biotechnol., 28 738

Upstream product

• 938-24-9 indantrione 
• 17220-38-1 3,4-diaminofurazan 
• 83-33-0 inden-1-one 
• 485-47-2 indan-1,2,3-trione hydrate 

Relevant articles and documents

Reaction of diaminofurazane with ninhydrin

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METHODS AND COMPOSITIONS OF SUBSTITUTED 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE ANALOGS AS INHIBITORS OF BETA-CATENIN/T-CELL FACTOR PROTEIN-PROTEIN INTERACTIONS

In one aspect, the invention relates to substituted 5H-[1,2,5]oxadiazolo [3',4':5,6]pyrazino[2,3-b]indole analogues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g., various tumors and cancers, associated with a β-catenin/T-cell factor interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Ionic liquids - Advanced reaction media for organic synthesis

The advantages in the application of ionic liquids as reaction media in organic synthesis, i.e., in the preparation of chromane derivatives, substituted pyrazines, 4-aminofuran-2(5H)-ones, or in bromination of Levulinic acid or dehydration of alcohols, saccharides, and polysaccharides, have been demonstrated on several examples. Ionic liquids with Bronsted acidity have been shown to possess catalytic activity and provide access to convenient technologies for the preparation of various useful compounds. Copyright Merck KGaA.