SMER 3

Base Information

• Chemical Name: SMER 3
• CAS No.: 67200-34-4
• Molecular Formula: C11H4N4O2
• Molecular Weight: 224.1751
• Mol file: 67200-34-4.mol

Synonyms:Indeno[1, 2-b]furazano[3, 4-E]pyrazin-9-one;

Chemical Property of SMER 3

Chemical Property:

• Melting Point: 283-284 °C(Solv: ethanol (64-17-5))
• Boiling Point: 437.2 °C at 760 mmHg
• PKA: -8.15±0.20(Predicted)
• Flash Point: 218.2 °C
• PSA: 81.77000
• Density: 1.665 g/cm³
• LogP: 1.22420
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥30mg/mL

Purity/Quality:

99%+, ^*data from raw suppliers

SMER 3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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 , in that it enhances 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: SMER3 is used in biological studies to evaluate the pharmacological activity as it is discovered as an inhibitor. SMER3 inhibits mTOR (mammalian target of rapamycin) which plays a key role in the growth control in eukaryotic cells. SMER is the small-molecule enhancer of rapamycin.

Technology Process of SMER 3

There total 5 articles about SMER 3 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

indantrione (938-24-9) + 3,4-diaminofurazan (17220-38-1) → 9H-indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one (67200-34-4)

Guidance literature:

With acetic acid; In ethanol; for 8h; Heating;

DOI:10.1002/jccs.202100438

Reference yield: 72.0%

indan-1,2,3-trione hydrate (485-47-2) + 3,4-diaminofurazan (17220-38-1) → 9H-indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one (67200-34-4)

Guidance literature:

With acetic acid; In ethanol; at 20 ℃; for 24h; Reflux;

DOI:10.1021/acs.jmedchem.5b00223

Reference yield:

inden-1-one (83-33-0) → 9H-indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one (67200-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide / 1,4-dioxane / 90 °C

2: acetic acid / ethanol / 8 h / Heating

With selenium(IV) oxide; acetic acid; In 1,4-dioxane; ethanol;

DOI:10.1002/jccs.202100438

upstream raw materials:

indan-1,2,3-trione hydrate

3,4-diaminofurazan

indantrione

inden-1-one

Refernces

• 1、 Chen, Wei-Chia,Chen, Chia-Ling,Chang, Tzu-Ting,Hsieh, Feng-Chun,Chen, Wei-Sheng,Li, Wen-Shan. "Design, synthesis, and characterization of oxadiazolopyrazine analogs with application as anticancer agents". . p. 375 - 387. Retrieved 2021/12/23.
• 2、 Catrow, J. Leon,Zhang, Yongqiang,Zhang, Min,Ji, Haitao. "Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein-Protein Interaction through the Optimization of the Acyl Hydrazone Moiety". . p. 4678 - 4692. Retrieved 2015/06/25.