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

Names

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

[Synonym ]:
Indeno[1,2-b]furazano[3,4-E]pyrazin-9-one,
5-Oxoindeno<1,2-e>furazano<3,4-b>pyrazin
Indeno[1,2-b]furazano[3,4-E]pyrazin-9-one
9H-Indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazin-9-one
2-Oxa-1,3,4,10-tetraaza-cyclopenta[b]fluoren-9-one

Biological Activity

[Description]:

SMER3, a Rapamycin enhancer, is a selective Skp1-Cullin-F-box (SCF)Met30 ubiquitin ligase inhibitor. SMER3 enhances Rapamycin's growth inhibitory effect by inhibition of SCFMet30[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> E1/E2/E3 Enzyme

[In Vitro]

In yeast cells, Met4 ubiquitination is blocked in cells exposed to SMER3 (0-60 μM). The met4Δ cells are less susceptible to growth inhibition by SMER3[1]. Addition of SMER3 to the ligase reactions inhibited ubiquitination of Met4 by SCFMet30 in a dose-dependent manner. SMER3 significantly inhibits the binding of Met30 to Skp1, and does not affect the Skp1 and Met30 protein levels[1].

[References]

[1]. Mariam Aghajan, et al. Chemical genetics screen for enhancers of rapamycin identifies a specific inhibitor of an SCF family E3 ubiquitin ligase. Nat Biotechnol. 2010 Jul;28(7):738-42.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
437.2±55.0 °C at 760 mmHg

[ Melting Point ]:
296 °C(dec.)

[ Molecular Formula ]:
C₁₁H₄N₄O₂

[ Molecular Weight ]:
224.175

[ Flash Point ]:
218.2±31.5 °C

[ Exact Mass ]:
224.033432

[ PSA ]:
81.77000

[ LogP ]:
0.90

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.779

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Chemical genetics screen for enhancers of rapamycin identifies a specific inhibitor of an SCF family E3 ubiquitin ligase.

Nat. Biotechnol. 28 , 738 - 742, (2010)

The target of rapamycin (TOR) plays a central role in eukaryotic cell growth control. With prevalent hyperactivation of the mammalian TOR (mTOR) pathway in human cancers, strategies to enhance TOR pat...