924296-39-9

Basic information

• Product Name: 7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile
• Synonyms: 7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile;HBX 41108;7-chloro-5-oxo-5H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile;7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile HBX 41108
• CAS NO: 924296-39-9
• Molecular Formula: C13H3ClN4O
• Molecular Weight: 266.64212
• Product Categories: Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 924296-39-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220(dec.)℃
• Boiling Point: 604.9°C at 760 mmHg
• Flash Point: 319.6°C
• Appearance: /
• Density: 1.66
• Vapor Pressure: 1.39E-14mmHg at 25°C
• Refractive Index: 1.725
• Solubility: insoluble in H2O; ≥1.83 mg/mL in EtOH with gentle warming and ultrasonic; ≥13.35 mg/mL in DMSO
• CAS DataBase Reference: 7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile(924296-39-9)
• EPA Substance Registry System: 7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile(924296-39-9)

Safety Data

• Hazardous Substances Data: 924296-39-9(Hazardous Substances Data)

Usage

Description

7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile is a chemical compound that serves as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. It is characterized by its unique molecular structure, which includes a chloro substituent, an oxo group, and two dicyano groups attached to an indeno[1,2-b]pyrazine core.

Uses

Used in Pharmaceutical Industry:
7-Chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile is used as a synthetic intermediate for the development of 9-Oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile analogues. These analogues are evaluated for their potential as inhibitors of deubiquitinating enzymes, which play a crucial role in various cellular processes, including protein degradation and signal transduction. By targeting these enzymes, these analogues may offer therapeutic benefits in the treatment of various diseases, such as cancer and neurodegenerative disorders.

Biological Activity

hbx 41108 is a potent inhibitor of usp7 with ic50 value of 424 nm [1].ubiquitin-specific-processing protease 7 (usp7) is a ubiquitin specific protease and removes ubiquitin from specific protein substrates. usp7 can deubiquitinate p53, protecting p53 from mdm2-mediated degradation and involving the oncogenic stabilization of p53.hbx 41108 is an uncompetitive and reversible usp7 inhibitor. hbx 41108 inhibited usp7-mediated p53 deubiquitination with ic50 value of 0.8 μm in a dose-dependent way and was only weakly active against the aspartic, serine and metalloproteases tested with ic50 > 10 μm. in hct116 cells, hbx 41108 increased the levels of p53 and p21cip1/waf, which was the product of p53 target genes. in hek293 cells, hbx 41108 increased the level of polyubiquitinated forms of p53 and reduced mdm2 levels. in hct116 colon cancer cells, hbx 41108 inhibited cell proliferation with ic50 value of 1 μm in a dose-dependent way and induced apoptosis in a dose-dependent manner [1]. in cos7 cells, hbx 41108 inhibited pparγ stability induced by usp7 and decreased the basal transcriptional activity of pparγ by 70% [2].

references

[1]. colland f, formstecher e, jacq x, et al. small-molecule inhibitor of usp7/hausp ubiquitin protease stabilizes and activates p53 in cells. mol cancer ther, 2009, 8(8): 2286-2295. [2]. lee kw, cho jg, kim cm, et al. herpesvirus-associated ubiquitin-specific protease (hausp) modulates peroxisome proliferator-activated receptor γ (pparγ) stability through its deubiquitinating activity. j biol chem, 2013, 288(46): 32886-32896.

InChI:InChI=1/C13H3ClN4O/c14-6-1-2-7-8(3-6)13(19)12-11(7)17-9(4-15)10(5-16)18-12/h1-3H

Upstream product

• 1223532-25-9 C₁₃H₅ClN₄ 
• 1187-42-4 diaminomaleonitrile 
• 207554-23-2 5-chloro-1,2-indanedione 

Relevant articles and documents

Synthesis and biological evaluation of 9-oxo-9hindeno[1,2-b]pyrazine-2,3- dicarbonitrile analogues as potential inhibitors of deubiquitinating enzymes

High-throughput screening highlighted 9-oxo-9H-indeno[1,2-b]pyrazine-2,3- dicarbonitrile (1) as an active inhibitor of ubiquitin-specific proteases (USPs), a family of hydrolytic enzymes involved in the removal of ubiquitin from protein substrates. The chemical behavior of compound 1 was examined. Moreover, the synthesis and in vitro evaluation of new compounds, analogues of 1, led to the identification of potent and selective inhibitors of the deubiquitinating enzyme USP8.

Novel cysteine protease inhibitors and their therapeutic applications

The present invention concerns new compounds of formula (I), their process of preparation and their therapeutic use.