31083-55-3

Basic information

• Product Name: NSC 600157
• Synonyms: 2-(3-Pyridinylmethylene)-1H-indene-1,3(2H)-dione;2-(3-Pyridylmethylene)-1,3-indandione;NSC 600157;PRT4165;PRT 4165(NSC 600157)
• CAS NO: 31083-55-3
• Molecular Formula: C₁₅H₉NO₂
• Molecular Weight: 235.23746
• Mol File: 31083-55-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 377.63°C (rough estimate)
• Flash Point: 227°C
• Appearance: white to beige/
• Density: 1.1757 (rough estimate)
• Vapor Pressure: 2.26E-08mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble20mg/mL, clear
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: NSC 600157(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 600157(31083-55-3)
• EPA Substance Registry System: NSC 600157(31083-55-3)

Safety Data

• WGK Germany: 3
• RTECS: NK6710000
• Hazardous Substances Data: 31083-55-3(Hazardous Substances Data)

Usage

Description

NSC 600157, also known as PRT-4165, is a compound that functions as an inhibitor of Bmi1/Ring1A, which are subunits of the polycomb repressive complex 1 (PRC1). It is characterized by its ability to inhibit self-ubiquitination and block Bmi1/Ring1A-mediated ubiquitination, as well as drug-induced degradation of topoisomerase 2α. PRT-4165 also inhibits H2A/H2AX ubiquitination by blocking the E3 ubiquitin ligase activity of RNF2 and a Bmi1/RNF2 complex. NSC 600157 serves as a valuable tool for studying chromatin remodeling.

Uses

Used in Research Applications:
NSC 600157 is used as a research tool for studying the role of Bmi1/Ring1A in chromatin remodeling and the polycomb repressor complex (PRC) 1-mediated histone H2A ubiquitination. Its ability to inhibit the E3 ubiquitin ligase activity of RNF2 and the Bmi1/RNF2 complex makes it a valuable asset in understanding the underlying mechanisms of gene regulation and chromatin structure.
Used in Cancer Research:
NSC 600157 is used as a potential therapeutic agent in cancer research, particularly in the context of PRC1-mediated processes that may contribute to tumorigenesis. By inhibiting the Bmi1/Ring1A subunits, PRT-4165 may help to disrupt the abnormal chromatin remodeling that can lead to uncontrolled cell growth and the development of cancer.
Used in Drug Development:
NSC 600157 is used as a starting point for the development of new drugs targeting the polycomb repressive complex 1 (PRC1) and its role in various diseases, including cancer. Its ability to inhibit specific ubiquitination processes and disrupt the function of the Bmi1/RNF2 complex makes it a promising candidate for further investigation and optimization in drug discovery efforts.
Used in Epigenetic Studies:
NSC 600157 is used as a compound of interest in epigenetic research, focusing on the role of PRC1 in regulating gene expression and its potential implications in disease development. Understanding the molecular mechanisms by which PRT-4165 inhibits Bmi1/Ring1A and H2A/H2AX ubiquitination can provide insights into the broader field of epigenetics and the potential for targeted therapeutic interventions.

Biochem/physiol Actions

PRT4165 is a potent inhibitor of PRC1 (polycomb-repressive complex 1)-mediated histone H2A ubiquitylation in vivo and in vitro. PRT4165 inhibits the in vitro histone H2A E3 ubiquitin ligase activity of PRC1 components RING1, RNF2, and a BMI1/RNF2 complex. PRT4165 also inhibits DNA double-strand breaks induced ubiquitylation of histone H2AX.

References

1) Alchanati?et al. (2009),?The E3 ubiquitin-ligase Bmi1/Ring1A controls the proteasomal degradation of Top2alpha cleavage complex – a potentially new drug target; PLoS One,?4?e8104 2) Ismail?et al.?(2013),?A small molecule inhibitor of polycomb repressive complex 1 inhibits ubiquitin signaling at DNA double-strand breaks; J. Biol. Chem.,?288?26944

InChI:InChI=1/C15H9NO2/c17-14-11-5-1-2-6-12(11)15(18)13(14)8-10-4-3-7-16-9-10/h1-9H

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 606-23-5 1H-indene-1,3(2H)-dione 

Downstream Products

• 1607832-17-6 (E)-2-(2-oxo-2-phenyl-1-(pyridin-3-yl)ethylidene)-1H-indene-1,3(2H)-dione 

Relevant articles and documents

Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides

A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developedviabase-induced annulation. This efficient and simple protocol features simple operations, mild conditions and excellent functional group compatibility. A variety of structurally interesting spiro-cyclopropanes were prepared in excellent yields and diastereomeric ratios (up to 97% yield and 20?:?1 dr). Also, ring expansion of the cyclopropanation product to quickly deliver a complex indeno[1,2-c]pyridazine structure showcased an interesting application of this method.

Synthesis and thermal transformations of spiro-fused N- phthalimidoaziridines Dedicated to Professor Armin de Meijere on the occasion of his 75th birthday

Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3- diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2′-indene]-1′,3′-diones in good yields. Heating these aziridines with stan

REACTION PRODUCTS OF 1,3-INDANONE WITH HETEROAROMATIC CARBALDEHYDES: SYNTHESIS, STRUCTURE AND NMR-INVESTIGATIONS

The synthesis of 1:1 condensation products from 1,3-indadione and various heteroatomic carbaldehydes is described.Employment of aldehydes derived from ?-deficient N-heteroaromatics was found to lead also to 2:1 adducts via Michael-addition of the 1,3-dike