68008-91-3

Basic information

• Product Name: Imidazo[1,2-a]quinoxaline, 4-(4-nitrophenyl)-
• CAS NO: 68008-91-3
• Molecular Formula: C16H10N4O2
• Molecular Weight: 290.281
• Mol File: 68008-91-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Imidazo[1,2-a]quinoxaline, 4-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazo[1,2-a]quinoxaline, 4-(4-nitrophenyl)-(68008-91-3)
• EPA Substance Registry System: Imidazo[1,2-a]quinoxaline, 4-(4-nitrophenyl)-(68008-91-3)

Safety Data

• Hazardous Substances Data: 68008-91-3(Hazardous Substances Data)

Upstream product

• 23309-16-2 1-(2-nitrophenyl)-1H-imidazole 
• 88-73-3 2-Chloronitrobenzene 
• 24067-17-2 4-nitrophenylboronic acid 
• 191349-69-6 4-chloroimidazo[1,2-a]quinoxaline 

Downstream Products

• 68008-93-5 4-(imidazo[1,2-a]quinoxalin-4-yl)aniline 

Relevant articles and documents

Optimization of Drug Candidates That Inhibit the D-Loop Activity of RAD51

RAD51 is the central protein in homologous recombination (HR) repair, where it first binds ssDNA and then catalyzes strand invasion via a D-loop intermediate. Additionally, RAD51 plays a role in faithful DNA replication by protecting stalled replication forks; this requires RAD51 to bind DNA but may not require the strand invasion activity of RAD51. We previously described a small-molecule inhibitor of RAD51 named RI(dl)-2 (RAD51 inhibitor of D-loop formation #2, hereafter called 2 h), which inhibits D-loop activity while sparing ssDNA binding. However, 2 h is limited in its ability to inhibit HR in vivo, preventing only about 50 % of total HR events in cells. We sought to improve upon this by performing a structure–activity relationship (SAR) campaign for more potent analogues of 2 h. Most compounds were prepared from 1-(2-aminophenyl)pyrroles by forming the quinoxaline moiety either by condensation with aldehydes, then dehydrogenation of the resulting 4,5-dihydro intermediates, or by condensation with N,N′-carbonyldiimidazole, chlorination, and installation of the 4-substituent through Suzuki–Miyaura coupling. Many analogues exhibited enhanced activity against human RAD51, but in several of these compounds the increased inhibition was due to the introduction of dsDNA intercalation activity. We developed a sensitive assay to measure dsDNA intercalation, and identified two analogues of 2 h that promote complete HR inhibition in cells while exerting minimal intercalation activity.

1-(2-Phenylureylene)imidazoles

A 1-(2-acylaminophenyl)imidazole of formula: STR1 wherein R2 is hydrogen or a radical bonded to the nitrogen by a carbon to nitrogen linkage and selected from the group consisting of aliphatic, cycloaliphatic, phenyl, substituted phenyl, fused bicyclic aryl, and monocyclic aryl substituted aliphatic groups.