251649-40-8

Basic information

• Product Name: 3-Nitro-4-(1H-pyrrol-1-yl)benzenol
• Synonyms: 3-Nitro-4-(1H-pyrrol-1-yl)benzenol
• CAS NO: 251649-40-8
• Molecular Formula: C₁₀H₈N₂O₃
• Molecular Weight: 204
• Mol File: 251649-40-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.5±37.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: 6.75±0.14(Predicted)
• CAS DataBase Reference: 3-Nitro-4-(1H-pyrrol-1-yl)benzenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitro-4-(1H-pyrrol-1-yl)benzenol(251649-40-8)
• EPA Substance Registry System: 3-Nitro-4-(1H-pyrrol-1-yl)benzenol(251649-40-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 251649-40-8(Hazardous Substances Data)

Usage

General Description

3-Nitro-4-(1H-pyrrol-1-yl)benzenol, also known as 3-Nitro-2-pyrrolphenol, is a chemical compound with the molecular formula C10H8N2O3. It is a yellowish crystalline solid with a nitro group and a pyrrole ring in its structure. 3-Nitro-4-(1H-pyrrol-1-yl)benzenol is used in the synthesis of pharmaceuticals and organic compounds, and it also has applications in the field of organic chemistry. Additionally, it has been found to exhibit antibacterial and antifungal properties, making it potentially useful in the development of new antimicrobial agents. However, it is important to handle this compound with caution, as it may be harmful if ingested or inhaled, and it can cause irritation to the skin and eyes.

Upstream product

• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 610-81-1 4-hydroxy-2-nitroaniline 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 

Downstream Products

• 251649-41-9 1-(4-benzyloxy-2-nitrophenyl)-1H-pyrrole 
• 251649-46-4 1-(2-amino-4-benzyloxyphenyl)-1H-pyrrole 
• 251649-49-7 7-(benzyloxy)pyrrolo[1,2-a]quinoxalin-4(5H)-one 
• 251649-57-7 7-benzyloxy-4-chloropyrrolo[1,2-a]quinoxaline 
• 251649-71-5 7-benzyloxy-4-(4-methyl-piperazin-1-yl)-pyrrolo[1,2-a]quinoxaline 
• 1228182-66-8 3-amino-4-(1H-pyrrol-1-yl)phenol 

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.

Development of Small Molecules that Specifically Inhibit the D-loop Activity of RAD51

RAD51 is the central protein in homologous recombination (HR) DNA repair and represents a therapeutic target in oncology. Herein we report a novel class of RAD51 inhibitors that were identified by high throughput screening. In contrast to many previously