251649-40-8

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Nitro-4-(1H-pyrrol-1-yl)benzenol is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its unique structure allows for versatile chemical reactions, facilitating the creation of a wide range of therapeutic agents.
Used in Organic Chemistry:
In the realm of organic chemistry, 3-Nitro-4-(1H-pyrrol-1-yl)benzenol serves as a valuable building block for the synthesis of various organic compounds. Its reactivity and structural features make it suitable for use in a multitude of organic reactions, broadening the scope of chemical research and innovation.
Used in Antimicrobial Applications:
3-Nitro-4-(1H-pyrrol-1-yl)benzenol has demonstrated antibacterial and antifungal properties, positioning it as a potential candidate for the development of new antimicrobial agents. Its ability to combat microbial infections could be harnessed in the formulation of treatments for a variety of diseases caused by bacteria and fungi.
Used in Chemical Research:
3-Nitro-4-(1H-pyrrol-1-yl)benzenol is also employed in chemical research to explore its properties and potential applications. Its unique structure and reactivity make it an interesting subject for study, contributing to the advancement of knowledge in the field of chemistry.

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 
• 1228182-66-8 3-amino-4-(1H-pyrrol-1-yl)phenol 

Relevant academic research and scientific papers

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.

SMALL MOLECULES INHIBITORS OF RAD51

Embodiments concern methods and small molecule compositions for selectively inhibiting RAD51-mediated D-loop formation while preserving RAD51's ability to form nucleoprotein filaments. The selective RAD51 D-loop formation activity inhibitors DNA repair while minimizing replication-associated toxicity in normal tissue.

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

Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists: Synthesis, further structure-activity relationships, and biological studies

The synthesis, pharmacological evaluation, and structure-activity relationships (SARs) of a series of novel pyrroloquinoxalines and heteroaromatic-related derivatives are described. The new pyrroloquinoxaline- related ligands were tested in rat cortex, a tissue expressing high density of 5-HT3 receptors, and on NG108-15 cells and exhibited IC50 values in the low nanomolar or subnanomolar range, as measured by the inhibition of [3H]zacopride binding. The SAR studies detailed herein delineated a number of structural features required for improving affinity. Some of the ligands were employed as 'molecular yardsticks' to probe the spatial dimensions of the lipophilic pockets L1, L2, and L3 in the 5-HT3 receptor cleft, while the 7-OH pyrroloquinoxaline analogue was designed to investigate hydrogen bonding with a putative receptor site H1 possibly interacting with the serotonin hydroxy group. The most active pyrroloquinoxaline derivatives showed subnanomolar affinity for the 5-HT3 receptor. In functional studies ([14C]guanidinium accumulation test in NG108-15 hybrid cells, in vitro) most of the tested compounds showed clear-cut 5-HT3 agonist properties, while some others were found to be partial agonists. Several heteroaromatic systems, bearing N-substituted piperazine moieties, have been explored with respect to 5-HT3 affinity, and novel structural leads for the development of potent and selective central 5-HT3 receptor agonists have been identified. Preliminary pharmacokinetic studies indicate that these compounds easily cross the blood brain barrier (BBB) after systemic administration with a brain/plasma ratio between 2 and 20, unless they bear a highly hydrophilic group on the piperazine ring. None of the tested compounds showed in vivo anxiolytic-like activity, but potential analgesic-like properties have been possibly disclosed for this new class of 5-HT3 receptor agonists.