5228-61-5

Basic information

• Product Name: 5-bromo-2-nitrobenzenamine
• Synonyms: 5-bromo-2-nitrobenzenamine;2-Amino-4-bromonitrobenzene;(5-BroMo-2-nitrophenyl)aMine;BenzenaMine, 5-broMo-2-nitro-;5-bromo-2-nitroanline
• CAS NO: 5228-61-5
• Molecular Formula: C₆H₅BrN₂O₂
• Molecular Weight: 217.02
• Mol File: 5228-61-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 151-152 °C
• Boiling Point: 331.9 °C at 760 mmHg
• Flash Point: 154.6 °C
• Appearance: /
• Density: 1.812 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -1.53±0.25(Predicted)
• CAS DataBase Reference: 5-bromo-2-nitrobenzenamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-nitrobenzenamine(5228-61-5)
• EPA Substance Registry System: 5-bromo-2-nitrobenzenamine(5228-61-5)

Safety Data

• Hazardous Substances Data: 5228-61-5(Hazardous Substances Data)

Usage

General Description

5-bromo-2-nitrobenzenamine is a chemical compound with the molecular formula C6H4BrNO2. It is a nitroamine that contains a bromine atom and a nitro group on a benzene ring. 5-bromo-2-nitrobenzenamine is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. It has also been studied for its potential use in organic chemical reactions and as a reagent in organic synthesis. 5-bromo-2-nitrobenzenamine is known to be harmful if ingested, inhaled, or absorbed through the skin, and proper safety precautions should be taken when handling this chemical.

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Relevant articles and documents

Sulfide Analogues of Flupirtine and Retigabine with Nanomolar KV7.2/KV7.3 Channel Opening Activity

The potassium channel openers flupirtine and retigabine have proven to be valuable analgesics or antiepileptics. Their recent withdrawal due to occasional hepatotoxicity and tissue discoloration, respectively, leaves a therapeutic niche unfilled. Metabolic oxidation of both drugs gives rise to the formation of electrophilic quinones. These elusive, highly reactive metabolites may induce liver injury in the case of flupirtine and blue tissue discoloration after prolonged intake of retigabine. We examined which structural features can be altered to avoid the detrimental oxidation of the aromatic ring and shift oxidation toward the formation of more benign metabolites. Structure–activity relationship studies were performed to evaluate the KV7.2/3 channel opening activity of 45 derivatives. Sulfide analogues were identified that are devoid of the risk of quinone formation, but possess potent KV7.2/3 opening activity. For example, flupirtine analogue 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50=1.4 nm), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

Importance of 5/6-aryl substitution on the pharmacological profile of 4?-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1?-biphenyl]-2-carboxylic acid derived PPARγ agonists

In this structure-activity relationship study, the influence of aryl substituents at position 5 or 6 on the pharmacological profile of the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1‘-biphenyl]-2-carboxylic acid was investigated. This lead was previously identified as the essential part of telmisartan to induce PPARγ activation. Para-OCH3-phenyl substitution strongly increased potency and efficacy independent of the position. Both compounds represent full agonists because of strong hydrophobic contacts with the amino acid Phe363 in the ligand binding domain. Partial agonists with higher potency than telmisartan or the lead were obtained with OH or Cl substituents at the phenyl ring. Molecular modeling suggested additional hydrogen or halogen bonds with Phe360 located at helix 7. It is assumed that these interactions fix helix 7, thereby promoting a partial agonist conformation of the receptor. The theoretical considerations correlate very well with the results from the luciferase transactivation assay using hPPARγ-LBD as well as those from a time-resolved fluorescent resonance energy transfer (TR-FRET) assay in which the coactivator (TRAP220, PGC-1α) recruitment and corepressor (NCoR1) release pattern was investigated.

NOVEL TRICYCLIC COMPOUNDS AS INHIBITORS OF MUTANT IDH ENZYMES

The present invention is directed to tricyclic compounds of formula (I) which are inhibitors of one or more mutant IDH enzymes: (I). The present invention is also directed to uses of the tricyclic compounds described herein in the potential treatment or prevention of cancers in which one or more mutant IDH enzymes are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such cancers.