168123-82-8

Basic information

• Product Name: 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE
• Synonyms: 7-Bromo-2,3-dioxo-1,4-dihydro-pyrido[2,3-b]pyrazine;7-broMo-1H,2H,3H,4H-pyrido[2,3-b]pyrazine-2,3-dione;7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE;7-bromo-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione
• CAS NO: 168123-82-8
• Molecular Formula: C7H2BrN3O2
• Molecular Weight: 240.01
• Mol File: 168123-82-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 527 °C at 760 mmHg
• Flash Point: 272.5 °C
• Appearance: /
• Density: 1.851 g/cm³
• Vapor Pressure: 1E-11mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE(168123-82-8)
• EPA Substance Registry System: 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE(168123-82-8)

Safety Data

• Hazardous Substances Data: 168123-82-8(Hazardous Substances Data)

Usage

General Description

7-Bromopyrido[2,3-b]pyrazine-2,3(1H,4H)-dione is a chemical compound with the molecular formula C8H4BrN3O2. It is a heterocyclic compound containing a pyrido[2,3-b]pyrazine ring system with a bromine substituent and a dione functional group. It is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE has potential applications in the pharmaceutical industry due to its ability to act as an effective building block in the synthesis of various biologically active compounds. Additionally, 7-Bromopyrido[2,3-b]pyrazine-2,3(1H,4H)-dione is also used as a reagent in organic chemical reactions and as a research tool in the study of heterocyclic chemistry.

InChI:InChI=1/C7H4BrN3O2/c8-3-1-4-5(9-2-3)11-7(13)6(12)10-4/h1-2H,(H,10,12)(H,9,11,13)

Upstream product

• 38875-53-5 5-bromo-pyridine-2,3-diamine 
• 144-62-7 oxalic acid 
• 95-92-1 oxalic acid diethyl ester 
• 6945-68-2 5-bromo-3-nitro-pyridin-2-ylamine 

Relevant articles and documents

Discovery of a Novel Highly Selective Histamine H4 Receptor Antagonist for the Treatment of Atopic Dermatitis

The histamine H4 receptor (H4R), a member of the G-protein coupled receptor family, has been considered as a potential therapeutic target for treating atopic dermatitis (AD). A large number of H4R antagonists have been disclosed, but no efficient agents controlling both pruritus and inflammation in AD have been developed yet. Here, we have discovered a novel class of orally available H4R antagonists showing strong anti-itching and anti-inflammation activity as well as excellent selectivity against off-targets. A pharmacophore-based virtual screening system constructed in-house successfully identified initial hit compound 9, and the subsequent homology model-guided optimization efficiently led us to discover pyrido[2,3-e]tetrazolo[1,5-a]pyrazine analogue 48 as a novel chemotype of a potent and highly selective H4R antagonist. Importantly, orally administered compound 48 exhibits remarkable efficacy on antipruritus and anti-inflammation with a favorable pharmacokinetic (PK) profile in several mouse models of AD. Thus, these data strongly suggest that our compound 48 is a promising clinical candidate for treatment of AD.

Discovery and analgesic evaluation of 8-chloro-1,4-dihydropyrido[2,3- b ]pyrazine-2,3-dione as a novel potent d -amino acid oxidase inhibitor

A series of 5-azaquinoxaline-2,3-dione derivatives were synthesized and evaluated on d-amino acid oxidase (DAAO) inhibition as potential α-hydroxylactam-based inhibitors. The potent inhibitory activities in vitro suggested that 5-nitrogen could significantly enhance the binding affinity by strengthening relevant hydrogen bond interactions. The analgesic effects of intrathecal and systemic injection of 8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione, a representative molecule of 5-azaquinoxaline-2,3-dione, were investigated in rodents. This research not only confirmed the analgesic effect of the DAAO inhibitors but provided a new class of chemical entities with oral application potential for the treatment of chronic pain and morphine analgesic tolerance.

5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: Novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors

A group of 5-aza-7-substituted-1,4-dihydroquinoxaline-2,3-diones (QXs) and the corresponding 5-(N. oxyaza)-7-substituted QXs were prepared and evaluated as antagonists of ionotropic glutamate receptors. The in vitro potency of these QXs was determined by inhibition of [3H]-5,7- dichlorokynurenic acid ([3H]DCKA) binding to N-methyl-D-aspartate (NMDA)/glycine receptors, [3H]-(S)-α-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid ([3H]AMPA) binding to AMPA receptors, and [3H]kainate ([3H]KA) binding to KA receptors in rat brain membranes. 5-(N- Oxyaza)-QXs 12a-e all have low micromolar or submicromolar potency for NMDA/glycine receptors and low micromolar potencies for AMPA and KA receptors. QXs 12a-e display 2-12-fold selectivity for NMDA/glycine receptors compared to AMPA receptors, and ~2-fold difference between AMPA and KA potency. In contrast to other QXs that either show high selectivity for NMDA (such as ACEA 1021) or AMPA (such as NBQX) receptors, these molecules are broad spectrum antagonists of ionotropic glutamate receptors. 7-Nitro-5-(N- axyaza)-QX (12e) is the most potent inhibitor among 12a-e, having IC50 values of 0.69, 1.3, and 2.4 μM at NMDA, AMPA, and KA receptors, respectively. In functional assays on glutamate receptors expressed in oocytes by rat cerebral cortex poly(A+) RNA, 7-chloro-5-(N-oxyaza)-QX (12a) and 7-nitro-5(N-oxyaza)-QX (12e) have K(b) values of 0.63 and 0.31 μM for NMDA/glycine receptors, and are 6- and 4-fold selective for NMDA over AMPA receptors, respectively. 5-(N-Oxyaza)-7-substituted-QXs 12a-e all have surprisingly high in vivo potency as anticonvulsants in a mouse maximal electroshock-induced seizure (MES) model. 7-Chloro-5-(N-oxyaza)-QX (12a), 7- bromo-5-(N-oxyaza)-QX (12b), and 7-methyl-5-(N-oxyaza)-QX (12c) have ED50 values of 0.82, 0.87, and 0.97 mg/kg iv, respectively. The high in vivo potency of QXs 12a-e is particularly surprising given their low log P values (~ -2.7). Separate studies indicate that QXs 12a and 12e are also active in vive as neuroprotectants and also have antinociceptive activity in animal pain models. In terms of in vivo activity, these 5-(N-oxyaza)-7-substituted- QXs are among the most potent broad spectrum ionotropic glutamate antagonists reported.