41443-28-1

Basic information

• Product Name: ODQ
• Synonyms: ODQ;2-OXA-3,5,9B-TRIAZA-CYCLOPENTA[A]NAPHTHALENE-1-ONE;1H-[1,2,4]OXADIAZOLE[4,3-A]QUINOXALIN-1-ONE;1H-[1,2,4]OXADIAZOLO[4,3-A]QUINOXALIN-1-ONE;1H-[1,2,4]OXADIAZOLO[4,3-A]QUINOXALIN-1-ONE[ODQ];ODQ,98%;ODQ1H-[1,2,4]Oxadiazole[4,3-a]quinoxalin-1-one;1H-[1,2,4]Oxadiazolo[4,3-A]quinoxalin-1-one (9ci)
• CAS NO: 41443-28-1
• Molecular Formula: C9H5N3O2
• Molecular Weight: 187.15
• Product Categories: Cyclic Nucleotide related;Signalling;Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Antineoplastic
• Mol File: 41443-28-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 160-170 °C
• Boiling Point: 321.89°C (rough estimate)
• Flash Point: 148.1 °C
• Appearance: pale yellow/powder
• Density: 1.3753 (rough estimate)
• Vapor Pressure: 0.000301mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: 1.2 mg/mL
• PKA: 0.94±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: ODQ(CAS DataBase Reference)
• NIST Chemistry Reference: ODQ(41443-28-1)
• EPA Substance Registry System: ODQ(41443-28-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RO0913150
• Hazardous Substances Data: 41443-28-1(Hazardous Substances Data)

Usage

Description

1h-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one, also known as ODQ, is a potent and selective inhibitor of soluble guanylyl cyclase (sGC) with an IC50 value of 20 nM. It is an off-white to yellow powder that acts by competing with nitric oxide (NO) for the heme site of sGC, binding irreversibly. ODQ is a valuable tool for investigating the role of the NO-cGMP pathway in cellular signaling and physiological processes.

Uses

Used in Pharmaceutical Research:
1h-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one is used as a research compound for studying the NO-cGMP pathway in various cellular signaling and physiologic processes. Its potent and selective inhibition of sGC makes it an essential tool in understanding the underlying mechanisms of this pathway.
Used in Neuroscience Research:
In the field of neuroscience, 1h-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one is used as a chemical agent to inhibit neurite outgrowth and cause neurite retraction in PC12 cells. This effect is observed independently of its action on soluble guanylyl cyclase, making it a useful compound for studying neuronal development and growth.
Used in Drug Development:
ODQ's selective inhibition of sGC makes it a potential candidate for the development of drugs targeting the NO-cGMP pathway. This pathway is involved in various physiological processes, and modulating its activity could have therapeutic applications in treating conditions related to this pathway's dysregulation.

Biological Activity

ODQ is a potent and selective inhibitor of NO-sensitive guanylyl cyclase.

Biochem/physiol Actions

H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one (ODQ) non competitively inhibits the action of nitric oxide-sensitive guanylyl cyclase and results in a supposedly irreversible oxidation of the prosthetic heme group. ODQ has been used to study the role of cyclic guanosine monophosphate (cGMP) pathway in nitric oxide (NO) signal transduction.

References

1) Garthwaite?et al.?(1995),?Potent and Selective Inhibition of Nitric Oxide-sensitive Guanylyl Cyclase by 1H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one; Mol. Pharmacol.?48?184 2) Schrammel?et al.?(1996),?Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase; Mol. Pharmacol.?50?1 3) Estevez?et al.?(1998),?Nitric oxide-dependent production of cGMP supports the survival of rat embryonic motor neurons cultured with brain-derived neurotrophic factor; J. Neurosci.?18?3708 4) Vandecasteele?et al.?(1998),?Role of the NO-cGMP in the muscarinic regulation of the L-type Ca2+ current in human atrial myocytes; J. Physiol.?506?653 5) Martins-Pinge?et al.?(1999),?Nitric oxide-dependent guanylyl cyclase participates in the glutamatergic neurotransmission within the rostral ventrolateral medulla of awake rats;?Hypertension?34?748

InChI:InChI=1/C9H5N3O2/c13-9-12-7-4-2-1-3-6(7)10-5-8(12)11-14-9/h1-5H

Upstream product

• 36003-81-3 3,4-dihydro-2(1H)-quinoxalinoneoxime 
• 41443-27-0 quinoxaline(1H)-2-one oxime 
• 530-62-1 1,1'-carbonyldiimidazole 
• 36002-67-2 1-Oxo-4,5-dihydro-<1.2.4>oxadiazolo<4.3-a>chinoxalin 

Relevant articles and documents

Suzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analogues

Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1′-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised.