| Identification | More | [Name]
7-Nitroindazole | [CAS]
2942-42-9 | [Synonyms]
7-NI
7-NITRO-1H-INDAZOLE
7-NITROINDAZOLE
INDAZOLE, 7-NITRO-
1H-Indazole, 7-nitro-
7-nitro-1h-indazol
7-NITROINDAZOLE INDAZOLE, 7-NITRO-INHIBI TOR OF BRAIN NI
NITROINDAZOLE
7-NITROINDAZOLE 97+% | [EINECS(EC#)]
220-934-4 | [Molecular Formula]
C7H5N3O2 | [MDL Number]
MFCD00022789 | [Molecular Weight]
163.13 | [MOL File]
2942-42-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [Melting point ]
185-186°C | [Boiling point ]
290.19°C (rough estimate) | [density ]
1.4141 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Soluble to 100 mM in DMSO and to 20 mM in ethanol | [form ]
powder to crystal | [pka]
10.03±0.40(Predicted) | [color ]
Light yellow to Brown | [Water Solubility ]
slightly soluble | [Usage]
A potent, selective brain inhibitor of mouse cerebellar Nitric Oxide Synthase. | [BRN ]
6809 | [InChI]
InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9) | [InChIKey]
PQCAUHUKTBHUSA-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2[N+]([O-])=O)C=N1 | [CAS DataBase Reference]
2942-42-9(CAS DataBase Reference) | [NIST Chemistry Reference]
7-Nitroindazole(2942-42-9) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R60:May impair fertility.
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
NK7962200
| [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Description]
7-Nitroindazole is a non-selective inhibitor of NOS isoforms in vitro. However, it shows good anti-nociceptive effects in vivo without affecting blood pressure via inhibition of eNOS.1 The IC50 values for inhibition of rat nNOS, bovine eNOS, and rat iNOS are 0.71, 0.78, and 5.8 μM, respectively.2 | [Chemical Properties]
yellow powder | [Uses]
A potent, selective brain inhibitor of mouse cerebellar Nitric Oxide Synthase. | [Uses]
NO synthetase inhibitor | [Definition]
7-Nitroindazole is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. It is a potent, selective brain inhibitor of mouse cerebellar Nitric Oxide Synthase, a hemoprotein enzyme that, in neuronal tissue, converts arginine to citrulline and nitric oxide (NO). | [Biological Activity]
Sodium salt of the non-selective NOS inhibitor 7-nitroindazole (7-Nitroindazole). | [Synthesis]
General procedure for the synthesis of 7-nitroindazole from 2-methyl-6-nitroaniline: To a stirred solution of 2-methyl-6-nitroaniline (10 g, 0.065 mol) in acetic acid (470 ml, 47 times the volume) was slowly added an aqueous solution (9 ml) of sodium nitrite (1.54 g, 0.06 mol, 1.1 equiv). The reaction mixture was stirred at room temperature for 30-45 min. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent 30% ethyl acetate/hexane, Rf=0.7). After completion of the reaction, acetic acid was removed by distillation under reduced pressure. The obtained residue was dissolved in ice water (200 ml), the precipitated solid was filtered, washed with cold water and dried under vacuum to afford the target product 7-nitroindazole as a yellow solid (10 g, 98% yield). | [References]
[1] Synlett, 2007, # 8, p. 1203 - 1206
[2] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 124; 125
[3] Archives of Pharmacal Research, 2018, vol. 41, # 1, p. 46 - 56
[4] European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 359 - 362
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 339 - 345 |
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