7-Nitroindazole

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7-Nitroindazole

7-Nitroindazole | 2942-42-9

Catalog Number A03-0007
Category Nitric Oxide (NO) & Reactive Oxygen Species (ROS)
Molecular Formula C7H5N3O2
Molecular Weight 163.14
Catalog Number Size Price Quantity
A03-0007 -- $--

Product Introduction

7-Nitroindazole is a nitric oxide synthase inhibitor.

Chemical Information

Synonyms 7-Nitroindazole (7-NI);1H-Indazole, 7-nitro-; NSC 72843
Purity ≥98% by HPLC
IUPAC Name 7-nitro-1H-indazole
Canonical SMILES C1=CC2=C(C(=C1)[N+](=O)[O-])NN=C2
InChI InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9)
InChI Key PQCAUHUKTBHUSA-UHFFFAOYSA-N
Solubility Soluble in DMSO (Slightly), Methanol (Slightly)
Density 1.525±0.06 g/cm3
Appearance Pale Yellow to Yellow Solid
Boiling Point 383.3±15.0°C at 760 mmHg
Melting Point 186.5-187.5°C
  • Product Specification
  • Application
Storage Store at -20°C
Signal Danger
GHS Hazard Statements H301 (86.67%): Toxic if swallowed [Danger Acute toxicity, oral] H315 (11.11%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (97.78%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H341 (11.11%): Suspected of causing genetic defects [Warning Germ cell mutagenicity] H351 (86.67%): Suspected of causing cancer [Warning Carcinogenicity] H360 (86.67%): May damage fertility or the unborn child [Danger Reproductive toxicity]
Precautionary Statement Codes P203, P264, P264+P265, P270, P280, P281, P301+P316, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

7-Nitroindazole is a chemical compound that belongs to the class of nitroarenes and is characterized by its nitro group attached to an indazole ring at the 7-position. Known chemically as 7-nitro-1H-indazole, it inhibits the enzyme neuronal nitric oxide synthase (nNOS), which plays a significant role in producing nitric oxide in neuronal tissues. This inhibition hinders the conversion of L-arginine to nitric oxide, thereby affecting cell signaling mechanisms which depend on nitric oxide as a signaling molecule.

One of the primary applications of 7-Nitroindazole is its potential use in neuroprotection. Due to its ability to inhibit nNOS, it is being studied for its protective effects against neurodegenerative diseases and conditions characterized by excitotoxicity. By mitigating oxidative stress and reducing the formation of harmful peroxynitrites, 7-Nitroindazole shows promise in protecting nerve cells from damage. This has implications for diseases like Alzheimer’s and Parkinson’s, where oxidative stress and excitotoxic damage are significant concerns.

Another key application of 7-Nitroindazole is in the field of anticonvulsant therapy. Studies suggest that it possesses anticonvulsive properties that do not rely solely on nNOS inhibition, indicating it may modulate neuronal activity through different mechanisms. This property provides a basis for research into its potential as a treatment for seizure disorders such as epilepsy, where it might offer benefits as part of combination therapies.

7-Nitroindazole also finds its use in research settings, particularly concerning cardiovascular studies. Its role in modulating nitric oxide production offers insights into vasodilation and blood pressure regulation, making it a valuable tool in studying cardiovascular function and potential pharmaceutical interventions. Researchers use it to understand better how nitric oxide pathways influence heart and blood vessel conditions, aiming to develop more precise treatments for hypertension and related diseases.

Lastly, 7-Nitroindazole’s inhibition of nitric oxide synthase makes it a point of interest in cancer research. Since nitric oxide serves as a signaling molecule that can influence tumor growth and metastasis, regulating its synthesis with compounds like 7-Nitroindazole could offer new strategies in cancer therapy. Investigations focus on its potential to reduce tumor progression and enhance the efficacy of existing cancer treatments by disrupting the tumor microenvironment and signaling pathways that rely on nitric oxide.

Computed Properties

Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 0
Exact Mass 163.038176411 g/mol
Monoisotopic Mass 163.038176411 g/mol
Topological Polar Surface Area 74.5Ų
Heavy Atom Count 12
Formal Charge 0
Complexity 192
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
36162621 2022-10-01 N-isopropylbenzylamine, a methamphetamine mimics, produces toxicity via increasing nitric oxide in vitro Toxicology
23571415 2013-06-01 Structure-based identification of OATP1B1/3 inhibitors Molecular pharmacology
22879052 2013-01-01 Renal oxygenation and function of the rat kidney: effects of inspired oxygen and preglomerular oxygen shunting Advances in experimental medicine and biology
22877786 2012-12-01 7-Nitroindazole down-regulates dopamine/DARPP-32 signaling in neostriatal neurons in a rat model of Parkinson's disease Neuropharmacology
22884925 2012-12-01 The differential role of NOS inhibitors on stress-induced anxiety and neuroendocrine alterations in the rat Behavioural brain research

Patents

Publication NumberTitlePriority Date
CN-114146092-A Hyaluronic acid fragment, application of preparation thereof and quality control activity detection method 2021-11-15
CN-113912542-A Method for directly ammoniating nitro nitrogen heterocyclic compound 2021-10-09
WO-2022239001-A1 Pharmaceutical compositions for treating neurological conditions 2021-05-10
US-2022331395-A1 Extended-release injectable gel formulations containing angiotensin-(1-7) oligopeptides or variants thereof 2021-04-07
WO-2022216941-A1 Extended-release injectable gel formulations containing angiotensin-(1-7) oligopeptides or variants thereof 2021-04-07
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