22876-21-7

Basic information

• Product Name: 5-NITRO BENZOXAZOLO-2-THIONE
• Synonyms: 5-NITRO BENZOXAZOLO-2-THIONE;5-Nitrobenzo[d]oxazole-2(3H)-thione;2(3H)-Benzoxazolethione,5-nitro-;5-Nitrobenzo[d]oxazole-2(3H)
• CAS NO: 22876-21-7
• Molecular Formula: C₇H₄N₂O₃S
• Molecular Weight: 196.18
• Mol File: 22876-21-7.mol
• Article Data: 26

Chemical Properties

• Melting Point: 244-245 °C
• Boiling Point: 326.7°Cat760mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 0.000213mmHg at 25°C
• Refractive Index: 1.741
• Storage Temp.: 2-8°C
• PKA: 8.90±0.20(Predicted)
• CAS DataBase Reference: 5-NITRO BENZOXAZOLO-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITRO BENZOXAZOLO-2-THIONE(22876-21-7)
• EPA Substance Registry System: 5-NITRO BENZOXAZOLO-2-THIONE(22876-21-7)

Safety Data

• Hazardous Substances Data: 22876-21-7(Hazardous Substances Data)

Usage

Description

5-NITRO BENZOXAZOLO-2-THIONE is an organic compound with the molecular formula C7H4N2O3S. It is a derivative of benzoxazole, which is a heterocyclic compound consisting of a benzene ring fused to an oxazole ring. The presence of a nitro group (-NO2) and a thione group (-C=S) in its structure gives it unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-NITRO BENZOXAZOLO-2-THIONE is used as a key intermediate compound for the synthesis of benzazole-substituted benzo-fused oxaheterocycle carboxamides. These carboxamides act as NOX4 inhibitors, which are important for the treatment of diseases involving impaired reactive oxygen species (ROS) generation, such as fibrosis.
In the development of NOX4 inhibitors, 5-NITRO BENZOXAZOLO-2-THIONE plays a crucial role in the formation of the final drug molecule. By targeting the NOX4 enzyme, these inhibitors can help regulate the production of ROS, which is often dysregulated in various pathological conditions, leading to tissue damage and fibrosis.

InChI:InChI=1/C7H4N2O3S/c10-9(11)4-1-2-6-5(3-4)8-7(13)12-6/h1-3H,(H,8,13)

Upstream product

• 137-26-8 Thiram 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 75-15-0 carbon disulfide 
• 7308-24-9 potassium thioxanthate 
• 3889-13-2 5-nitro-3H-benzooxazol-2-one 
• 51-28-5 2,4-Dinitrophenol 

Relevant articles and documents

Benzoheterocyclic amodiaquine analogues with potent antiplasmodial activity: Synthesis and pharmacological evaluation

The synthesis and evaluation of antiplasmodial activity of benzothiazole, benzimidazole, benzoxazole and pyridine analogues of amodiaquine is hereby reported. Benzothiazole and benzoxazole analogues with a protonatable tertiary nitrogen atom possessed excellent activity against the W2 and K1 chloroquine resistant strains of Plasmodium falciparum, with IC50s ranging from 7 to 22 nM.

Synthesis and evaluation of the anticonvulsant activities of 4-(2-(alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones

In this study, a novel series of 4-(2-(alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones (4a–m) was designed and synthesized. The anticonvulsant activities of these compounds were evaluated by using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure models in mice. The neurotoxicity of these compounds was evaluated using the rotarod neurotoxicity test. The majority of compounds showed anti-MES activities at 100 or 300 mg/kg. Compound 4g was considered to be the most promising, based on its potency against MES- and PTZ-induced seizures with ED50 values of 23.7 and 18.9 mg/kg, respectively. The TD50 value of 4g was 284.0 mg/kg, which resulted in a higher protective index (PI = TD50/ED50) value than that of carbamazepine and valproate. In an ELISA test, compound 4g significantly increased the γ-aminobutyric acid (GABA) content in mouse brain. In addition, pretreatment with thiosemicarbazide (an inhibitor of the GABA synthesizing enzyme) significantly decreased the activity of 4g in the MES model, which suggests that the mechanism through which compound 4g elicits its anticonvulsive action is at least in part through increasing the GABA level in the brain.

The discovery and optimization of a series of 2-aminobenzoxazole derivatives as ChemR23 inhibitors

A structural class of 2-aminobenzoxazole derivatives possessing biphenyltetrazole was discovered to be potent human ChemR23 inhibitors. We initially tried to improve the potency of compound 1, which was found through in-house screening using the human pla

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.