16004-43-6

Usage

Uses

Used in Analytical Chemistry:
2-Nitrobenzaldehyde Semicarbazone is used as a derivatization agent for the assay of nitrofurans in animal tissue. Its application is based on its ability to form stable complexes with nitrofurans, which can then be detected and quantified using various analytical techniques such as high-performance liquid chromatography (HPLC) or gas chromatography-mass spectrometry (GC-MS). This allows for the accurate determination of nitrofuran residues in animal tissues, which is important for ensuring food safety and compliance with regulatory standards.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Nitrobenzaldehyde Semicarbazone is used as a labeled derivatized standard for the assay of nitrofurans in animal tissue. This application is crucial for the development and validation of analytical methods for detecting and quantifying nitrofuran residues in pharmaceutical products, ensuring the quality and safety of these products for human and veterinary use.

InChI:InChI=1/C8H8N4O3/c9-8(13)11-10-5-6-3-1-2-4-7(6)12(14)15/h1-5H,(H3,9,11,13)/b10-5+

Upstream product

• 1929-19-7 bis-(2-nitro-benzylidene)-hydrazine 
• 563-41-7 semicarbazide hydrochloride 
• 127-08-2 potassium acetate 
• 4426-72-6 hydrazine carboxamide 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 552-89-6 2-nitro-benzaldehyde 
• 23102-23-0 3-(2-nitrophenyl)-4H-1,2,4-triazol-5-ol 
• 109060-71-1 2-amino-5-(2'-nitrophenyl)-1,3,4-oxadiazole 
• 553-74-2 nitrin 
• 610-64-0 1-(2-nitrobenzylidene)-2-phenylhydrazine 

Relevant academic research and scientific papers

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide

A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.

Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking studies of 2-amino-1,3,4-oxadiazole derivatives

Background: In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds. Methods: 1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as1 H-,13 C-NMR and HREI-MS. Results: The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM. Conclusion: Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.

Semicarbazone derivatives as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

A series of hydrazinecarboxamide derivatives were synthesized and examined against urease for their inhibitory activity. Among the series, the 1-(3-fluorobenzylidene)semicarbazide (4a) (IC50 = 0.52 ± 0.45 μM), 4u (IC50 = 1.23 ± 0.32 μM) and 4h (IC50 = 2.22 ± 0.32 μM) were found most potent. Furthermore, the molecular docking study was also performed to demonstrate the binding mode of the active hydrazinecarboxamide with the enzyme, urease. In order to estimate drug likeness of compounds, in silico ADME evaluation was carried out. All compounds exhibited favorable ADME profiles with good predicted oral bioavailability.

Plant Uptake and Metabolism of Nitrofuran Antibiotics in Spring Onion Grown in Nitrofuran-Contaminated Soil

Environmental pollution caused by the discharge of mutagenic and carcinogenic nitrofurans to the aquatic and soil environment is an emerging public health concern because of the potential in producing drug-resistant microbes and being uptaken by food crops. Using liquid chromatography-tandem mass spectrometry analysis and with spring onion (Allium wakegi Araki) as the plant model, we investigated in this study the plant uptake and accumulation of nitrofuran from a contaminated environment. Our study revealed for the first time high uptake and accumulation rates of nitrofuran in the edible parts of the food crop. Furthermore, results indicated highly efficient plant metabolism of the absorbed nitrofuran within the plant, leading to the formation of genotoxic hydrazine-containing metabolites. The results from this study may disclose a previously unidentified human exposure pathway through contaminated food crops.

Synthesis, characterization and biological activities of semicarbazones and their copper complexes

Substituted semicarbazones/thiosemicarbazones and their copper complexes have been prepared and several single crystal structures examined. The copper complexes of these semicarbazone/thiosemicarbazones were prepared and several crystal structures examined. The single crystal X-ray structure of the pyridyl-substituted semicarbazone showed two types of copper complexes, a monomer and a dimer. We also found that the p-nitrophenyl semicarbazone formed a conventional ‘magic lantern’ acetate-bridged dimer. Electron Paramagnetic Resonance (EPR) of several of the copper complexes was consistent with the results of single crystal X-ray crystallography. The EPR spectra of the p-nitrophenyl semicarbazone copper complex in dimethylsulfoxide (DMSO) showed the presence of two species, confirming the structural information. Since thiosemicarbazones and semicarbazones have been reported to exhibit anticancer activity, we examined the anticancer activity of several of the derivatives reported in the present study and interestingly only the thiosemicarbazone showed activity while the semicarbazones were not active indicating that introduction of sulphur atom alters the biological profile of these thiosemicarbazones.

Green synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles at the platinum anode in acetic acid

The electroorganic synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles from the anodic oxidation of semicarbazone has been carried out at platinum anode in acetic acid under constant potential electrolysis in an undivided cell. This is an environmentally benign method in the field of synthetic organic chemistry. The products are characterized by IR, 1H and 13C NMR, and elemental analysis.

Synthesis, antimicrobial and insecticidal activity of some 4H-1, 2, 4 triazole derivatives

1-(Substituted benzylidene) semicarbazide has been used as a precursor to synthesize some important biologically active 3- substituted phenyl, 4H-1, 2, 4 triazole derivatives. Reaction of ethanolic solution of schiff s base of substituted aromatic aldehyde 1 with ethanolic solution of FeCl 3.6H2O (1 mole FeCl3.6H2O in 10 mL ethanol) yields the 4N-1, 2, 4 triazole-3-derivative 2. Several derivatives have been synthesized and screened for their antibacterial efficacy against Bacillus subtilis, Escherichia coli, Staphyllococcus aureus and Klebsiella pneumoniae, Antifungal activity against Aspergillus flavus, Fusarium oxysporum, Aspergillus niger and Trichoderma viridae and insecticidal activity against Periplaneta americana.

Effect of semicarbazones on endogenous protein hydrolysis in liver homogenate

Semicarbazones of substituted benzaldehydes were synthesized and their effect on endogenous protein hydrolysis in liver homogenate was studied. It was found that p-nitrobenzaldehyde semicarbazone exerted maximum effect.

Evaluation of semicarbazones for anticonvulsant and sedative-hypnotic properties

A series of semicarbazones and thiosemicarbazones were synthesized and evaluated for anti-convulsant activity. Some compounds provided significant protection against Maximal Electroshock (MES) and subcutaneous strychnine induced seizures. Compound 1 was the most active in the series with activity in a dose of 30 mg/kg in the strychnine seizure pattern test and an ED50 of 10 mg/kg in the MES test. Hence it could serve as a prototype molecule for future development. Also compounds with a p-nitrophenyl substitution in place of the amino hydrogen of semicarbazone moiety showed activity in a dose of 30 mg/kg and an ED50 of 83 mg/kg in the MES test.