5906-99-0

Basic information

• Product Name: 2-Nitrobenzenesulfonic acid hydrazide
• Synonyms: 2-Nitrobenzenesulfonic acid hydrazide;2-Nitrobenzenesulfonohydrazide;o-Nitrobenzenesulfonylhydrazide
• CAS NO: 5906-99-0
• Molecular Formula: C₆H₇N₃O₄S
• Molecular Weight: 217.2
• Mol File: 5906-99-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 101 °C (decomp)
• Boiling Point: 432.3±47.0 °C(Predicted)
• Appearance: /
• Density: 1.562±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly)
• PKA: 8.47±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Nitrobenzenesulfonic acid hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrobenzenesulfonic acid hydrazide(5906-99-0)
• EPA Substance Registry System: 2-Nitrobenzenesulfonic acid hydrazide(5906-99-0)

Safety Data

• Hazardous Substances Data: 5906-99-0(Hazardous Substances Data)

Usage

General Description

2-Nitrobenzenesulfonic acid hydrazide is a chemical compound with the molecular formula C6H7N3O6S. It is a hydrazide derivative of 2-nitrobenzenesulfonic acid and is commonly used as a reagent in organic synthesis. 2-Nitrobenzenesulfonic acid hydrazide is a white to light yellow crystalline powder that is soluble in water. It is used in the production of azo dyes and as a reagent for the determination of traces of aluminum. 2-Nitrobenzenesulfonic acid hydrazide is also known for its anti-tumor and anti-fibrotic activities, and it has been studied for its potential therapeutic applications in these areas.

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 

Downstream Products

• 6655-36-3 2-nitro-benzenesulfonic acid cyclohexylidenehydrazide 
• 83451-27-8 1-(2-Nitrobenzenesulfonyl)-4-carbethoxy-5-aminopyrazole 
• 17538-94-2 endo-6-phenylbenzobicyclo<3.1.0>hex-2-ene 
• 13658-73-6 3,5-dimethyl-1-((2-nitrophenyl)sulfonyl)-1H-pyrazole 
• 86-00-0 2-nitrobiphenyl 
• 577-59-3 2-acetylnitrobenzene 

Relevant articles and documents

Synthesis of alkaloid (-)-205b via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition

An asymmetric synthesis of alkaloid (-)-205B, a tricyclic member of the architecturally diverse family of natural products isolated from the skin of neotropical poison frogs, is described that proceeds through two recently developed stereoselective synthetic methods: (1) Ti-mediated allylic alcohol-imine reductive cross-coupling and (2) intramolecular [3+2] cycloaddition of a glyoxylate-based homoallylic nitrone. The utility of this latter cycloaddition process for the assembly of the stereochemically dense piperidine core of 205B is noteworthy, as this method enables direct [3+2] cycloaddition of an intermediate homoallylic (E)-nitrone via a pathway that is stereochemically unscathed by competitive [3,3]-sigmatropic rearrangement processes. Overall, the synthesis is asymmetric, concise, and highly stereoselective-features which point to the potential future utility of these chemical methods in natural product synthesis and medicinal chemistry.

Synthesis of benzimidazole derivatives as potent inhibitors for α-amylase and their molecular docking study in management of type-II diabetes

In the search of potent α-amylase inhibitors, we have synthesized seventeen derivatives of 2-mercaptobenzimidazole bearing sulfonamide (1–17) and evaluated for their α-amylase inhibitory potential. All synthesized compounds display a variable degree of α-amylase activity having IC50 values ranging between 0.90 ± 0.05 to 11.20 ± 0.30 μM when compared with the standard drug acarbose having IC50 value 1.70 ± 0.10 μM. Compound 1, 2, 11, 12 and 14 having IC50 values 1.40 ± 0.10, 1.30 ± 0.05, 0.90 ± 0.05, 1.60 ± 0.05 and 1.60 ± 0.10 μM respectively were found many folds better than the standard drug acarbose. While others derivatives of the series showed good inhibitory potentials. All the synthesized compounds were characterized by HREI-MS, 1H and 13C NMR spectroscopy. Structure activity relationship (SAR) has been established for all newly synthesized analogs. Binding interactions between ligands and active residues of the enzyme were confirmed through molecular docking study.

Synthesis, in vitro α-amylase inhibitory, and radicals (DPPH & ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles

Over-expression of α-amylase enzyme causes hyperglycemia which lead to many physiological complications including oxidative stress, one of the most commonly associated problem with diabetes mellitus. Marketed α-amylase inhibitors such as acarbose, voglibose, and miglitol used to treat type-II diabetes mellitus, but also linked to several harmful effects. Therefore, it is essential to explore new and nontoxic antidiabetic agents with additional antioxidant properties. In this connection, a series of new N-sulfonohydrazide substituted indazoles 1–19 were synthesized by multistep reaction scheme and assessed for in vitro α-amylase inhibitory and radical (DPPH and ABTS) scavenging properties. All compounds were fully characterized by different spectroscopic techniques including 1H, 13C NMR, EI-MS, HREI-MS, ESI-MS, and HRESI-MS. Compounds showed promising α-amylase inhibitory activities (IC50 = 1.23 ± 0.06–4.5 ± 0.03 μM) as compared to the standard acarbose (IC50 1.20 ± 0.09 μM). In addition to that all derivatives were found good to moderate scavengers of DPPH (IC50 2.01 ± 0.13–5.3 ± 0.11) and ABTS (IC50 = 2.34 ± 0.07–5.5 ± 0.07 μM) radicals, in comparison with standard ascorbic acid having scavenging activities with IC50 = 1.99 ± 0.09 μM, and IC50 2.03 ± 0.11 μM for DPPH and ABTS radicals. In silico molecular docking study was conducted to rationalize the binding interaction of α-amylase enzyme with ligands. Compounds were observed as mixed type inhibitors in enzyme kinetic characterization.