611-09-6

Basic information

• Product Name: 5-Nitroisatin
• Synonyms: 1H-Indole-2,3-dione,5-nitro-;5-nitro-1h-indole-3-dione;5-nitro-indole-3-dione;5-nitro-isati;Indole-2,3-dione, 5-nitro-;Isatin, 5-nitro-;2,3-dihydro-5-nitroindole-2,3-dione;Nitroisatin
• CAS NO: 611-09-6
• Molecular Formula: C₈H₄N₂O₄
• Molecular Weight: 192.13
• EINECS: 210-252-5
• Product Categories: Indane/Indanone and Derivatives;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 611-09-6.mol

Chemical Properties

• Melting Point: 251 °C (dec.)(lit.)
• Boiling Point: 328.09°C (rough estimate)
• Appearance: Orange-yellow to orange/Crystalline Powder
• Density: 1.5513 (rough estimate)
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.06±0.20(Predicted)
• BRN: 180223
• CAS DataBase Reference: 5-Nitroisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroisatin(611-09-6)
• EPA Substance Registry System: 5-Nitroisatin(611-09-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40-68-22
• Safety Statements: 7-22-36/37/39-45-36/37
• RIDADR: 2811
• WGK Germany: 3
• RTECS: NL7970000
• HazardClass: IRRITANT
• Hazardous Substances Data: 611-09-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitroisatin is used as a reactant for the preparation of potential antibacterial and antifungal agents, specifically targeting the synthesis of spiro[indole-thiazolidinones], which are considered a medicinally important scaffold.
Used in Antimicrobial Applications:
5-Nitroisatin is utilized as a reactant for the development of potential antimicrobial agents, including antimycobacterial, anticonvulsant, and anthelminthic agents, as well as anti-human immunodeficiency virus (HIV) agents.
Used in Enzyme Inhibition:
5-Nitroisatin is employed as a reactant in the synthesis of inhibitors of human transglutaminase 2, an enzyme involved in various cellular processes and implicated in certain diseases.
Used in Antitubercular Drug Development:
5-Nitroisatin serves as a reactant for the preparation of potential antitubercular agents, which are crucial in the fight against tuberculosis.
Used in Neurological Disorders:
5-Nitroisatin is used as a reactant in the synthesis of acetylcholinesterase inhibitors, which have potential applications in the treatment of neurological disorders such as Alzheimer's disease.

Preparation

Isatin 30 (14.7 g, 0.1 mol) was added to conc. H2SO4 (121 ml) ?cooled to 0 oC in an ice-salt bath. Fuming HNO3 (4.2 ml) was ?added to this, drop by drop, in such a way that temperature should ?not rise above 5 oC. The reaction mixture was allowed to stand for ?about 30 minutes and then poured over crushed ice (500 g). A yellow precipitate separated ?immediately. The 5-Nitroisatin was filtered and washed with water and air dried to a constant ?weight (15 g). ?Yield : 85%

InChI:InChI=1/C8H4N2O4/c11-7-5-3-4(10(13)14)1-2-6(5)9-8(7)12/h1-3H,(H,9,11,12)

Upstream product

• 113423-47-5 3,3-dibromo-5-nitro-indolin-2-one 
• 91-56-5 indole-2,3-dione 
• 17122-62-2 hydroxyimino-acetic acid-(4-nitro-anilide) 
• 302-17-0 chloral hydrate 
• 100-01-6 4-nitro-aniline 
• 6146-52-7 5-nitroindole 
• 79-37-8 oxalyl dichloride 
• 62-53-3 aniline 
• 125600-42-2 2-amino-5-nitrophenylacetylene 
• 20870-79-5 5-nitrooxindole 
• 908295-26-1 3-iodo-5-nitro-1H-indole 
• 16135-31-2 p-nitroformanilide 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Downstream Products

• 55764-56-2 2-Oxy-6-nitro-chinolin-4-carbonsaeure 
• 109068-69-1 2-(4-methyl-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 108237-12-3 2-(4-acetylamino-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 109540-22-9 6-amino-2-phenyl-quinoline-4-carboxylic acid 
• 835901-20-7 2,2'-diphenyl-[6,6']azoxyquinoline-4,4'-dicarboxylic acid 
• 109068-71-5 2-(4-methoxy-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 42816-53-5 5-Aminoisatin 
• 73271-58-6 1-morpholin-4-ylmethyl-5-nitro-3-p-tolylimino-1,3-dihydro-indol-2-one 
• 73271-59-7 3-(2-ethoxy-phenylimino)-1-morpholin-4-ylmethyl-5-nitro-1,3-dihydro-indol-2-one 
• 83393-63-9 3-(2-Furan-2-yl-2-oxo-ethyl)-3-hydroxy-5-nitro-1,3-dihydro-indol-2-one 
• 129222-32-8 7-amino-1,2,3,4-tetrahydro-3-oxoacridine-9-carboxylic acid ethylene ketal 
• 129222-31-7 7-<5-(2-hydroxyethyloxy)-2-hydroxy>phenylamino-1,2,3,4-tetrahydro-3-oxoacridine-9-carboxylic acid ethylene ketal 
• 94493-38-6 4-hydroxy-2,3'-(5-nitro-oxindolydine)-4-phenylbut-3-enoic lactone 
• 77603-42-0 8-nitroindolo[2,1-b]quinazoline-6,12-dione 

Relevant articles and documents

Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases

Abstract: A new series of 21 Schiff bases of spiro-isatin was synthesized, and their DPPH, CUPRAC and ABTS cation radical scavenging abilities were investigated for antioxidant activity. The results showed that all the synthesized compounds exhibited anti

Design, synthesis and biological evaluation of novel 1,5-disubstituted isatin derivatives as antitumor agents

Isatin (1H-indole-2,3-dione) was reported to possess anticancer activities through its effect on tumor proliferation, apoptosis, and metastasis in vitro and in vivo. Here, we described the synthesis of a novel series of 1,5-disubstituted isatin derivative

Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase

Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.

Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives

The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.

Novel isatin derivative nitration method

The invention belongs to the technical field of chemical pharmacy and fine chemical engineering preparation, and particularly discloses a novel isatin derivative nitration method. Trifluoroacetic acidis adopted to replace traditional sulfuric acid, so tha

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.

1-benzylisatin derivative as well as synthesis method and application thereof

The invention relates to a 1-benzylisatin derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituents. The invention discloses structures of the compounds, a synthesis method of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activityof histone deacetylase 6; and the compounds can be further developed into drugs for treating Alzheimer's disease.

Diketoindole compound containing urea structure as well as preparation method and application of diketoindole compound

The invention relates to a diketoindole compound containing a urea structure as well as a preparation method and application of the diketoindole compound. The compound has a structure shown as a formula I in the specification. The invention also relates t

2,3-diketone indole compound, preparation method and applications thereof

The invention discloses a 2,3-diketone indole compound, a preparation method and applications thereof, wherein the compound has a structure represented by the following general formula (I) or (II). The invention further relates to a pharmaceutical composi

Synthesis and evaluation of isatin derivatives as antifungal agents

Various types of isatin derivatives were synthesized by reacting isatin with different reagents viz substituted acetophenones, sodium nitrate, hydroxylamine hydrochloride and hydrazine hydrate. Characterization of the synthesized compounds was done by using various spectral techniques such as IR,1HNMR,13CNMR, elemental analysis and mass spectrometry. Synthesized compounds were further evaluated for their antifungal activity against Helminthosporium oryzae, Rhizoctonia solani and Fusarium moniliforme using poison food technique. 3-(2-Oxo-2-phenylethylidene) indolin-2-one showed significant mycelium inhibition against all tested rice fungi.