84807-26-1

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Nitro-2,3-dihydro-1H-indole serves as a key intermediate in the pharmaceutical industry, utilized for the synthesis of various medicinal compounds. Its presence as a nitro-containing heterocyclic compound makes it a versatile component in the creation of new drugs with potential therapeutic applications.
Used in Organic Chemistry:
In the realm of organic chemistry, 4-Nitro-2,3-dihydro-1H-indole is employed as a valuable intermediate. The nitro group attached to the molecule allows it to participate in numerous chemical reactions, facilitating the production of a broad spectrum of different organic compounds for research and industrial applications.
Used in Chemical Research:
4-Nitro-2,3-dihydro-1H-indole is also used in chemical research settings to explore novel reactions and mechanisms involving nitro-containing heterocyclic systems. Its unique structure provides opportunities for scientists to investigate new pathways and develop innovative synthetic methodologies.
Safety Note:
It is crucial to handle 4-Nitro-2,3-dihydro-1H-indole with care due to its potential hazards. As with any chemical compound, proper management and safety precautions are essential to mitigate health risks and ensure safe laboratory practices.

Upstream product

• 77759-08-1 2-(2,6-dinitrophenyl)ethanol 
• 4769-97-5 4-nitro-1H-indoIe 
• 606-20-2 2,6-dinitrotoluene 
• 52536-99-9 1-(2-chloroethyl)-2,6-dinitrobenzene 

Downstream Products

• 4769-97-5 4-nitro-1H-indoIe 

Relevant academic research and scientific papers

Compound with indoline skeleton, and preparation method and medical application of compound

The invention discloses a compound with an indoline skeleton, and a preparation method and medical application of the compound. The compound containing the indoline skeleton provided by the inventioncan interfere with Keap1-Nrf2 interaction activate Nrf2

Design, Synthesis, and Structure-Activity Relationships of Indoline-Based Kelch-like ECH-Associated Protein 1-Nuclear Factor (Erythroid-Derived 2)-Like 2 (Keap1-Nrf2) Protein-Protein Interaction Inhibitors

The Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor erythroid 2-related factor 2)-ARE (antioxidant response element) pathway is the major defending mechanism against oxidative stresses, and directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has been an attractive strategy to target oxidative stress-related diseases, including cardiovascular diseases. Here, we describe the design, synthesis, and structure-activity relationships (SARs) of indoline-based compounds as potent Keap1-Nrf2 PPI inhibitors. Comprehensive SAR analysis and thermodynamics-guided optimization identified 19a as the most potent inhibitor in this series, with an IC50 of 22 nM in a competitive fluorescence polarization assay. Further evaluation indicated the proper drug-like properties of 19a. Compound 19a dose-dependently upregulated genes and protein level of Nrf2 as well as its downstream markers and showed protective effects against lipopolysaccharide-induced injury in both H9c2 cardiac cells and mouse models. Collectively, we reported here a novel indoline-based Keap1-Nrf2 PPI inhibitor as a potential cardioprotective agent.

Discovery of N-indanyl benzamides as potent RORγt inverse agonists

The retinoic acid receptor-related orphan receptor-gamma-t (RORγt) is a promising therapeutic target for treatment of Th17 cell-mediated autoimmune diseases. Based on a scaffold hopping/conformational restriction strategy, a series of N-indanyl benzamides as novel RORγt inverse agonists was discovered. Exploration of structure-activity relationship on the piperazine ring, benzoyl moiety and cyclopentyl moiety of N-indanyl benzamides 2a and 2d led to identification of potent RORγt inverse agonists. Compound 5c with (S)-enantiomer was found having an IC50 of 153.7 nM in Fluorescence Resonance Energy Transfer (FRET) assay, and an IC50 of 47.1 nM in mouse Th17 cell differentiation assay, which represents a promising starting point for developing potent small molecule RORγt inverse agonists. Binding modes of the two enantiomers 5c and 5d in RORγt ligand binding domain were also discussed.

Discovery of novel N -β- d -Xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes

A novel series of N-linked β-d-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) in a cell-based assay. Of these, the 4-chloro-3-(4-cyclopropylbenzyl) -1-(β-d-xylopyranosyl)-1H-indole 19m was found to be the most potent inhibitor, with an EC50 value similar to that of the natural SGLT2 inhibitor phlorizin. Further studies in Sprague-Dawley (SD) rats indicated that 19m significantly increased urine glucose excretion in a dose-dependent manner with oral administration. The antihyperglycemic effect of 19m was also observed in streptozotocin (STZ) induced diabetic SD rats. These results described here are a good starting point for further investigations into N-glycoside SGLT2 inhibitors.

Synthesis of 2'-deoxyribofuranosyl indole nucleosides related to the antibiotics SF-2140 and neosidomycin

The 2'-deoxyribofuranose analog of the naturally occurring antibiotics SF-2140 and neosidomycin were prepared by the direct glycosylation of the sodium salts of the appropriate indole derivatives, with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose. Thus, treatment of the sodium salt of 4-methoxy-1H-indol-3-ylacetonitrile with 5 provided the blocked nucleoside, 4-methoxy-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1 -indol-3-ylacetonitrile, which was treated with sodium methoxide to yield the SF-2140 analog, 4-methoxy-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetoni rile. The neosidomycin analog was prepared by treatment of the sodium salt of 1H-indol-3-ylacetonitrile with 5 to obtain the blocked intermediate 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1H-3-ylacet nitrile followed by sodium methoxide treatment to give 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetonitrile and finally conversion of the nitrile function of 7b to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetamide. In a similar manner, indole and several other substituted indoles including 1H-indole-4-carbonitrile, 4-nitro-1H-indole, 4-chloro-1H-indole-2-carboxamide and 4-chloro-1H-indole-2-carbonitrile were each glycosylated and deprotected to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-4-carbonitrile, 4-nitro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carboxami e and 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carbonitr le, respectively. The 2'-deoxyadenosine analog in the indole ring system was prepared for the first time by reduction of the nitro group of 11c using palladium on carbon thus providing 4-amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole (1,3,7-trideaza-2'-deoxyadenosine).