62368-07-4

Usage

Uses

Used in Advanced Organic Chemical Synthesis:
1-Acetyl-5-bromo-7-nitroindoline is used as a key intermediate for the synthesis of various complex organic molecules. Its unique reactivity and versatility make it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals. The presence of the acetyl, bromine, and nitro groups allows for a wide range of chemical reactions, facilitating the formation of diverse molecular structures.
Used in Pharmaceutical Development:
1-Acetyl-5-bromo-7-nitroindoline is used as a building block in the development of new pharmaceutical compounds. Its structural features enable the creation of potential drug candidates with novel mechanisms of action, potentially leading to the discovery of new treatments for various diseases and conditions. 1-Acetyl-5-bromo-7-nitroindoline's reactivity also allows for the exploration of its potential as a prodrug, which could be converted into an active therapeutic agent within the body.
Used in Research and Development:
1-Acetyl-5-bromo-7-nitroindoline is used as a research tool in academic and industrial laboratories. Its unique properties make it an interesting subject for studies in organic chemistry, chemical synthesis, and materials science. Researchers may use 1-Acetyl-5-bromo-7-nitroindoline to investigate new reaction pathways, explore the effects of structural modifications on reactivity, or develop new synthetic strategies for the preparation of complex molecules.
Used in Specialty Chemical Production:
1-Acetyl-5-bromo-7-nitroindoline is used as a raw material in the production of specialty chemicals, such as dyes, pigments, and other performance chemicals. Its unique structural features can contribute to the development of new products with improved properties, such as enhanced color, stability, or reactivity. 1-Acetyl-5-bromo-7-nitroindoline's versatility in chemical reactions also allows for the creation of a wide range of specialty chemicals with diverse applications.

InChI:InChI=1/C10H9BrN2O3/c1-6(14)12-3-2-7-4-8(11)5-9(10(7)12)13(15)16/h4-5H,2-3H2,1H3

Upstream product

• 22190-38-1 5-bromo-N-acetylindoline 
• 496-15-1 1-indoline 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 22190-33-6 5-bromoindoline 

Downstream Products

• 80166-90-1 5-Bromo-7-nitroindoline 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 133433-62-2 1-(7-amino-5-bromoindolin-1-yl)ethan-1-one 
• 165669-16-9 5-Bromo-7-nitroindole 

Relevant academic research and scientific papers

The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions with G-Quadruplex DNA

G-quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure–activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

Using weak interactions to control C-H mono-nitration of indolines

An unprecedented C-H mononitration of indolines either at the -C5 or -C7 positions under mild condition is reported here. The roles of multiple weak interactions and factors such as steric factors, electronic effects, cation-π interactions, and solvent polarity were established, and we achieved a 100% regioselective electrophilic aromatic (EArS) nitration using Cu(NO3)2 or AgNO3.

A rapid and clean synthetic approach to cyclic peptides: Via micro-flow peptide chain elongation and photochemical cyclization: Synthesis of a cyclic RGD peptide

A cyclic RGD peptide was efficiently synthesized based on micro-flow, triphosgene-mediated peptide chain elongation and micro-flow photochemical macrolactamization. Our approach enabled a rapid (amidation for peptide chain elongation 5 s, macrolactamization 5 min) and clean (only one column chromatographic separation) synthesis of a cyclic peptide.

Light-sensitive protecting groups for amines and alcohols: The photosolvolysis of n-substituted 7-nitroindolines

Representative examples of primary and secondary amines were protected as urea derivatives 4 of 5-bromo-7-nitroindoline and even more efficiently as ureas 8 derived from 5,7-dinitroindoline, via high-yield reactions with carbamoyl chlorides 3 and 7, respectively. Deprotection of 4 or 8 was achieved in high yields by UV irradiation at room temperature in Pyrex vessels under neutral conditions and exclusion of air. In a similar manner the dinitroindolines serve as protecting groups for alcohols and phenols; the derived carbamates 5 and 9 can likewise be deprotected photochemically in high yields. Georg Thieme Verlag Stuttgart.

Bioavailable acyl-CoA : Cholesterol acyltransferase inhibitor with anti- peroxidative activity: Synthesis and biological activity of novel indolinyl amide and urea derivatives

We synthesized a series of indoline derivatives with an amide or urea moiety and examined their inhibitory effects on acyl-CoA : cholesterol acyltransferase (ACAT) activity, lipid-peroxidation and serum cholesterol levels in experimental animals. Among the derivatives synthesized, a series of N-(1-alkyl-4,6- dimethylindolin-7-yl)-2,2-dimethylpropanamides potently inhibited rabbit intestinal ACAT activity and lipid-peroxidation of rat brain homogenate. The effect on ACAT activity was related to the length of the alkyl chain at the 1-position of indoline. N-(4,b-Dimethyl-1-octylindolin-7- yl)-2,2-dimethylpropanamide hydrochloride (55) showed inhibitory effects on intestinal and hepatic ACAT activity slightly weaker than those of YM-750, and an inhibitory effect on low density lipoprotein (LDL)-peroxidation similar to that of probucol. Compound 55 also reduced serum cholesterol at 10 mg/kg/d in hyperlipidemic rats and 20 mg/kg/d in normolipidemic hamsters. The plasma concentration of 55 reached 716 ng/ml in dogs (10 mg/kg, p.o.), which is an effective concentration against hepatic ACAT activity and LDL- peroxidation. In conclusion, compound 55 is a novel bioavailable ACAT inhibitor with anti-peroxidative activity and is thus a promising anti- atherosclerotic and anti-hyperlipidemic drug. Indoline proved to be a useful pharmacophore for molecular design of new anti-peroxidative drugs.