32692-19-6

Basic information

• Product Name: 5-Nitroindoline
• Synonyms: 2,3-DIHYDRO-5-NITRO-(1H)-INDOLE;2,3-DIHYDRO-5-NITROINDOLE;AKOS BC-0893;5-NITRO-2,3-DIHYDRO-1H-INDOLE;5-NITROINDOLINE;2,3-dihydro-5-nitro-1h-indol;5-nitro-indolin;5-Nitro-2,3-Dihydroindole
• CAS NO: 32692-19-6
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• EINECS: 251-158-4
• Product Categories: Indoles and derivatives;Indoline & Oxindole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 32692-19-6.mol

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 324.4 °C at 760 mmHg
• Flash Point: 150 °C
• Appearance: /
• Density: 1.298 g/cm³
• Vapor Pressure: 0.000246mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 0.86±0.20(Predicted)
• CAS DataBase Reference: 5-Nitroindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroindoline(32692-19-6)
• EPA Substance Registry System: 5-Nitroindoline(32692-19-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: NM1930000
• HazardClass: IRRITANT
• Hazardous Substances Data: 32692-19-6(Hazardous Substances Data)

Usage

Uses

5-Nitroindoline was used to prepare acetylated glucosylamines using the Suvorov procedure.

InChI:InChI=1/C8H8N2O2/c11-10(12)7-1-2-8-6(5-7)3-4-9-8/h1-2,5,9H,3-4H2

Upstream product

• 496-15-1 1-indoline 
• 108-24-7 acetic anhydride 
• 33632-27-8 1-(5-nitro-2,3-dihydroindol-1-yl)ethanone 
• 108619-08-5 (5-nitroindoline-1-yl)(phenyl)methanone 
• 6146-52-7 5-nitroindole 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 6037-73-6 1-benzyl-2,3-dihydro-1H-indole 
• 64-17-5 ethanol 
• 100-01-6 4-nitro-aniline 
• 120-72-9 indole 
• 20870-79-5 5-nitrooxindole 

Downstream Products

• 15918-80-6 5-amino indoline 
• 87240-06-0 7-bromo-5-nitroindoline 
• 6146-52-7 5-nitroindole 
• 136633-52-8 1-N-methoxycarbonylsulfanilyl-5-nitroindoline 
• 18711-25-6 1-Methyl-5-nitroindoline 
• 1026940-90-8 {(E)-(S)-4-(5-Nitro-2,3-dihydro-indol-1-yl)-4-oxo-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enyl}-carbamic acid tert-butyl ester 
• 87866-11-3 2-chloro-1-(5-nitroindolin-1-yl)ethanone 
• 227956-83-4 1-benzyl-5-nitro-2,3-dihydro-1H-indole 
• 4993-96-8 1-(5-aminoindolin-1-yl)ethanone 
• 29742-55-0 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-nitroindole 
• 727651-35-6 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-nitroindole 
• 727651-37-8 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-nitroindoline-2,3-dione 
• 21909-45-5 1-benzyl-2,3-dihydro-1H-indol-5-ylamine 
• 848133-83-5 6-amino-4-(1-benzyl-2,3-dihydro-1H-indol-5-ylamino)-7-ethoxyquinoline-3-carbonitrile 

Relevant articles and documents

Increased antibacterial properties of indoline-derived phenolic Mannich bases

The search for antibacterial agents for the combat of nosocomial infections is a timely problem, as antibiotic-resistant bacteria continue to thrive. The effect of indoline substituents on the antibacterial properties of aminoalkylphenols was studied, leading to the development of a library of compounds with minimum inhibitory concentrations (MICs) as low as 1.18 μM. Two novel aminoalkylphenols were identified as particularly promising, after MIC and minimum bactericidal concentrations (MBC) determination against a panel of reference strain Gram-positive bacteria, and further confirmed against 40 clinical isolates (Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Enterococcus faecium, and Listeria monocytogenes). The same two aminoalkylphenols displayed low toxicity against two in vivo models (Artemia salina brine shrimp and Saccharomyces cerevisiae). The in vitro cytotoxicity evaluation (on human keratinocytes and human embryonic lung fibroblast cell lines) of the same compounds was also carried out. They demonstrated a particularly toxic effect on the fibroblast cell lines, with IC50 in the 1.7–5.1 μM range, thus narrowing their clinical use. The desired increase in the antibacterial properties of the aminoalkylphenols, particularly indoline-derived phenolic Mannich bases, was reached by introducing an additional nitro group in the indolinyl substituent or by the replacement of a methyl by a bioisosteric trifluoromethyl substituent in the benzyl group introduced through use of boronic acids in the Petasis borono-Mannich reaction. Notably, the introduction of an additional nitro moiety did not confer added toxicity to the aminoalkylphenols.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

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.

Rh(III)-Catalyzed C7-Thiolation and Selenation of Indolines

The rhodium(III)-catalyzed intermolecular C7-thiolation and selenation of indolines with disulfides and diselenides were developed. This protocol relies on the use of a removable pyrimidyl directing group to access valuable C-7 functionalized indoline scaffolds with ample substrate scope and broad functional group tolerance.

Iron-catalysed sequential reaction towards α-aminonitriles from secondary amines, primary alcohols and trimethylsilyl cyanide

We have developed a one-pot iron-catalysed sequential reaction of secondary amines with primary alcohols, trimethylsilyl cyanide and TBHP under mild reaction conditions to give the corresponding α-aminonitriles.

NOVEL PROTEIN TYROSINE PHOSPHATASE - IB INHIBITORS

The present invention relates to the novel compounds of the general formula (I), wherein the symbols are same as described in specification, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, to process and intermediates for the preparation of the above said compounds, having the utility of these compounds in medicine and to methods for their therapeutic use, and their use in the treatment of metabolic disorders.

QUINOLONE AND TETRAHYDROQUINOLONE AND RELATED COMPOUNDS HAVING NOS INHIBITORY ACTIVITY

The present invention features quinolones, tetrahydroquinolines, and related compounds that inhibit nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing various medical conditions.

Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 1: Identification and structure-activity relationships

Optimization of the lead compound 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2,3-dihydro-indol-1-yl)-ethanone 1 by systematic structure-activity relation (SAR) studies lead to two potent compounds 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)- ethanone 2n and 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)- ethanone 7b. Their related synthesis was also reported.

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.