4414-79-3

Usage

Uses

Used in Pharmaceutical Synthesis:
1H-indole-1-propiononitrile is used as a key intermediate in the synthesis of various pharmaceutical products for its ability to form a variety of different derivatives, contributing to the development of new medications.
Used in Agrochemical Production:
1H-indole-1-propiononitrile is used as a building block in the production of agrochemicals, playing a crucial role in the creation of effective compounds for agricultural applications.
Used in Organic Synthesis:
1H-indole-1-propiononitrile is used as a versatile reactant in organic synthesis for its capacity to react with other chemicals, enabling the formation of a wide range of chemical derivatives.
Used in Biological Research:
1H-indole-1-propiononitrile is used as a subject of study in biological research for its potential antimicrobial and anticancer properties, aiding in the discovery of new therapeutic agents.

InChI:InChI=1/C11H10N2/c12-7-3-8-13-9-6-10-4-1-2-5-11(10)13/h1-2,4-6,9H,3,8H2

Upstream product

• 120-72-9 indole 
• 107-13-1 acrylonitrile 
• 2417-90-5 bromopropionitrile 
• 71-43-2 benzene 

Downstream Products

• 46170-17-6 3-(1H-indol-1-yl)propan-1-amine 
• 20892-46-0 3-(1H-indol-1-yl)-N,N-dimethylaminopropan-1-amine 
• 6639-06-1 3-indol-1-yl-propionic acid 
• 61123-70-4 3-(2,3-dihydro-1H-indole-1-yl)propan-1-amine 
• 91349-96-1 3-(indolin-1-yl)propanenitrile 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Derivatives of Indoline as Highly Potent Antioxidant and Anti-inflammatory Agents

We describe the preparation and evaluation of novel indoline derivatives with potent antioxidant and anti-inflammatory activities for the treatment of pathological conditions associated with chronic inflammation. The indolines are substituted at position 1 with chains carrying amino, ester, amide, or alcohol groups, and some have additional substituents, Cl, MeO, Me, F, HO, or BnO, on the benzo ring. Concentrations of 1 pM to 1 nM of several compounds protected RAW264.7 macrophages against H2O2 induced cytotoxicity and LPS induced elevation of NO, TNF-α, and IL-6. Several derivatives had anti-inflammatory activity at 1/100th of the concentration of unsubstituted indoline. Four compounds with ester, amine, amide, or alcohol side chains injected subcutaneously in mice at a dose of 1 μmol/kg or less, like dexamethasone (5.6 μmol/kg) prevented LPS-induced cytokine elevation in the brain and peripheral tissues. Subcutaneous injection of 100 μmol/kg of these compounds caused no noticeable adverse effects in mice during 3 days of observation.

Olefin-Oriented Selective Synthesis of Linear and Branched N-Alkylated Heterocycles by Hydroamination

An effective base-induced selective approach for the synthesis of linear and branched N-alkylated heterocycles by hydroamination of olefins has been described. The designed C–N bond formation method was directed through the olefin, as with styrenes only linear N-alkylated product was obtained, and acrylates gave linear as well as branched alkylated heterocycles. This protocol provided the synthesis of exclusive N-alkylated product instead of the C-3 Michael addition product. The reaction was also compatible with phenyl vinyl sulfone, thus leading to the formation of sulfone substituted heterocycles in good yield. Further, the method was utilized for the synthesis of medicinally important analogs of CB1 Cannabinoid receptor and Dimebon analogue in short reaction sequence.

KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions

Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.

Efficient protocol for Aza-Michael addition of N-heterocycles to α,β-unsaturated compound using [Ch]OH and [n-butyl urotropinium]OH as basic ionic liquids in aqueous/solvent free conditions

The present work emphasizes on a green methodology using designed and synthesized basic ionic liquid, [n-butyl Urotropinium]OH, and commercially available aqueous solution of choline hydroxide [Ch]OH as catalysts for executing Aza-Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature. The highlighting features of these catalysts include using low concentration of both catalysts along with [Ch]OH being low cost and biodegradable, [n-butyl Urotropinium]OH significantly enhancing the high substrate/catalyst ratio to obtain the desired products in high yield and purity in most cases. Further, both catalysts were recyclable and recoverable up to five cycles.

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Signal transducer and activator of transcription 3 (STAT3) is constitutively activated in malignant tumors and plays important roles in multiple aspects of cancer aggressiveness. Thus, targeting STAT3 promises to be an attractive strategy for the treatment of advanced metastatic tumors. Bisindolylmaleimide alkaloid (BMA) has been shown to have anti-cancer activities and was thought to suppress tumor cell growth by inhibiting protein kinase C. In this study, we show that a newly synthesized BMA analog, BMA097, is effective in suppressing tumor cell and xenograft growth and in inducing spontaneous apoptosis. We also provide evidence that BMA097 binds directly to the SH2 domain of STAT3 and inhibits STAT3 phosphorylation and activation, leading to reduced expression of STAT3 downstream target genes. Structure activity relationship analysis revealed that the hydroxymethyl group in the 2,5-dihydropyrrole-2,5-dione prohibits STAT3 inhibitory activity of BMA analogs. Altogether, we conclude that the synthetic BMA analogs may be developed as anti-cancer drugs by targeting and binding to the SH2 domain of STAT3 and inhibiting the STAT3 signaling pathway.

INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF

The present invention is directed to indoline derivatives and salts thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders associated with at least one of oxidative stress, an immune response, release of NO and release of pro-inflammatory cytokine.

Bisindolyl maleimide derivative and preparation method and application thereof

The invention provides a bisindolyl maleimide derivative and a preparation method and application thereof. The bisindolyl maleimide derivative has an excellent alpha-glucosidase inhibition effect and can be used for preventing and treating diabetes.

Bisindolylmaleimide derivative, and preparation method and use thereof

The invention provides a bisindolylmaleimide derivative, and a preparation method and a use thereof. The bisindolylmaleimide derivative has a good tumor treatment effect, especially has a good treatment effect on some drug-resistant tumors, and can realize accurate treatment of the drug-resistant tumors.

Selective N-alkylation of indoles with α,β-unsaturated compounds catalyzed by a monomeric phosphate

Catalytic N-alkylation of indoles is challenging because the N1 nitrogen atoms are inert toward electrophilic reagents. Herein, an organic-solvent- soluble alkylammonium salt of a simple monomeric phosphate ion, [PO 4]3-, with a high charge density acts as an efficient homogeneous catalyst for selective N-alkylation of indoles with α,β-unsaturated compounds. For the reaction of indole with ethyl acrylate, the turnover number reached up to 36 and the turnover frequency was 216 h-1; these values are the highest among those reported for base-mediated systems so far. In the presence of [PO4]3- ions, various combinations of nitrogen nucleophiles (ten examples) and α,β-unsaturated compounds (four examples) were efficiently converted to the desired N-alkylated products in high yields. NMR and IR spectroscopies showed formation of the indolyl anion through the activation of indole by the [PO4]3- ion, which plays an important role in the present N-alkylation.

Pd-catalyzed direct coupling of indoles with carbon monoxide and alkynes: Selective synthesis of linear α,β-unsaturated ketones

A new strategy is described for the direct coupling of indoles with CO and alkynes to generate α,β-unsaturated ketones. This procedure, employing Xantphos and Pd(CH3CN)4(BF4) 2, is attractive from both environmental and operational points of view and adds value to the method for the carbonylation of alkynes by using carbon nucleophiles and affording linear regioselectivity.