4071-16-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-methyl-1H-indol-3-yl)acetonitrile is used as a building block for the synthesis of various bioactive compounds. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals with diverse therapeutic applications.
Used in Medicinal Chemistry Research and Development:
As a compound of interest, 2-(2-methyl-1H-indol-3-yl)acetonitrile is utilized in medicinal chemistry for further research and development. Its structural diversity and potential pharmacological activities contribute to the exploration of new therapeutic agents and drug candidates.
Used as a Synthetic Intermediate:
2-(2-methyl-1H-indol-3-yl)acetonitrile is used as a versatile synthetic intermediate, capable of undergoing various chemical reactions. This allows for the production of a wide range of functionalized indole derivatives, which can be further utilized in the synthesis of complex organic compounds and pharmaceuticals.

InChI:InChI=1/C11H10N2/c1-8-9(6-7-12)10-4-2-3-5-11(10)13-8/h2-5,13H,6H2,1H3

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 37125-92-1 2-methylgramine 
• 77-78-1 dimethyl sulfate 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 65881-18-7 1-Acetyl-2-methyl-3-oxo-2,3-dihydroindole 
• 2274-50-2 phenylalanine-o-carboxylic acid 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 590-17-0 cyanomethyl bromide 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 

Downstream Products

• 2731-06-8 2-methyltryptamine 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 16979-83-2 benzylidene-[2-(2-methyl-indol-3-yl)-ethyl]-amine 
• 88110-03-6 (3aS,6aS,11bR)-3a-Methyl-4,6-bis-[1-phenyl-meth-(Z)-ylidene]-3a,4,6a,7-tetrahydro-3H,6H-pyrrolo[2,3-d]carbazole-2,5-dione 
• 88110-04-7 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-6-Cinnamyliden-3a,6,6a,7-Tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 
• 88110-06-9 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-7-Benzoyl-3a,6,6a,7-tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 
• 88110-07-0 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-6-Benzyliden-3a,6,6a,7-Tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 

Relevant academic research and scientific papers

Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile

The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.