76397-72-3

Usage

Uses

3-(Cyanoacetyl)-2-methylindole is used as a chemical intermediate for the synthesis of various compounds in the pharmaceutical and chemical industries. Its unique structure may offer potential applications in the development of new drugs, agrochemicals, or other specialty chemicals.
Used in Pharmaceutical Industry:
3-(Cyanoacetyl)-2-methylindole is used as a building block for the creation of novel drug molecules, potentially contributing to the discovery of new therapeutic agents. Its indole and cyanoacetyl components may provide a foundation for the design of molecules with specific biological activities, such as binding to certain receptors or enzymes.
Used in Chemical Industry:
3-(Cyanoacetyl)-2-methylindole is used as a precursor in the synthesis of complex organic compounds, which may have applications in materials science, such as the development of new polymers or dyes. Its reactivity and structural features could be harnessed to create innovative products with unique properties.
Further research and studies are necessary to fully understand the properties and potential applications of 3-(Cyanoacetyl)-2-methylindole, as its current documentation is limited. This may involve exploring its chemical reactivity, stability, and interactions with other compounds, as well as assessing its safety and efficacy in various applications.

InChI:InChI=1/C12H10N2O/c1-8-12(11(15)6-7-13)9-4-2-3-5-10(9)14-8/h2-5,14H,6H2,1H3

Upstream product

• 38693-08-2 2-chloro-1-(2-methyl-1H-indol-3-yl)ethan-1-one 
• 151-50-8 potassium cyanide 
• 95-20-5 2-methyl-1H-indole 
• 7062-95-5 potassium 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 1026993-72-5 4-(4-chlorophenyl)-3-methyl-6-(2-methyl-1H-indol-3-yl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 
• 1292766-35-8 3-cyano-2-(2-methyl-1H-indol-3-yl)-4-(2-naphthyl)-6-(4-ethylphenyl)pyridine 
• 1297612-45-3 (5-amino-2-phenyl-2H-1,2,3-triazol-4-yl)(2-methyl-1H-indol-3-yl)methanone 
• 1297612-47-5 2-cyano-N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]acetamide 
• 1297612-49-7 (E)-2-cyano-3-(dimethylamino)-N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]acrylamide 
• 1297612-51-1 (E)-2-cyano-3-hydrazinyl-N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]acrylamide 
• 1297612-53-3 5-amino-N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]-1H-pyrazole-4-carboxamide 
• 1297612-55-5 7-(2-methyl-1H-indol-3-yl)-5-oxo-2-phenyl-4,5-dihydro-2H-1,2,3-triazolo[4,5-b]pyridine-6-carbonitrile 
• 1297612-58-8 N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]-7-phenyl pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1297612-62-4 (2E,4E)-2-cyano-N-[5-(2-methyl-1H-indole-3-carbonyl)-2-phenyl-2H-1,2,3-triazol-4-yl]-5-phenylpenta-2,4-dienamide 
• 1297612-44-2 3-(2-methyl-1H-indol-3-yl)-3-oxo-2-(phenylhydrazono)propanenitrile 
• 1279650-23-5 2-[3,5-diphenyl-1,3,4-thiadiazol-2(3H)-ylidene]-3-(2-methyl-1H-indol-3-yl)-3-oxopropionitrile 
• 1279650-25-7 3-(2-methyl-1H-indol-3-yl)-2-[3-(4-nitrophenyl)-5-(thiophen-2-yl)-1,3,4-thiadiazol-2(3H)-ylidene]-3-oxopropionitrile 
• 1279650-26-8 ethyl 5-[1-cyano-2-(2-methyl-1H-indol-3-yl)-2-oxoethylidene]-4-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate 

Relevant academic research and scientific papers

Discovery of novel 4-azaaryl-N-phenylpyrimidin-2-amine derivatives as potent and selective FLT3 inhibitors for acute myeloid leukaemia with FLT3 mutations

Feline McDonough sarcoma (FMS)-like tyrosine kinase 3 (FLT3) is one of the most pursued targets in the treatment of acute myeloid leukaemia (AML) as its gene amplification and mutations, particularly internal tandem duplication (ITD), contribute to the pa

Novel uric acid-based nano organocatalyst with phosphorous acid tags: Application for synthesis of new biologically-interest pyridines with indole moieties via a cooperative vinylogous anomeric based oxidation

In this study, we have designed, synthesized and full characterized a novel biological based acidic nano organocatalyst via condensations reaction of uric acid and phosphorous acid. The obtained compound was named theacrine tetrakis(phosphonic acid) (TTPA) and prepared under refluxing ethanol. This new nano organocatalyst was applied as an efficient and recyclable catalyst for the preparation of novel pyridines with indole moieties via a cooperative vinylogous anomeric based oxidation with good to excellent yields.

Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents

A series of novel α-cyano substituted indolyl bis-chalcones (3a-l) has been synthesized and evaluated for their in vitro antitumor activity against the human breast cancer MCF7 (estrogen receptor-positive) and normal Vero cell lines using sulforhodamine B (SRB) assay method. Compounds 3a, 3c and 3d showed potent activity (GI50 = 11.7, 15.3 and 17.9 μM respectively) against the human breast cancer MCF7 cell line, which was almost as good as that of adriamycin (GI50 = 0.1 μM) whereas, screening against the normal Vero Monkey cell line showed moderate selectivity. Furthermore, all the synthesized compounds screened for their antioxidant potential against DPPH, NO, SOR, and H2O2 radicals. Most of the bis-chalcones exhibited significant DPPH (51.09-12.72 %) and NO (64.11-34.43 %) radical scavenging activity and modest activity against SOR (88.08-43.14 %) and H2O2 (80.13-56.0 %) radicals compared to the reference standard ascorbic acid (40.78 %, 42.63 %, 87.05 %, and 79.42 % respectively). Current study provides impetus for the development of highly potent indolyl bis-chalcone derivatives as anticancer leads.

Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents

In the present investigation, synthesis of a series of extended conjugated δ-chloro-α-cyano substituted indolyl chalcones (5a–p) was accomplished by reacting 3-cyanoacetylindole 2 with 3-chloro-3-phenyl-propenal 4 in the presence of piperidine. The struct

Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles

The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles 3. Further reaction with aminoguanidine yielded 5'-cyanomeridianin analogues 4. The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative 8. Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 3a with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4- yl)-(1H-indol-3-yl)-methanone 5 and the acrylic acid derivative 6 after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies. ARKAT-USA, Inc.

Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

Note on the Cyanoacetylation of Pyrroles and Indoles

Cyanoacetylation of pyrroles and indoles can be achieved by treatment with potassium cyanoacetate and methanesulfonyl chloride in acetonitrile with yields of 80-90percent.