20356-45-0

Usage

Uses

Used in Organic Synthesis:
3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE is used as a synthetic building block for the creation of various organic compounds. Its application in organic synthesis is due to its ability to undergo a range of chemical reactions, such as nucleophilic addition, electrophilic substitution, and cyclization, which can lead to the formation of a diverse array of molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE is used as a key intermediate in the synthesis of indole-based drugs. These drugs have potential applications in the treatment of various medical conditions, such as inflammation, pain, and certain types of cancer. The compound's reactivity and structural diversity make it a valuable asset in the development of new therapeutic agents.
Used in Chemical Research:
3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE is also utilized in chemical research as a model compound for studying the properties and reactivity of indole-containing molecules. This research can provide valuable insights into the design and synthesis of new indole-based compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemistry.

InChI:InChI=1/C11H8N2O/c12-6-5-11(14)9-7-13-10-4-2-1-3-8(9)10/h1-4,7,13H,5H2

Upstream product

• 120-72-9 indole 
• 7062-95-5 potassium 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 28755-03-5 3-chloroacetylindole 
• 151-50-8 potassium cyanide 

Downstream Products

• 85452-78-4 (E)-3-(1H-indol-3-yl)acrylonitrile 
• 937209-06-8 3-(1H-indol-3-yl)-2-(mercapto(phenylamino)methylene)-3-oxopropanenitrile 
• 1020091-74-0 C₂₉H₁₆BrN₅ 
• 1020091-75-1 C₃₀H₁₉N₅ 
• 1020091-71-7 4-(4-chlorophenyl)-2,6-di(1H-indol-3-yl)pyridine-3,5-dicarbonitrile 
• 1020091-73-9 4-(2-chlorophenyl)-2,6-di(1H-indol-3-yl)pyridine-3,5-dicarbonitrile 
• 1020091-77-3 C₂₉H₁₆N₆O₂ 

Relevant academic research and scientific papers

Ketene dithioacetal mediated synthesis of 1,3,4,5-tetrasubstituted pyrazole derivatives and their biological evaluation

Ketene dithioacetal mediated chemo- and regioselective synthesis of a series of novel 1,3,4,5-tetrasubstituted pyrazole derivatives (4a-l) integrated with a bioactive indole nucleus was achieved by reacting substituted 2-(1-methyl-1H-indole-3-carbonyl)-3,

Synthesis, molecular docking, and biofilm formation inhibitory activity of bis(Indolyl)pyridines analogues of the marine alkaloid nortopsentin

An efficient and simple protocol for the synthesis of a new class of diverse bis(indolyl)pyridines analogues of the marine alkaloid nortopsentin has been reported. A one-pot four-component condensation of 3-cyanocarbomethylindole, various aldehyde, 3-acetylindole, and ammonium acetate in glacial acetic acid led to the formation of 2,6-bis(1H-indol-3-yl)-4-(substituted-phenyl)pyridine-5-carbonitriles. Additionally, 2,6-bis(1H-indol-3-yl)-4-(benzofuran) pyridine-5-carbonitriles were prepared via a one-pot four-component condensation of 3-cyanocarbomethylindole, various N-substituted-indole-3-aldehydes, 2-acetylbenzofuran, and ammonium acetate. The synthesized compounds were evaluated for their ability to inhibit biofilm formation against the Gram-positive bacterial reference strains Staphylococcus aureus ATCC 6538 and the Gram-negative strain Escherichia coli ATCC 25922. Some of the new compounds showed a marked selectivity against the Gram-positive and Gram-negative strains. Remarkably, five compounds 4b, 7a, 7c, 7d and 8e demonstrated good antibiofilm formation against S. aureus and E. coli. On the other hand, the release of reducing sugars and proteins from the treated bacterial strains over the untreated strains was considered to explain the disruption effect of the selected compound on the contact cells of S. aureus and E. coli. Out of all studied compounds, the binding energies and binding mode of bis-indole derivatives 7c and 7d were theoretically the best thymidylate kinase, DNA gyrase B and DNA topoisomerase IV subunit B inhibitors.

Antileishmanial Activity of Pyrazolopyridine Derivatives and Their Potential as an Adjunct Therapy with Miltefosine

A series of pyrazolo(dihydro)pyridines was synthesized and evaluated for antileishmanial efficacy against experimental visceral leishmaniasis (VL). Among all compounds, 6d and 6j exhibited better activity than miltefosine against intracellular amastigotes. Compound 6j (50 mg/kg/day) was further studied against Leishmania donovani/BALB/c mice via the intraperitoneal route for 5 days and displayed >91 and >93% clearance of splenic and liver parasitic burden, respectively. Combination treatment of 6j with a subcurative dose of miltefosine (5 mg/kg) in BALB/c mice almost completely ameliorated the disease (>97% inhibition) by augmenting nitric oxide generation and shifting the immune response toward Th1. Furthermore, investigating the effect of 6j on Leishmania promastigotes revealed that it induced molecular events, such as a loss in mitochondrial membrane potential, externalization of phosphatidylserine, and DNA fragmentation, that ultimately resulted in the programmed cell death of the parasite. These results along with pharmacokinetic studies suggest that 6j could be a promising lead for treating VL as an adjunct therapy with miltefosine.

Studies with enamines and azaenamines: Synthesis and reactivity of 3-dimethylamino-2-[(3-indolyl) carbonyl]propenonitrile

(Chemical Equation Presented) 2-Oxo-3-(indol-3-yl)propanonitrile 2 condensed with dimethylformamide dimethylacetal to yield the enaminonitrile 3. The latter reacted with 4-chloroaniline to yield the 4- chlorophenylaminoacrylonitrile 5. Reaction of 3 with hydrazine hydrate led to formation of pyrazole-4-carbonitrile 6. Compound 3 reacted with ethyl acetoacetate in refluxing acetic acid and in presence of ammonium acetate to yield the indolylpyridine 10. Enamine 3 reacted with 5(1H)-aminotriazole 13 and 3(5)-aminopyrazole 17 to yield the pyrimidine derivatives 15 and 19, respectively.

Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3-functionally substituted 3-acylindoles

(Chemical Equation Presented) 3-Substituted acylindoles 8 are obtained via refluxing carboxylic acids with indole in acetic anhydride solutions. The formed 3-substituted acylindole 8a is readily converted into 4-aminopyrazol-3- ylindoles 20, and into 22.

Microwave-assisted multicomponent reaction: An efficient synthesis of indolyl substituted and spiroxindole pyrido[2,3-d]pyrimidine derivatives

An efficient and catalyst-free protocol for the synthesis of a series of indole substituted or spiroxindole-consisted dihydropyrido[2,3-d]pyrimidine derivatives by one-pot three-component reaction of 2,6-diaminopyrimidin-4-one, various aryl aldehydes or isatins, and 3-cyanoacetyl indoles under microwave irradiation was investigated. The advantages of this methodology include high yields of products, short reaction time, easy work-up procedure and broad substrate scope.

A combination of experimental and TD-DFT investigations on the fluorescent detection of sulfite and bisulfite ions in aqueous solution via nucleophilic addition reaction

The selective detection of sulfite and bisulfite ions with anthracene-based compounds (CN1 and CN2) as chemo-dosimeters is reported using fluorescence changes in DMSO:HEPES (70:30%), v/v buffer solution (pH 7.4). Upon treatment with sulfite and bisulfite ions, the fluorescence of the probes gets enhanced significantly at 424 nm. The detection of these ions occurs through the nucleophilic addition at the vinylic C-atom of the probes, which terminates the photo-induced electron transfer (PET) process and consequently enhances the fluorescence. This detection mechanism is well supported by 1H NMR titration, HR-MS and DFT/TD-DFT calculations. The pseudo-first-order rate constants for the addition sulfite (at pH 7.4) and bisulfite (at pH 5) to CN1 are determined to be 3.22×10?3 and 5.02×10?3 s?1, respectively. The limits of detection for sulfite and bisulfite are found to be 1.85×10?7 and 1.56×10?7 M, respectively. The probe CN1 was successfully applied to the detection of bisulfite ion in real samples.

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

SMALL MOLECULE INHIBITORS OF RNA GUIDED ENDONUCLEASES

The present invention relates to the use of compounds of formula (I) as inhibitors of RNA guided endonucleases, e.g., Cas9 and Cpf1, and methods for the inhibition of the function of such RNA guided endonucleases, including their use in the treatment and

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.