53269-35-5

Basic information

• Product Name: 3-FORMYL-1H-INDOLE-4-CARBONITRILE
• Synonyms: 3-FORMYL-1H-INDOLE-4-CARBONITRILE
• CAS NO: 53269-35-5
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.17
• Mol File: 53269-35-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-FORMYL-1H-INDOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-1H-INDOLE-4-CARBONITRILE(53269-35-5)
• EPA Substance Registry System: 3-FORMYL-1H-INDOLE-4-CARBONITRILE(53269-35-5)

Safety Data

• Hazardous Substances Data: 53269-35-5(Hazardous Substances Data)

Usage

General Description

3-FORMYL-1H-INDOLE-4-CARBONITRILE is a chemical compound with the molecular formula C10H6N2O, primarily used in pharmaceutical and chemical research. It is a derivative of indole, and its structure contains a formyl group and a carbonitrile group. 3-FORMYL-1H-INDOLE-4-CARBONITRILE has been studied for its potential pharmacological properties, particularly as an inhibitor of certain enzymes and as a potential building block for the synthesis of other biologically active compounds. Its unique structure and potential functional groups make it an interesting target for further research and development in the field of medicinal chemistry.

Upstream product

• 16136-52-0 4-cyanoindole 
• 298-12-4 Glyoxilic acid 
• 487-89-8 Indole-3-carboxaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 544-92-3 copper(I) cyanide 
• 141692-10-6 (3-formylindol-4-yl)thallium (III) bistrifluoroacetate 
• 72527-73-2 4-iodo-indole-3-carboxaldehyde 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 77963-70-3 RU 27849 
• 147108-60-9 4-(N-phenylacetylamino)-1,3,4,5-tetrahydrobenz[cd]indole 
• 16136-52-0 4-cyanoindole 
• 1074-86-8 4-formyl indole 
• 863407-44-7 trans-3-[4-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide 
• 863407-39-0 3-formyl-1-(4-toluenesulfonyl)-1H-indole-4-carbonitrile 
• 103754-50-3 4-cyanoindole-3-methanol 
• 105907-63-9 4-cyano-3-dimethylaminomethylindole 

Relevant articles and documents

A Scalable Synthesis of the Blue Fluorescent Amino Acid 4-Cyanotryptophan and the Fmoc Derivative: Utility Demonstrated with the Influenza M2 Peptide Tetramer

A scalable synthesis of the Fmoc-protected blue fluorescent amino acid, l-4-cyanotryptophan (W4CN), that exploits an enantioselective phase transfer-catalyzed alkylation is reported. The red-shifted emission of water-exposed W4CN residues was leveraged to investigate the solvation state of tryptophan (Trp) residues within the influenza M2 proton channel. The correlation of the channel's conformation (i.e., open or closed) with the fluorescence spectrum of a mutated W4CN residue suggests that the channel's conformational state does not impact the hydration status of the Trp residues.

Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid

Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.

Elaboration of thorough simplified vinca alkaloids as antimitotic agents based on pharmacophore similarity

Thorough simplification of vinca alkaloids based on pharmacophore similarity has been conducted. A concise process for the syntheses of target compounds was successfully developed with yields from poor to excellent (19-98%). Cell growth inhibitory activities of these synthesized compounds were evaluated in five cancer cell lines including MCF-7, MDA-MB-231, HepG2, HepG2/ADM and K562. Almost all compounds exhibited moderate antitumor activity with optimal IC50 value of 0.89 ± 0.07 μM in MCF-7 cells. Investigation of structure-activity relationship (SAR) indicates that electron-withdraw substituents on the ring contribute to the enhancement of the antitumor activities. The simplified vinca alkaloids are confirmed as antimitotic agents, which inhibit the polymerization of tubulin just like vinblastine.