159768-57-7

Basic information

• Product Name: 5-AMINO-3-CYANOINDOLE
• Synonyms: 5-AMINO-3-CYANOINDOLE;5-nitro-1H-indole-3-carbonitrile;5-Aminoindole-3-carbonitrile
• CAS NO: 159768-57-7
• Molecular Formula: C9H7N3
• Molecular Weight: 157.17
• Product Categories: pharmacetical
• Mol File: 159768-57-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 447.5°Cat760mmHg
• Flash Point: 224.5°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.00±0.30(Predicted)
• CAS DataBase Reference: 5-AMINO-3-CYANOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-3-CYANOINDOLE(159768-57-7)
• EPA Substance Registry System: 5-AMINO-3-CYANOINDOLE(159768-57-7)

Safety Data

• Hazardous Substances Data: 159768-57-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 35, p. 1019, 1992 DOI: 10.1021/jm00084a007

InChI:InChI=1/C9H7N3/c10-4-6-5-12-9-2-1-7(11)3-8(6)9/h1-3,5,12H,11H2

Upstream product

• 6146-52-7 5-nitroindole 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 
• 7147-14-0 5-nitro-1H-indole-3-carbonitrile 

Downstream Products

• 7147-14-0 5-nitro-1H-indole-3-carbonitrile 

Relevant articles and documents

N-(3-cyano-1H-indol-5-yl)isonicotinamide and N-(3-cyano-1H-indol-5-yl)-1H-benzo[d]imidazole-5-carboxamide derivatives: Novel amide-based xanthine oxidase inhibitors

Our previous work demonstrated that amide is an efficient linker to explore chemical space of xanthine oxidase (XO) inhibitors that are entirely different from febuxostat and topiroxostat. In this effort, with 3-cyano-1H-indol-5-yl as a key moiety, two series of amide-based XO inhibitors, N-(3-cyano-1H-indol-5-yl)isonicotinamides (2a-w) and N-(3-cyano-1H-indol-5-yl)-1H-benzo[d]imidazole-5-carboxamides (3a-i), were designed and synthesized. The structure-activity relationship investigation identified N-(3-cyano-1-cyclopentyl-1H-indol-5-yl)-1H-benzo[d]imidazole-5-carboxamide (3i, IC50 = 0.62 μM) as the most promising compound, with 14.4-fold higher in vitro inhibitory potency than allopurinol (IC50 = 8.91 μM). Molecular simulations provided reasonable interaction modes for the representative compounds. Furthermore, in vivo activity evaluation demonstrated that compound 3i (oral dose of 12.8 mg/kg) has obviously hypouricemic effect on a potassium oxonate induced hyperuricemic rat model. Cytotoxicity assay and ADME prediction also supported that 3i is an excellent lead for further exploration of amide-based XO inhibitors.

1-substituted-3-substituted-5-substituted amide-1H-indole compounds as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and particularly relates to 1-substituted-3-substituted-5-substitutedamide-1H-indole compounds as well as a preparation method and application thereof. The structural general formula I of the compounds is specifically shown in the specification. Pharmacological research shows that the compounds show a good effect in an in-vitro xanthine oxidase inhibitory activity test, and are free of obvious toxic and side effect. The preparation method of the 1-substituted-3-substituted-5-substituted amide-1H-indole compounds provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.