17380-18-6

Basic information

• Product Name: 5-CYANOINDOLE-3-CARBOXALDEHYDE
• Synonyms: RARECHEM AH BS 0094;3-FORMYL-1H-INDOLE-5-CARBONITRILE;5-CYANOINDOLE-3-ALDEHYDE;5-CYANOINDOLE-3-CARBOXALDEHYDE;5-CYANOINDOLE-3-CARBOXYALDEHYDE;3-formyl-indole-5-carbonitril;3-formylindole-5-carbonitrile;5-Cyano-1H-indole-3-carboxaldehyde
• CAS NO: 17380-18-6
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.17
• Product Categories: Aldehydes;Building Blocks;C10;C10-C12;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Indoles;Organic Building Blocks
• Mol File: 17380-18-6.mol
• Article Data: 29

Chemical Properties

• Melting Point: 248-253 °C
• Boiling Point: 429.565 °C at 760 mmHg
• Flash Point: 213.593 °C
• Appearance: white to off-white crystalline powder
• Density: 1.337 g/cm³
• Vapor Pressure: 1.39E-07mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.12±0.30(Predicted)
• CAS DataBase Reference: 5-CYANOINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CYANOINDOLE-3-CARBOXALDEHYDE(17380-18-6)
• EPA Substance Registry System: 5-CYANOINDOLE-3-CARBOXALDEHYDE(17380-18-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 17380-18-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 17380-18-6 differently. You can refer to the following data:
1. ? ;Reactant for synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators1? ;Reactant for enantioselective preparation of antifungal agents2? ;Reactant for synthesis of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-13? ;Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents4? ;Reactant for preparation of indolecarboxamide derivatives as antitumor agents5? ;Reactant for synthesis of a selective serotonin reuptake inhibitor6
2. Reactant for synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulatorsReactant for enantioselective preparation of antifungal agentsReactant for synthesis of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-1Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agentsReactant for preparation of indolecarboxamide derivatives as antitumor agentsReactant for synthesis of a selective serotonin reuptake inhibitor

InChI:InChI=1/C10H6N2O/c11-4-7-1-2-10-9(3-7)8(6-13)5-12-10/h1-3,5-6,12H

Upstream product

• 15861-24-2 1H-indole-5-carbonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 100-97-0 hexamethylenetetramine 
• 10075-50-0 5-bromo-1H-indole 
• 298-12-4 Glyoxilic acid 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 25514-67-4 3-Dimethylaminomethylindole-5-carbonitrile 

Downstream Products

• 1360583-83-0 dimethyl 2-(1-benzyl-5-cyano-1H-indol-3-yl)cyclopropane-1,1-dicarboxylate 
• 1360583-77-2 dimethyl 2-[(1-benzyl-5-cyano-1H-indol-3-yl)methylene]malonate 
• 1360583-74-9 1-benzyl-5-cyano-1H-indole-3-carbaldehyde 
• 1415234-12-6 C₁₈H₉Cl₂N₃ 
• 468717-95-5 (+)-(1S,2S)-ethyl 2-(5-cyano-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate 
• 588688-44-2 C₁₀H₉NO₂ 
• 1640122-64-0 N-acetyl-3-(4-methoxyphenyl)-3-methylindoline-5-carbonitrile 
• 1640122-65-1 ethyl-N-acetyl-3-(4-methoxyphenyl)-3-methylindoline-5-carboxylate 

Relevant articles and documents

Search for a 5-CT alternative. In vitro and in vivo evaluation of novel pharmacological tools: 3-(1-alkyl-1H-imidazol-5-yl)-1H-indole-5-carboxamides, low-basicity 5-HT7 receptor agonists

Close structural analogues of 5-carboxamidotryptamine (5-CT) based on the newly discovered indole-imidazole scaffold were synthesized and evaluated to search for a 5-HT7 receptor agonist of higher selectivity. In vitro drug-likeness studies and in vivo pharmacological evaluation of potent and selective low-basicity 5-HT7 receptor agonists, previously published 7 (3-(1-ethyl-1H-imidazol-5-yl)-1H-indole-5-carboxamide, AH-494) and 13 (3-(1-methyl-1H-imidazol-5-yl)-1H-indole-5-carboxamide), have supported their usefulness as pharmacological tools. Comprehensive in vitro comparison studies between 7, 13 and the commonly used 5-CT showed their very similar ADMET properties. Compound 7 at 1 mg kg?1 reversed MK-801-induced disruption in novel object recognition in mice and alleviated stress-induced hyperthermia (SIH) at high doses. Taking into account both in vitro and in vivo data, 7 and 13 may be considered as alternatives to 5-CT as pharmacological tools with important additional benefit associated with their low-basicity: high selectivity over 5-HT1AR.

1-alkyl-5-tetrazolyl/pyrimidinone-1H-indole-3-formonitrile compounds as well as preparation method and application thereof

The invention relates to 1-alkyl-5-tetrazolyl/pyrimidinone-1H-indole-3-formonitrile compounds as well as a preparation method and application thereof, belonging to the technical field of medicines. The invention provides a series of 1-alkyl-5-(1H-tetrazol-5-yl)/(4-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-formonitrile compounds, and in-vitro xanthine oxidase inhibitory activity tests are carried out on the prepared compounds by adopting an ultraviolet spectrophotometric method; and results show that the prepared compounds have obvious xanthine oxidase inhibitory activity. In acute hyperuricemia rat model tests, the compounds can significantly reduce the uric acid level of serum, and have good in-depth research value as novel xanthine oxidase inhibitors.

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.