5457-28-3 Usage
Description
3-Cyanoindole, with the chemical formula C10H6N2 and CAS number 5457-28-3, is an organic compound that serves as a versatile building block in organic synthesis. It features a cyano group attached to an indole nucleus, which provides a range of reactivity and functional group compatibility, making it a valuable intermediate for the synthesis of various biologically active molecules and pharmaceutical agents.
Uses
Used in Pharmaceutical and Medicinal Chemistry:
3-Cyanoindole is used as a reactant for the preparation of a variety of compounds with potential therapeutic applications. Its reactivity and structural features make it suitable for the synthesis of:
Tryptophan dioxygenase inhibitors, such as pyridyl-ethenyl-indoles, which have potential as anticancer and immunomodulatory agents.
Inhibitors of the C-terminal domain of RNA polymerase II, which possess antitumor activities and can be used in cancer treatment.
4-Substituted β-lactams, a class of antibiotics with broad-spectrum antimicrobial properties.
Biologically active indoles, which have diverse pharmacological effects and can be used in the development of new drugs.
Inhibitors of glycogen synthase kinase 3β (GSK-3), which are involved in the regulation of various cellular processes and have potential applications in the treatment of neurodegenerative diseases and other conditions.
HIV-1 integrase inhibitors, which can be used in the development of antiretroviral therapies for the treatment of HIV/AIDS.
Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors, which have potential applications in the treatment of cancer and viral infections.
Used in Organic Synthesis and Chemical Research:
3-Cyanoindole is also used as a reactant in various organic synthesis reactions, such as:
Intramolecular oxidative C-H coupling reactions, which have applications in medium-ring synthesis techniques and the preparation of complex molecular structures.
The synthesis of the aziridinomitosene skeleton, which is a key structural motif in the development of novel antiviral agents and other bioactive compounds.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 5, p. 656, 1973Tetrahedron, 50, p. 6549, 1994 DOI: 10.1016/S0040-4020(01)89685-XTetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3
Check Digit Verification of cas no
The CAS Registry Mumber 5457-28-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,5 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5457-28:
(6*5)+(5*4)+(4*5)+(3*7)+(2*2)+(1*8)=103
103 % 10 = 3
So 5457-28-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
5457-28-3Relevant articles and documents
Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical
Shee, Maniklal,Shah, Sk. Sheriff,Singh, N. D. Pradeep
supporting information, p. 14070 - 14074 (2020/10/12)
This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.
Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
supporting information, p. 3110 - 3115 (2020/07/04)
Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
Synthesis of sufamides of indole series
Suzdalev,Den'Kina
scheme or table, p. 1675 - 1677 (2010/04/29)
The reaction of indoles with chlorosulfonyl isocyanate yields indolylcarbonylsulfamoyl chlorides. Their reaction with amines afforded a series of indole-containing sulfamides.
