5192-23-4 Usage
Description
4-Aminoindole is an indole derivative characterized by its greenish-grey to tan powder appearance. It has been assessed for its cytokinin activity through the tobacco pith callus bioassay and can be synthesized by reacting 2,6-dinitrotoluene and N,N-dimethylformamide dimethylacetal in anhydrous DMF.
Uses
4-Aminoindole is used as a reactant for the preparation of various compounds, including:
1. Macrolactam tumour promoter indolactam V
2. Tricyclic structure of 2-substituted-pyrrolo[2,3-h]quinolin-4-one
3. 4-azidoindole
Additionally, 4-Aminoindole serves as a starting material or intermediate in the synthesis of different types of inhibitors and antagonists, such as:
Used in Pharmaceutical Industry:
4-Aminoindole is used as a reactant for the synthesis of inhibitors of bacterial thymidylate synthase, which are essential in the development of antibiotics and antiviral medications.
Used in Anticancer Applications:
4-Aminoindole is used as a mimetic of non-alkaloid toxin lignan anticancer and antiviral agent Podophyllotoxin (PPT), contributing to the development of novel cancer treatments.
Used in Hedgehog Pathway Inhibition:
4-Aminoindole is used as an inhibitor of Gli1-mediated transcription in the Hedgehog pathway, which plays a role in the regulation of cell growth and differentiation, and is often dysregulated in various cancers.
Used in Immunology:
4-Aminoindole is used as a Protein kinase C θ (PKCθ) inhibitor, which has potential applications in the treatment of autoimmune diseases and T-cell mediated disorders.
Used in HIV Treatment:
4-Aminoindole is used as an indolic non-peptidic HIV protease inhibitor, which can help in the development of antiretroviral drugs for HIV/AIDS treatment.
Used in Pain Management:
4-Aminoindole is used as a transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonist, which may have applications in the management of chronic pain conditions.
Used in Inflammation and Pain Management:
4-Aminoindole is used as a Cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitor, which can be beneficial in the development of anti-inflammatory and analgesic drugs.
Used in Metabolic Disorders:
4-Aminoindole is used as an 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) inhibitor, which may have potential applications in the treatment of metabolic disorders such as diabetes and obesity.
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 5130, 1983 DOI: 10.1021/jo00173a071
Check Digit Verification of cas no
The CAS Registry Mumber 5192-23-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,9 and 2 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5192-23:
(6*5)+(5*1)+(4*9)+(3*2)+(2*2)+(1*3)=84
84 % 10 = 4
So 5192-23-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,9H2
5192-23-4Relevant articles and documents
Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 1530 - 1534 (2021/03/08)
The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
