281192-94-7

Usage

Type of compound

heterocyclic compound

Structure

contains a pyrrolopyridine ring system with a methyl group attached to the 1-position and a carbonyl group at the 2,3-positions

Potential biological activity

yes

Possible uses

as a building block for the synthesis of pharmaceuticals and other organic compounds

Safety precautions

handle with care, may pose risks to health and safety if not handled properly

Further research needed

yes, to fully understand and utilize the properties and potential applications of the compound.

Upstream product

• 5654-95-5 1H-pyrrolo[2,3-b]pyridine-2,3-dione 
• 74-88-4 methyl iodide 
• 271-63-6 7-Azaindole 
• 27257-15-4 1-methyl-1H-pyrrolo[2,3-b]pyridine 
• 281192-91-4 3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of 7-Azaisoindigo Derivatives

A series of novel 7-azaisoindigo derivatives 3-14 were designed, synthesized, and structurally characterized by IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analyses. Their antiproliferative activities were evaluated in a hormone-independent prostate cancer cell line DU145. Among them, compounds 8, 9, 14 showed the highest activities. Our study also showed that compounds 7, 11, 12 exhibited higher inhibitory activities on CDK2/cyclin A than that of the positive control meisoindigo. Western blot analysis on DU145 cells treated with compounds 7 and 9 demonstrated that 7-azaisoindigo derivatives could decrease the level of CDK2 activity (phosphorylation) and the expression of cyclin D1, and increase the expression of endogenous cyclin-dependent inhibitor p27.

[3 + 3] Formal Cycloadditions of Nitrones from Isatins and Azaoxyallyl Cations for Construction of Spirooxindoles

A [3 + 3] formal cycloaddition reaction between in situ formed azaoxyallyl cations and nitrones from isatins has been developed, furnishing a spectrum of spiro[1,2,4-oxadiazinan-5-one]oxindoles in good to excellent yields with excellent diastereoselectivity. This method provides direct and efficient access to potentially bioactive spirooxindoles incorporating a six-membered heterocyclic scaffold.

Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction

7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized.

Iodine-Catalyzed Oxidation of N-Substituted Indoles by using Chloramine-B: A Facile and Practical Approach to Isatins

An efficient method for the iodine-catalyzed oxidation of N-substituted indoles by using chloramine-B under mild reaction conditions was explored. This reaction was found to be tolerant to a variety of functional groups and provided the corresponding isatins in moderate to excellent yields. In addition, application of this method to the one-pot synthesis of 3-hydroxyoxindole and N-methylisatin oxime was realized.

Conjugate of Benzofuranone and Indole or Azaindole, and Preparation and Uses Thereof

The present invention relates to an oxo indirubin or isoindigo derivative, an oxo aza indirubin or isoindigo derivative, and their optical isomers, racemes, cis/trans isomers and pharmaceutically acceptable salts, which can be used for preparing a drug for treating or preventing diseases such as glucose metabolic disorder, inflammatory or autoimmune disease, neurodegenerative disease, a mental illness, tissue proliferation disease or tumors.

Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch

An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.

AlCl3/PCC-SiO2-promoted oxidation of azaindoles and indoles

A simple and efficient method is described for the oxidation of 7-azaindoles and indoles to 7-azaisatins and isatins using pyridinium chlorochromate-silica gel (PCC-SiO2) with the aid of Lewis acid catalyst aluminium chloride (AlCl3) in dichloroethane. Simplicity of the reaction conditions, easy workup procedure, and good yields are the key features of this protocol.

AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

Synthesis and antiproliferative activity of 7-azaindirubin-3′-oxime, a 7-aza isostere of the natural indirubin pharmacophore

The bis-indole alkaloid indirubin and its analogues bear a very interesting natural pharmacophore. They are recognized mainly as kinase inhibitors, but several other activities make them possible candidates for preclinical studies. Based on the previously reported activity of 7-bromoindirubin-3-oxime and its derivatives, the synthesis of indirubins bearing a heterocyclic nitrogen atom at position 7 was carried out. Herein, we report the first synthesis of 7-azaindirubin-3-oxime (12) as well as its antiproliferative activity against 57 cancer cell lines and its inhibitory activity against a series of kinases. 7-Azaindirubin (10) and its 3-oxime derivative (12) showed reduced activity as kinase inhibitors in comparison with other known indirubin derivatives, but antiproliferative activity with a best GI50 value of 0.77 μM.