5654-95-5

Usage

Uses

Used in Plant Growth Regulation:
1H-Pyrrolo[2,3-b]pyridine-2,3-dione is used as a plant growth regulator and synthetic auxin for promoting the growth and differentiation of cells. It is commonly utilized in tissue culture labs to enhance plant development and improve crop yields.
Used in Agriculture:
In the agricultural industry, 1H-Pyrrolo[2,3-b]pyridine-2,3-dione is used as a herbicide to control the growth of unwanted plants. Its ability to regulate plant growth helps in managing weed populations and maintaining the health of desired crops.
Used in Pharmaceutical Industry:
Due to its biological activity, 1H-Pyrrolo[2,3-b]pyridine-2,3-dione has potential applications in the pharmaceutical industry. Its specific properties may be harnessed for the development of new drugs or therapeutic agents.
Safety Precautions:
It is crucial to handle 1H-Pyrrolo[2,3-b]pyridine-2,3-dione with care, as it can be harmful if ingested or inhaled. Additionally, it may cause irritation to the skin and eyes, necessitating proper safety measures during its use and storage.

InChI:InChI=1/C7H4N2O2/c10-5-4-2-1-3-8-6(4)9-7(5)11/h1-3H,(H,8,9,10,11)

Upstream product

• 126807-18-9 1H-pyrrolo[2,3-b]pyridine-2,3-dione-3-oxime 
• 5654-97-7 7-azaoxindole 
• 113423-51-1 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one 
• 21038-63-1 3-azaisatoic anhydride 
• 271-63-6 7-Azaindole 
• 53277-42-2 1-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone 
• 27420-41-3 2-hydroxy-4H-pyrido<1,2-a>pyrimidin-4-one 
• 1202876-67-2 2,3-dibromo-3H-pyrrole-[2,3-b]pyridine 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 86847-66-7 2,2-dimethyl-N-(3-methylpyridin-2-yl)propionamide 
• 1071087-00-7 3-(2-trimetylacetylamino)pyridylacetic acid 
• 10592-27-5 7-azaindoline 

Downstream Products

• 1261038-81-6 (R)-3-hydroxy-3-(2-oxo-2-phenylethyl)-7-azaindolin-2-one 
• 1383677-32-4 tert-butyl 1-(4-(methylcarbamoyl)-3-phenyl-1,8-naphthyridin-2-yl)ethylcarbamate 
• 1383677-31-3 2-(1-(tert-butoxycarbonylamino)ethyl)-3-phenyl-1,8-naphthyridine-4-carboxylic acid 
• 281192-94-7 N-Methyl-7-azaisatin 
• 443986-73-0 C₂₆H₁₉N₃O₂ 
• 1115389-44-0 C₁₅H₁₁FN₂O₂ 
• 126807-18-9 1H-pyrrolo[2,3-b]pyridine-2,3-dione-3-oxime 

Relevant academic research and scientific papers

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

AMINE OR (THIO)AMIDE CONTAINING LXR MODULATORS

The present invention relates to derivatives of formula (I) which bind to the liver X receptor (LXRα and/or LXRβ) and act preferably as inverse agonists of LXR.

An efficient method based on indoles for the synthesis of isatins by taking advantage of I2O5 as oxidant

An efficient method to synthesize isatins based on indoles by using inorganic hypervalent I2O5 has been explored in good yields, which successfully realized the transformation from indoles to isatins under metal-free, mild condition

7,7′-Diazaindirubin - A small molecule inhibitor of casein kinase 2 in vitro and in cells

Aza- and diaza-bisindoles were synthesized by coupling of 7-azaisatin, 7-azaoxindol, 7-azaindoxyl acetate, and their non-aza counterparts, respectively. Whereas 7,7′-diazaindigo (10) and 7,7′-diazaisoindigo (11) did not show antiproliferative activity in several human tumor cell lines up to 100 μM, 7-azaindirubin (12) and 7′-azaindirubin (13) were more active than the parent molecule, indirubin, in LXFL529L cells (human large cell lung tumor xenograft), and 7,7′-diazaindirubin (14) was exhibiting substantially enhanced growth inhibitory activity in these cells. In the NCI 60 cell line panel, 14 displayed antiproliferative activity preferentially in certain melanoma and non-small cell lung cancer cells. In contrast to the potent serine/threonine/tyrosine kinase inhibition observed for indirubins, kinase inhibition profiling of 14 in 220 kinases revealed largely a loss of kinase inhibitory activity towards most kinases, with retained inhibitory activity for just a few kinases. At 1 μM concentration, especially casein kinases CK1γ3, CK2α, CK2α2, and SIK were inhibited by more than 50%. In cell-based assays, 14 markedly affected CK2-mediated signaling in various human tumor cells. In MCF7 cells, 14 induced cell cycle arrest at G1 and G2/M and apoptosis, whereas CK2-deficient MCF7 cells were resistant. These findings reveal a novel key mechanism of action for 14, suggesting primarily CK2 inhibition to be causally related to growth inhibition of human tumor cells.

Ylide mediated carbonyl homologations for the preparation of isatin derivatives

An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.

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.

7-azaindirubins, 7'-azaindirubins, 7-7'-diazaindirubin and the corresponding 3'-oxime ether derivates: production thereof, their production and use as a medicament

The present invention relates to 7-azaindirubins (1), 7'-azaindirubins (2), and 7,7'-diaza-indirubins (3), wherein E, R1 and R2 have the meanings detailed in the description, their production and use as a medicament for treating cancer, neurodegenerative diseases, bipolar disorders, inflammatory and infectious diseases, including viral diseases. Depending on structure, these indirubins act as inhibitors of various kinases involved in tumor cell growth, and, most notably, as inhibitors of human tumor cell proliferation. As compared to indirubins bearing identical substituents but no hetero atoms in position 7 and 7', the activity of the compounds according to the present invention is increased and the propensity to get metabolized by CYP450s is reduced, resulting in improved metabolic stability.

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.

Substituted pyridopyrimidinones: oxidation of 2-hydroxypyrido [1,2-a]pyrimidin-4(H)-one

A simple method for the oxidation of 2-hydroxypyrido[1,2-a]pyrimidin-4(H)- one is described. Treatment of the title compound with selenium dioxide in dioxane/water, followed by warming leads directly to 1H-pyrrolo[2,3-fo]pyridine- 2,3-dione. The method is shown to be effective for preparation of the last compound which is used as a synthon for some antihypertensive agents.

Use of pyridinium chlorochromate and reusable polyaniline salt catalyst combination for the oxidation of indoles

A novel method is described herein for the simple, convenient and efficient oxidation of indoles to isatins using pyridinium chlorochromate with the aid of polyaniline salt catalyst at room temperature or at reflux in dichloroethane. Interestingly, oxidation of 3-alkyl indoles by this procedure gave 3-hydroxy 3-alkyl oxindoles. On the other hand, indol-3-alkanols gave mixtures of isatins and 3-formyl indoles. This is the first example of use of polyaniline as a catalyst in oxidation reaction.