869335-73-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is used as a chemical intermediate for the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs with specific therapeutic properties. 4-CHLORO-3-IODO-1H-PYRROLO[2,3-B]PYRIDINE's ability to be modified and incorporated into larger molecules allows for the exploration of its potential in treating various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is utilized as a precursor in the production of agrochemicals. Its structural features and reactivity contribute to the creation of compounds with pesticidal, herbicidal, or other agricultural applications. 4-CHLORO-3-IODO-1H-PYRROLO[2,3-B]PYRIDINE can be a key component in the development of innovative and effective solutions for crop protection and enhancement of agricultural productivity.
Overall, the versatility of 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine in both the pharmaceutical and agrochemical industries highlights its importance as a building block for the synthesis of a wide range of compounds. Its specific applications and uses will depend on the intended purpose and the requirements of each industry.

InChI:InChI=1/C7H4ClIN2/c8-4-1-2-10-7-6(4)5(9)3-11-7/h1-3H,(H,10,11)

Upstream product

• 55052-28-3 4-chloro-7-azaindole 
• 918515-16-9 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 
• 920965-87-3 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 271-63-6 7-Azaindole 

Downstream Products

• 1613710-11-4 3-(4-(azetidin-1-ylsulfonyl)phenyl)-4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1613710-10-3 N,N-diethyl-2-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-09-0 N,N-dimethyl-2-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-08-9 N,N-diethyl-3-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-07-8 N,N-dimethyl-4-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-06-7 N-(tert-butyl)-N-methyl-3-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-05-6 N,N-dimethyl-3-(4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide 
• 1613710-01-2 3-(2,4-dimethoxyphenyl)-4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1613709-44-6 3-(3-chlorophenyl)-4-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1613712-53-0 C₂₅H₁₈ClFN₂O₃S 
• 1613712-39-2 C₂₅H₁₈F₂N₂O₃S₂ 
• 1613712-36-9 C₂₁H₁₆ClFN₂O₃S 
• 1613712-37-0 C₂₅H₁₉FN₂O₃S₂ 
• 1613712-34-7 C₂₀H₁₆N₂O₃S 

Relevant academic research and scientific papers

Inhibitors of the Hippo Pathway Kinases STK3/MST2 and STK4/MST1 Have Utility for the Treatment of Acute Myeloid Leukemia

Serine/threonine-protein kinases 3 and 4 (STK3 and STK4, respectively) are key components of the Hippo signaling pathway, which regulates cell proliferation and death and provides a potential therapeutic target for acute myeloid leukemia (AML). Herein, we

Discovery of a novel indole pharmacophore for the irreversible inhibition of myeloperoxidase (MPO)

Myeloperoxidase (MPO) activity and subsequent generation of hypochlorous acid has been associated with the killing of host-invading microorganisms (e.g. bacteria, viruses, and fungi). However, during oxidative stress, high MPO activity can damage host tissue and is linked to several chronic inflammatory conditions. Herein, we describe the development of a novel biaryl, indole-pyrazole series of irreversible mechanism-based inhibitors of MPO. Derived from an indole-containing high-throughput screen hit, optimization efforts resulted in potent and selective 6-substituted indoles with good oral bioavailability and in vivo activity.

Cu(II)-catalyzed sulfonylation of 7-azaindoles using DABSO as SO2-Source and its mechanistic study

DABSO mediated sulfonylation of iodinated 7-azaindoles was achieved for the first time through sulfonylative Suzuki-Miyaura cross coupling (SMC) reaction under mild conditions giving good yields of sulfonylated 7-azaindole derivatives. Interestingly, control experiments suggest that present method involves in-situ generation of ArSO2 free radical followed by the key steps of SMC reaction. Scope of the reaction was explored with both electronically different and bulky group carrying boronic acids as coupling partner. The sulfonylation is scalable and occurred selectively at iodo group, irrespective of its position on azaindole. Moreover, the proposed mechanism has been supported by electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations.

PYRROLO[2,3-B]PYRIDINE COMPOUNDS AND THEIR USE IN THE TREATMENT OF CANCER

The present application relates to a compound of Formula I, or a salt, hydrate or solvate thereof, as defined herein. The present compounds are found to have pharmacological effects, particularly at MRCK. Further provided are pharmaceutical compositions comprising said compounds. The present invention also relates to the use of these compounds as therapeutic agents, in particular, for the treatment and/or prevention of proliferative diseases, such as cancer.

Synthesis and structure?activity?relationship of 3,4?Diaryl?1H?pyrrolo[2,3?b]pyridines as irreversible Inhibitors of mutant EGFR?L858R/T790M

The epidermal growth factor receptor (EGFR) is a well?validated drug target for the treatment of non?small cell lung cancer. Here we present an optimization approach and preliminary structure?activity relationship for 1H?pyrrolo[2,3?b]pyridines as covalent irreversible mutant EGFR inhibitors. We synthesized a focused library to investigate the effect of different aromatic substituents in the 4?position of this scaffold, interacting with the gatekeeper. We determined the activity of the synthesized compounds mutant EGFR enzyme assays and determined the selectivity over the wild type.

NUCLEOSIDE ANALOGUES FOR THE TREATMENT OF PARASITIC INFECTIONS

The present invention relates to novel nucleoside analogues and compositions containing said nucleoside analogues. Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the diagnosis, prevention and/or treatment of parasitic infections, more specifically for use in the diagnosis, prevention and/or treatment of a Trypanosoma infection.

Discovery of Pyrrolo[2,3- b]pyridine (1,7-Dideazapurine) Nucleoside Analogues as Anti- Trypanosoma cruzi Agents

Trypanosoma cruzi is the causative pathogen of Chagas disease and the main culprit for cardiac-related mortality in Latin-America triggered by an infective agent. Incapable of synthesizing purines de novo, this parasite depends on acquisition and processing of host-derived purines, making purine (nucleoside) analogues a potential source of antitrypanosomal agents. In this respect, hitherto 7-deazaadenosine (tubercidin) analogues attracted most attention. Here, we investigated analogues with an additional nitrogen (N1) removed. Structure-activity relationship investigation showed that C7 modification afforded analogues with potent antitrypanosomal activity. Halogens and small, linear carbon-based substituents were preferred. Compound 11 proved most potent in vitro, showed full suppression of parasitemia in a mouse model of acute infection, and elicited 100% animal survival after oral dosing at 25 mg/kg b.i.d. for 5 and 15 days. Cyclophosphamide-induced immunosuppression led to recrudescence. Washout experiments demonstrated a lack of complete clearance of infected cell cultures, potentially explaining the in vivo results.

Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature

A halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its importance in lowering the activation barrier for this reaction, the presence of radical intermediates in a reaction mixture, and the regioselectivity of the reaction have been demonstrated with several control experiments, spectroscopic analysis, and quantum chemical calculations. Allowing the formation of the halogen bond may offer a new strategy to generate the reactive radical intermediates and to enable the otherwise elusive electron-catalyzed reactions under mild reaction conditions.

Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution

The catalytic enantioselective synthesis of 3-aryl-substituted pyrrolopyrimidines (PPYs), a common motif in drug discovery, is achieved through a kinetic resolution via quaternary ammonium salt-catalyzed nucleophilic aromatic substitution (SNAr). Both enantioenriched products and starting materials can be functionalized with no observed racemization to give enantiodivergent access to diverse chiral analogues of an important class of kinase inhibitor. One of the compounds was found to be a potent and selective inhibitor of breast tumor kinase.

Synthesis of a 3′-C-ethynyl-β-D-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides

A focused nucleoside library was constructed around a 3′-C-ethynyl-D-ribofuranose sugar scaffold, which was coupled to variously modified purine nucleobases. The resulting nucleosides were probed for their ability to inhibit tumor cell proliferation, as well as for their activity against a panel of relevant human viruses. While C6-aryl substituted purine nucleosides were found to be weakly active, several C7-substituted 7-deazapurine nucleosides elicited potent antiproliferative activity. Their activity spectrum was evaluated in the NCI-60 tumor cell line panel indicating activity against several solid tumor derived cell lines. Analog 32, equipped with a 7-deaza 7-chloro-6-amino-purin-9-yl base was evaluated in a metastatic breast tumor (MDA-MB-231-LM2) xenograft model. It inhibited both tumor growth and reduced the formation of lung metastases as revealed by BLI analysis. The dideazanucleoside analog 66 showed interesting activity against hCMV. These results highlight the potential advantages of recombining known sugar and nucleobase motifs as a library design strategy to discover novel antiviral or antitumor agents.