956003-24-0

Basic information

• Product Name: 3-IODO-1H-PYRROLO[2,3-C]PYRIDINE
• Synonyms: 3-IODO-1H-PYRROLO[2,3-C]PYRIDINE;3-IODO-6-AZAINDOLE
• CAS NO: 956003-24-0
• Molecular Formula: C₇H₅IN₂
• Molecular Weight: 244.031
• Mol File: 956003-24-0.mol

Chemical Properties

• Boiling Point: 380.5°C at 760 mmHg
• Flash Point: 183.9°C
• Appearance: /
• Density: 2.082
• Vapor Pressure: 1.18E-05mmHg at 25°C
• Refractive Index: 1.787
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.16±0.40(Predicted)
• CAS DataBase Reference: 3-IODO-1H-PYRROLO[2,3-C]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODO-1H-PYRROLO[2,3-C]PYRIDINE(956003-24-0)
• EPA Substance Registry System: 3-IODO-1H-PYRROLO[2,3-C]PYRIDINE(956003-24-0)

Safety Data

• Hazardous Substances Data: 956003-24-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Drug Discovery:
3-Iodo-1H-pyrrolo[2,3-c]pyridine is used as a chemical intermediate for the synthesis of various biologically active compounds due to its unique structure and reactivity. It serves as a valuable building block in the development of novel therapeutics for the treatment of various diseases.
Used in Anti-Cancer Applications:
3-Iodo-1H-pyrrolo[2,3-c]pyridine is used as a potential anti-cancer agent, exhibiting diverse pharmacological activities that may contribute to the development of new cancer treatments. Its unique structure and reactivity allow for the exploration of its potential in targeting and inhibiting cancer cell growth and proliferation.
Used in Anti-Inflammatory Applications:
3-Iodo-1H-pyrrolo[2,3-c]pyridine is used as a potential anti-inflammatory agent, with its pharmacological properties suggesting a role in modulating inflammatory responses. This may lead to the development of new treatments for inflammatory diseases and conditions.
Used in Anti-Microbial Applications:
3-Iodo-1H-pyrrolo[2,3-c]pyridine is used as a potential anti-microbial agent, with its diverse pharmacological activities indicating a possible role in combating microbial infections. This may contribute to the development of new antimicrobial therapies for the treatment of various infectious diseases.

InChI:InChI=1/C7H5IN2/c8-6-3-10-7-4-9-2-1-5(6)7/h1-4,10H

Upstream product

• 271-29-4 6-azaindole 

Downstream Products

• 1174038-59-5 tert-butyl 3-iodo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 
• 1316228-55-3 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridine 
• 1316228-31-5 C₂₁H₂₁N₅O₂ 
• 887115-55-1 1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine 
• 1353967-23-3 2-(5-chloro-2-fluoro-phenyl)-4-[1-(2-methoxy-ethyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-[1,8]naphthyridine 

Relevant articles and documents

A simple and facile iodination method of didechlorotiacumicin B and aromatic compounds

Tiacumicin B (also known as fidaxomicin or difimicin) is a marketed 18-membered macrolide antibiotic for the treatment of Clostridium difficile infections. Tiacumicin B is structurally characterized with two chlorine atoms substituted on the aromatic ring

Developing DYRK inhibitors derived from the meridianins as a means of increasing levels of NFAT in the nucleus

A structure-activity relationship has been developed around the meridianin scaffold for inhibition of Dyrk1a. The compounds have been focussed on the inhibition of kinase Dyrk1a, as a means to retain the transcription factor NFAT in the nucleus. NFAT is responsible for up-regulation of genes responsible for the induction of a slow, oxidative skeletal muscle phenotype, which may be an effective treatment for diseases where exercise capacity is compromised. The SAR showed that while strong Dyrk1a binding was possible with the meridianin scaffold the compounds have no effect on NFAT localisation, however, by moving from the indole to a 6-azaindole scaffold both potent Dyrk1a binding and increased NFAT residence time in the nucleus were obtained – properties not observed with the reported Dyrk1a inhibitors. One compound was shown to be effective in an ex vivo muscle fiber assay. The increased biological activity is thought to arise from the added interaction between the azaindole nitrogen and the lysine residue in the back pocket.

Rapid preparation of triazolyl substituted NH-heterocyclic kinase inhibitors via one-pot Sonogashira coupling-TMS-deprotection-CuAAC sequence

The one-pot, three-component Sonogashira coupling-TMS-deprotection-CuAAC ("click") sequence is the key reaction for the rapid synthesis of triazolyl substituted N-Boc protected NH-heterocycles, such as indole, indazole, 4-, 5-, 6-, and 7-azaindoles, 4,7-diazaindole, 7-deazapurines, pyrrole, pyrazole, and imidazole. Subsequently, the protective group was readily removed to give the corresponding triazolyl derivatives of these tremendously important NH-heterocycles. All compounds have been tested in a broad panel of kinase assays. Several compounds, 8f, 8h, 8k, and 8l, have been shown to inhibit the kinase PDK1, a target with high oncology relevance, and thus they are promising lead structures for the development of more active derivatives. The X-ray structure analysis of compound 8f in complex with PDK1 has revealed the detailed binding mode of the molecule in the kinase. The Royal Society of Chemistry 2011.

4 (PYRROLO[2,3-C]PYRIDINE-3-YL)PYRIMIDIN-2-AMINE DERIVATIVES

Compounds of the formula (I), in which R1, R2, R3, R4 and R5 have the meanings indicated in Claim 1, are inhibitors of cell proliferation/cell vitality and can be employed for the treatment of tumours