757978-19-1

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)-;1-Benzenesulfonyl-5-broMo-3-iodo-7-azaindole;5-Bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine;1-(Benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine
• CAS NO: 757978-19-1
• Molecular Formula: C₁₃H₈BrIN₂O₂S
• Molecular Weight: 463.08829
• Mol File: 757978-19-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)-(757978-19-1)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)-(757978-19-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 757978-19-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-iodo-1-(phenylsulfonyl)is used as a key intermediate in organic synthesis for the preparation of a variety of complex organic molecules. Its unique structure allows for multiple points of reactivity, facilitating the construction of diverse chemical entities.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-iodo-1-(phenylsulfonyl)is utilized as a building block for the synthesis of biologically active compounds. The presence of the phenylsulfonyl group and halogen atoms (bromine and iodine) makes it particularly suitable for the development of new pharmaceutical agents, potentially leading to the discovery of novel treatments for various diseases.
Used in Cross-Coupling Reactions:
1H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-iodo-1-(phenylsulfonyl)is employed as a reactant in cross-coupling reactions, a class of chemical reactions that are fundamental in modern organic synthesis. The phenylsulfonyl group enhances the reactivity of the molecule, making it a preferred candidate for such reactions, which are often used to form carbon-carbon bonds.
Used in the Development of Pharmaceuticals:
1H-Pyrrolo[2,3-b]pyridine, 5-broMo-3-iodo-1-(phenylsulfonyl)is used as a precursor in the pharmaceutical industry for the synthesis of potential drug candidates. The bromine and iodine atoms provide opportunities for further functionalization, which can be crucial for optimizing the pharmacological properties of the resulting compounds, such as their potency, selectivity, and pharmacokinetics.
Used in the Development of Agrochemicals:
Similarly, in agrochemistry, 1H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-iodo-1-(phenylsulfonyl)is used to develop new agrochemicals with improved efficacy and selectivity. The versatility of the molecule allows for the design of compounds that can target specific pests or diseases while minimizing environmental impact.

Upstream product

• 757978-18-0 3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine 
• 98-09-9 benzenesulfonyl chloride 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 1001414-15-8 1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide 
• 757978-20-4 1-Benzenesulfonyl-5-bromo-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1046793-47-8 2-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thiazole 
• 1261082-93-2 3-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline 
• 1261082-79-4 N-(5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-yl)benzenesulfonamide 
• 1261082-86-3 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-amine 
• 1261082-87-4 N-(3-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)benzenesulfonamide 
• 1261082-90-9 3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline 
• 1261082-88-5 5-bromo-3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine 
• 1290143-11-1 3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)benzonitrile 
• 1377503-46-2 3-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-benzonitrile 
• 1377503-48-4 3-(3-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline 
• 1377503-50-8 3-(5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzonitrile 
• 1377503-55-3 5-(3-methoxyphenyl)-3-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

TRICYCLIC COMPOUNDS AS HPK1 INHIBITOR AND THE USE THEREOF

Disclosed herein is a tricyclic compound of Formula (I), or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions comprising thereof. Also disclosed is a method of treating HPK1 related disorders or diseases by using the compound disclosed herein.

Azaindole derivative myelocyte proliferation inhibitor, preparation method thereof, and application of inhibitor in pharmacy

The invention provides an azaindole derivative myeloid proliferation inhibitor as shown in a formula I. In the formula, R1, R2 and R33 are as defined in the specification. The compound shown in the formula I can be used for remarkably inhibiting the proliferation of myeloid cells represented by MOLM-16, HL-60 and MV-4-11 and related diseases of the myeloid cells. The compound shown in the formula I or the salt thereof or the related pharmaceutical composition provided by the invention has excellent in-vivo and in-vitro inhibitory activity, good druggability and high bioavailability, and does not have obvious injury to visceral organs. Therefore, the compound shown in the formula I or the salt thereof and the related pharmaceutical composition have huge clinical application prospects.

Development of anti-breast cancer PI3K inhibitors based on 7-azaindole derivatives through scaffold hopping: Design, synthesis and in vitro biological evaluation

Breast cancer is the cancer with the highest incidence all over the world. Phosphatidylinositol 3-kinase is an important regulator of intracellular signaling pathways, which is frequently mutated and overexpressed in majority of human breast cancers, and the inhibition of PI3K has been considered as a promising approach for the treatment of the cancer. Here, we report our design and synthesis of new 7-azaindole derivatives as PI3K inhibitors through the scaffold hopping strategy. By varying the groups at the 3-position of 7-azaindole, we identified a series of potent PI3K inhibitors, whose antiproliferative activities against two human breast cancer MCF-7 and MDA-MB-231 cell lines were evaluated. Representative derivatives FD2054 and FD2078 showed better activity than BKM120 in antiproliferation, reduced the levels of phospho-AKT and induced cell apoptosis. All these results suggested that FD2054 and FD2078 are potent PI3K inhibitors that could be considered as potential candidates for the development of anticancer agents.

Discovery of a Novel Series of 7-Azaindole Scaffold Derivatives as PI3K Inhibitors with Potent Activity

The phosphoinositide 3-kinase (PI3K) inhibitors potently inhibit the signaling pathway of PI3K/AKT/mTOR, which provides a promising new approach for the molecularly targeted cancer therapy. In this work, a novel series of 7-azaindole scaffold derivatives was discovered by the fragment-based growing strategy. The structure-activity relationship profiles identified that the 7-azaindole scaffold derivatives exhibit potent activity against PI3K at molecular and cellular levels as well as cell proliferation in a panel of human tumor cells.

COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR

Compounds active on protein kinases are described, as well as methods of making and using such compounds to treat diseases and conditions associated with aberrant activity of protein kinases.

TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF

The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.

PI3K inhibitor, preparation method and application thereof in pharmacy

The invention belongs to the technical field of pharmaceuticals and particularly relates to a PI3K inhibitor, a preparation method and application thereof in the pharmacy. The PI3K inhibitor is a compound of the structure shown by the general formula I or medically acceptable salt of the inhibitor. After the PI3K inhibitor is tested with a PI3K biochemical activity test method, the compound has excellent inhibitory activity to PI3K alpha and PI3K gamma, wherein the IC50 values of a plurality of compounds to the PI3K alpha and PI3K gamma reach nanomole grades (smaller than 100 nM). The result shows that the compounds can provide the inhibitor with better effectiveness and selectivity for curing PI3K-acted proliferative disease, and further a targeted drug for curing No. I type diabetes mellitus, lung disease, breast cancer, prostatic cancer, solid tumor, lymphoma, cardiovascular disease, rheumatoid arthritis, leukemia and the like can be hopefully developed. (Please see the general formula I in the description.).

3,5-Diarylazaindoles as DYRK1A Protein Inhibitors for the Treatment of Cognitive Deficiencies Associated with Down's Syndrome and with Alzheimer's Disease

The present invention relates to a compound of formula (I′) or a pharmaceutically acceptable salt, solvate or hydrate thereof, in which: X3 is F, OH or SH, Y3 is F, OH or SH, X1, X2, X4, X5, Y1, Y2, Y4 and Y5 are, independently of one another, H, F, Cl, Br, OH or SH, and 1 to 2 groups among the X1, X2, X4 and X5 radicals are other than H and/or 1 to 2 groups among the Y1, Y2, Y4 and Y5 radicals are other than H. The present invention also relates to a compound of formula (I′) for use as a medicament, in particular in the prevention and/or treatment of cognitive disorders associated with a dysfunction of the Dyrk1A protein.

Development of DANDYs, new 3,5-diaryl-7-azaindoles demonstrating potent DYRK1A kinase inhibitory activity

A series of 3,5-diaryl-1H-pyrrolo[2,3-b]pyridines were synthesized and evaluated for inhibition of DYRKIA kinase in vitro. Derivatives having hydroxy groups on the aryl moieties (2c, 2j-l) demonstrated high inhibitory potencies with Kis in the low nanomolar range. Their methoxy analogues were up to 100 times less active. Docking studies at the ATP binding site suggested that these compounds bind tightly to this site via a network of multiple H-bonds with the peptide backbone. None of the active compounds were cytotoxic to KB cells at 10-6 M. Kinase profiling revealed that compound 2j showed 2-fold selectivity for DYRK1A with respect to DYRK2 and DYRK3.

1H-Pyrrolo[2,3 b]pyridine derivatives

1H-Pyrrolo[2,3-b]pyridine compounds are inhibitors of cell proliferation/cell vitality and can be employed for the treatment of tumours.