1083326-17-3

Basic information

• Product Name: N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide
• Synonyms: N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide
• CAS NO: 1083326-17-3
• Molecular Formula: C₁₁H₈BrClN₂O₂S
• Molecular Weight: 347.61542
• Mol File: 1083326-17-3.mol

Chemical Properties

• Boiling Point: 449.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.738±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 6.02±0.40(Predicted)
• CAS DataBase Reference: N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide(1083326-17-3)
• EPA Substance Registry System: N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide(1083326-17-3)

Safety Data

• Hazardous Substances Data: 1083326-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Research:
In the agrochemical industry, N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide is utilized as a starting material for the synthesis of various agrochemicals, including pesticides and herbicides. Its potential biological activities, such as antiviral, antibacterial, and antifungal properties, make it a promising candidate for the development of novel agrochemicals to combat pests and diseases in agriculture.
Used in Organic Synthesis:
N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide is employed as a versatile reagent in organic synthesis. Its reactive functional groups and heterocyclic ring system allow for various chemical transformations, enabling the production of a wide range of organic compounds with diverse applications in different industries.
Used in Antiviral Applications:
N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide has demonstrated antiviral properties, making it a potential candidate for the development of antiviral drugs. Its ability to inhibit viral replication and reduce viral load can be harnessed to develop new therapeutic agents for the treatment of viral infections.
Used in Antibacterial Applications:
N-(5-broMo-2-chloropyridin-3-yl)benzenesulfonaMide's antibacterial properties make it a promising candidate for the development of new antibiotics. Its potential to target and inhibit the growth of bacteria can be utilized in the creation of novel antimicrobial agents to combat bacterial infections and drug-resistant strains.
Used in Antifungal Applications:
N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide's antifungal properties have been recognized, and it can be employed in the development of new antifungal drugs. Its ability to inhibit fungal growth and treat fungal infections can be leveraged to create effective therapeutic agents for the management of various fungal diseases.

Upstream product

• 588729-99-1 3-amino-5-bromo-2-chloropyridine 
• 98-09-9 benzenesulfonyl chloride 
• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 914358-73-9 5-bromo-2-methylpyridin-3-ylamine 

Downstream Products

• 1148008-50-7 N-{2-chloro-5-[3-oxo-4-(phenylmethyl)-3,4-dihydro-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide 
• 1148008-70-1 N-{2-chloro-5-[4-(4-pyridinyl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-pyridinyl}benzenesulfonamide 
• 1148008-47-2 N-{2-chloro-5-[3-oxo-4-(phenylmethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-pyridinyl}benzenesulfonamide 
• 1148008-49-4 N-{2-chloro-5-[4-(phenylmethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-pyridinyl}benzenesulfonamide 

Relevant articles and documents

Bioisosteric replacements of the indole moiety for the development of a potent and selective PI3Kδ inhibitor: Design, synthesis and biological evaluation

Based on indole scaffold, a potent and selective phosphoinositide 3-kinase delta (PI3Kδ) inhibitor, namely FD223, was developed by the bioisosteric replacement drug discovery approach and studied for the treatment of acute myeloid leukemia (AML). In vitro

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 cinnoline derivatives as potent PI3K inhibitors with antiproliferative activity

Cinnoline is a potential pharmacophore which has rarely been reported for uses as PI3K inhibitors. In this study, a series of cinnoline derivatives were developed as PI3K inhibitors and evaluated for enzymatic and cellular activities. Most compounds displ

Cnoline compound PI3K kinase inhibitor as well as preparation method and application thereof in pharmacy

The invention provides a cinnoline compound PI3K kinase inhibitor as shown in a formula I. In the cinnoline compound PI3K kinase inhibitor, and R1, R2 and R3 are defined in the specification. The invention also provides a pharmaceutical composition of the

Discovery of 6′-chloro-N-methyl-5’-(phenylsulfonamido)-[3,3′-bipyridine]-5-carboxamide (CHMFL-PI4K-127) as a novel Plasmodium falciparum PI(4)K inhibitor with potent antimalarial activity against both blood and liver stages of Plasmodium

Starting from a bipyridine-sulfonamide scaffold, medicinal chemistry optimization leads to the discovery of a novel Plasmodium falciparum PI4K kinase (PfPI4K) inhibitor compound 15g (CHMFL-PI4K-127, IC50: 0.9 nM), which exhibits potent activity against 3D7 Plasmodium falciparum (P. falciparum) (EC50: 25.1 nM). CHMFL-PI4K-127 displays high selectivity against PfPI4K over human lipid and protein kinase. In addition, it exhibits EC50 values of 23–47 nM against a panel of the drug-resistant strains of P. falciparum. In vivo, the inhibitor demonstrates the favorable pharmacokinetic properties in both rats and mice. Furthermore, oral administration of CHMFL-PI4K-127 exhibits the antimalaria efficacy in both blood stage (80 mg/kg) and liver stage (1 mg/kg) of Plasmodium in infected rodent model. The results suggest that CHMFL-PI4K-127 might be a new potential drug candidate for malaria.

DUAL ATM AND DNA-PK INHIBITORS FOR USE IN ANTI-TUMOR THERAPY

Provided herein are compounds of the Formula (I), (II), and (III), as well as pharmaceutically acceptable salts thereof, wherein the substituents are those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of oncologic diseases.

Micro-reactor tandem synthesis method of indole anticancer drug molecules

The invention relates to a micro-reactor tandem synthesis method of indole anticancer drug molecules. The method comprises the following steps: a reaction liquid 1 and a reaction liquid 2 are mixed, then are introduced into a first micro-reactor, and are reacted to obtain a first effluent, the first effluent and a reaction liquid 3 are mixed, then are introduced into a second micro-reactor, and are reacted to obtain a second effluent, the second effluent and a reaction liquid 4 are mixed, then are introduced into a third micro-reactor, and are reacted to obtain a final effluent, and the finaleffluent is concentrated and separated to obtain the indole anticancer drug molecules, wherein the reaction liquid 1 is a mixed solution containing 5-bromine-3-amino-2-substituted (R1)-pyridine, the reaction liquid 2 is substituted (R2)-benzenesulfonyl chloride, the reaction liquid 3 is a mixed solution containing bis(pinacolato)diboron, the reaction liquid 4 is a mixed solution containing a 5-bromo-7-azaindole derivative, and the indole anticancer drug molecules are benzenesulfonamidopyridylazaindole compounds. Compared with the prior art, the method of the invention has the advantages of high reaction efficiency, few side reactions and simple production process.

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.

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.).

Optimization of Novel Indazoles as Highly Potent and Selective Inhibitors of Phosphoinositide 3-Kinase δ for the Treatment of Respiratory Disease

Optimization of lead compound 1, through extensive use of structure-based design and a focus on PI3Kδ potency, isoform selectivity, and inhaled PK properties, led to the discovery of clinical candidates 2 (GSK2269557) and 3 (GSK2292767) for the treatment of respiratory indications via inhalation. Compounds 2 and 3 are both highly selective for PI3Kδ over the closely related isoforms and are active in a disease relevant brown Norway rat acute OVA model of Th2-driven lung inflammation.