1083326-28-6

Basic information

• Product Name: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
• Synonyms: 3-PhenylsulfonaMidopyridine-5-boronic acid pinacol ester, 96%;N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
• CAS NO: 1083326-28-6
• Molecular Formula: C₁₇H₂₁BN₂O₄S
• Molecular Weight: 360.23564
• Mol File: 1083326-28-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 517.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 7.63±0.40(Predicted)
• CAS DataBase Reference: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide(1083326-28-6)
• EPA Substance Registry System: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide(1083326-28-6)

Safety Data

• Hazardous Substances Data: 1083326-28-6(Hazardous Substances Data)

Usage

General Description

N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide, also known as DBCO-NHS, is a chemical compound commonly used in bioconjugation and labeling applications. It contains a sulfonamide group, which can form stable amide bonds with primary amines in proteins or other biomolecules. The presence of the dioxaborolane group allows for the selective and efficient labeling of molecules with azide groups through copper-free click chemistry. DBCO-NHS is often used in the development of bioorthogonal conjugation strategies and the preparation of biomolecule conjugates for various biological and medical research purposes. It is a versatile and important tool in the field of chemical biology and biochemistry.

Upstream product

• 1192749-74-8 N-(5-bromopyridin-3-yl)-N-(phenylsulfonyl)benzenesulfonamide 
• 98-09-9 benzenesulfonyl chloride 
• 13535-01-8 3-amino-5-bromopyridine 
• 127-08-2 potassium acetate 
• 1084-12-4 N-(5-bromopyridin-3-yl)benzenesulfonamide 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1083325-65-8 N-{5-[3-(2-furanyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide 
• 1083322-56-8 N-{5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide 
• 1083324-04-2 2-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamide 
• 1083324-80-4 N-[5-(3-{4-[2-(methyloxy)phenyl]-1-piperazinyl}-6-quinoxalinyl)-3-pyridinyl]benzenesulfonamide 
• 1083325-49-8 N-(5-{3-[(1-methyl-1H-pyrazol-3-yl)amino]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamide 
• 1083325-51-2 N-{5-[3-(4-{[2-(methylsulfonyl)ethyl]amino}-1-piperidinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide 
• 1083325-72-7 1,1-dimethylethyl 3-oxo-4-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)-1-piperazinecarboxylate 
• 1083325-80-7 N,N-dimethyl-1-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)-4-piperidinesulfonamide 
• 1083325-58-9 3-[(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)amino]benzoic acid 
• 1135310-04-1 N-(5-(4-dimethylaminopyrido[3,2-d]pyrimidin-6-yl)-3-pyridinyl)benzenesulfonamide 
• 1135310-05-2 N-(5-(4-(4-morpholinyl)pyrido[3,2-d]pyrimidin-6-yl)-3-pyridinyl)benzenesulfonamide 
• 1276110-15-6 N-(5-(3-phenylimidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1276110-12-3 N-(5-(3-(2H-tetrazol-5-yl)imidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)-benzenesulfonamide 
• 1276110-04-3 N-(5-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)benzenesulfonamide 

Relevant articles and documents

Prospective evaluation and success of a machine learning hit-to-lead drug development program against phosphatidylinositol 3-kinase α

As a result of the rapidly increasing cost of drug development, efficient methods for early identification of compounds with a high probability of clinical success are needed. Herein, we describe a cheminformatics protocol which dramatically increases quality candidate identification and should reduce the attrition rate of compounds entering the clinic, increasing the cost-effectiveness of drug development. Against the oncology target phosphatidylinositol 3-kinase α, all five compounds synthesized from the protocol were found to have low nanomolar activity. We therefore propose that our protocol can be used as a tool for reducing the synthetic burden required for hit-to-lead optimization.

PHOSPHOTIDYLINOSITOL 3-KINASE INHIBITORS

This disclosure relates to phosphoinositide 3-kinases (PI3Ks) inhibitors such as N-(5-(imidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)sulfonamide derivatives and uses related thereto. In certain embodiments, the disclosure relates to methods of treating PI3K associated diseases or conditions comprising administering an effective amount of a compound disclosed herein to a subject in need thereof. In certain embodiments, the subject is at risk of, exhibiting symptoms of, suffering from, or diagnosed with cancer or a hematological malignancy.

Design and synthesis of imidazopyridine analogues as inhibitors of phosphoinositide 3-kinase signaling and angiogenesis

Phosphatidylinositol 3-kinase α (PI3Kα) is an important regulator of intracellular signaling pathways, controlling remarkably diverse arrays of physiological processes. Because the PI3K pathway is frequently up-regulated in human cancers, the inhibition of PI3Kα can be a promising approach to cancer therapy. In this study, we have designed and synthesized a new series of imidazo[1,2-a]pyridine derivatives as PI3Kα inhibitors through the fragment-growing strategy. By varying groups at the 3- and 6-positions of imidazo[1,2-a]pyridines, we studied the structure-activity relationships (SAR) profiles and identified a series of potent PI3Kα inhibitors. Representative derivatives showed good activity in cellular proliferation and apoptosis assays. Moreover, these inhibitors exhibited noteworthy antiangiogenic activity.