80-37-5

Basic information

• Product Name: N-(m-nitrophenyl)benzenesulphonamide
• Synonyms: N-(m-nitrophenyl)benzenesulphonamide
• CAS NO: 80-37-5
• Molecular Formula: C₁₂H₁₀N₂O₄S
• Molecular Weight: 278.2838
• EINECS: 201-273-0
• Mol File: 80-37-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 443.2°C at 760 mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.461g/cm³
• Vapor Pressure: 4.72E-08mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: N-(m-nitrophenyl)benzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(m-nitrophenyl)benzenesulphonamide(80-37-5)
• EPA Substance Registry System: N-(m-nitrophenyl)benzenesulphonamide(80-37-5)

Safety Data

• Hazardous Substances Data: 80-37-5(Hazardous Substances Data)

Usage

General Description

N-(m-nitrophenyl)benzenesulphonamide, also known as N-(3-nitrophenyl)benzenesulfonamide, is an organic compound with the chemical formula C12H10N2O4S. It is a sulfonamide derivative and is commonly used as a reagent for testing the presence of primary amines in organic compounds. N-(m-nitrophenyl)benzenesulphonamide is a white to yellow crystalline powder that is sparingly soluble in water but more soluble in organic solvents such as ethanol and acetone. N-(m-nitrophenyl)benzenesulphonamide has applications in the pharmaceutical and chemical industries, particularly in the synthesis of various organic compounds. Additionally, it is used as an intermediate in the manufacturing of dyes, pigments, and other organic derivatives.

InChI:InChI=1/C12H10N2O4S/c15-14(16)11-6-4-5-10(9-11)13-19(17,18)12-7-2-1-3-8-12/h1-9,13H

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 99-09-2 3-nitro-aniline 
• 512-35-6 benzenesulfonic anhydride 
• 72399-82-7 1-Benzenesulfonyl-4-dimethylamino-pyridinium; chloride 
• 72385-26-3 1-Benzenesulfonyl-4-dimethylamino-pyridinium; bromide 
• 72385-28-5 N-phenylsulfonyl-4-dimethylaminopyridinium benzenesulfonate 
• 2297-65-6 benzenesulfonyl bromide 
• 108-98-5 thiophenol 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 104997-09-3 N-(3-aminophenyl)benzenesulfonamide 
• 108368-77-0 benzenesulfonic acid-[N-(2-hydroxy-ethyl)-3-nitro-anilide] 
• 313670-14-3 benzenesulfonic acid-(N-methyl-3-nitro-anilide) 
• 117309-44-1 [Benzenesulfonyl-(3-nitro-phenyl)-amino]-acetic acid 
• 80650-44-8 3-benzenesulfonylamino-benzenediazonium; chloride 
• 189340-23-6 N-Benzyl-N-(3-nitrophenyl)benzenesulfonamide 

Relevant articles and documents

Probing 2H-Indazoles as Templates for SGK1, Tie2, and SRC Kinase Inhibitors

The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2-substituted aza-2H-indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so-far underrepresented aza-2H-indazole scaffold, indazoles were connected at the N2 position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza-2H-indazole derivatives showed good initial selective inhibition against SGK1, Tie2, and SRC kinases, with the best representatives having IC50 values in the range of 500 nm. In a comparative computational study, these data were analyzed and rationalized in light of docking studies.

BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BDR4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BDR4 are also disclosed. In certain aspects, disclosed are compounds of Formula I through IV.

Potent Pan-Raf and Receptor Tyrosine Kinase Inhibitors Based on a Cyclopropyl Formamide Fragment Overcome Resistance

While selective BRafV600E inhibitors have been proven effective clinically, acquired resistance rapidly develops through reactivation of the mitogen-activated protein kinase (MAPK) pathway. Simultaneous targeting of multiple nodes in the pathway offers the prospect of enhanced efficacy as well as reduced potential for acquired resistance. Replacement pyridine group of Y-1 by a cyclopropyl formamide group afforded I-01 as a novel multitargeted kinase inhibitor template. I-01 displayed enzyme potency against Pan-Raf and receptor tyrosine kinases (RTKs). Based on the binding mode of I-01, analogues I-02-I-18 were designed and synthesized. The most promising compound I-16 potently inhibits all subtypes of Rafs with IC50 values of 3.49 (BRafV600E), 8.86 (ARaf), 5.78 (BRafWT), and 1.65 nM (CRaf), respectively. I-16 not only exhibit comparable antiproliferative activities with positive control compounds against HepG2, SW579, MV4-11, and COLO205 cell lines, but also suppress the proliferation of melanoma SK-MEL-2 harboring overexpressed BRafWT with IC50 values of 0.93 μM. The Western blot results for the ERK inhibition in human melanoma SK-MEL-2 cell lines show that I-16 inhibits the proliferation of SK-MEL-2 cell lines without paradoxical activation of ERK, which support the hypothesis that the inhibition of Pan-Raf and RTKs might be a tractable strategy to overcome the resistance of melanoma induced by the therapy with the current selective BRafV600E inhibitors.