1576-44-9

Basic information

• Product Name: 4-Nitro-N-phenylbenzenesulfonaMide, 97%
• Synonyms: 4-Nitro-N-phenylbenzenesulfonaMide, 97%
• CAS NO: 1576-44-9
• Molecular Formula: C₁₂H₁₀N₂O₄S
• Molecular Weight: 278.2838
• Mol File: 1576-44-9.mol
• Article Data: 52

Chemical Properties

• Melting Point: 135-136 °C
• Boiling Point: 461.3°Cat760mmHg
• Flash Point: 232.8°C
• Appearance: /
• Density: 1.461g/cm³
• Vapor Pressure: 1.09E-08mmHg at 25°C
• Refractive Index: 1.656
• PKA: 7.31±0.10(Predicted)
• CAS DataBase Reference: 4-Nitro-N-phenylbenzenesulfonaMide, 97%(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-N-phenylbenzenesulfonaMide, 97%(1576-44-9)
• EPA Substance Registry System: 4-Nitro-N-phenylbenzenesulfonaMide, 97%(1576-44-9)

Safety Data

• Hazardous Substances Data: 1576-44-9(Hazardous Substances Data)

Usage

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

Upstream product

• 73901-01-6 p-nitrobenzenesulfonyl azide 
• 71-43-2 benzene 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 98-80-6 phenylboronic acid 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 
• 98-95-3 nitrobenzene 
• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 873-55-2 sodium benzenesulfonate 
• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 62-53-3 aniline 
• 1441409-91-1 (E)-ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 99072-50-1 2-cyano-2-propyl p-nitrobenzenesulfonate 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 59224-71-4 N-Acetyl-4-amino-N-phenyl-benzenesulfonamide 
• 1133046-94-2 N-(2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-5-yl)-4-nitrobenzenesulfonamide 
• 1337919-54-6 (E)-4-nitro-N-phenyl-N-styrylbenzenesulfonamide 
• 1448025-48-6 N-(2-bromoallyl)-4-nitro-N-phenylbenzenesulfonamide 
• 1448025-60-2 N-(3-bromo-2-oxopropyl)-4-nitro-N-phenylbenzenesulfonamide 

Relevant articles and documents

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Discovery of N-(3,4-Dimethylphenyl)-4-(4-isobutyrylphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2- c]quinoline-8-sulfonamide as a Potent Dual MDM2/XIAP Inhibitor

Murine double minute 2 (MDM2) and X-linked inhibitor of apoptosis protein (XIAP) are important cell survival proteins in tumor cells. As a dual MDM2/XIAP inhibitor reported previously, compound MX69 has low potency with an IC50 value of 7.5 μM against an acute lymphoblastic leukemia cell line EU-1. Herein, we report the structural optimization based on the MX69 scaffold, leading to the discovery of a 25-fold more potent analogue 14 (IC50 = 0.3 μM against EU-1). We demonstrate that 14 maintains its mode of action by dual targeting of MDM2 and XIAP through inducing MDM2 protein degradation and inhibiting XIAP mRNA translation, respectively, which resulted in cancer cell growth inhibition and cell death. The results strongly suggest that the scaffold based on 14 is promising for further optimization to develop a new therapeutic agent for leukemia and possibly other cancers where MDM2 and XIAP are dysregulated.

Sulphonamidic Groups as Electron-Withdrawing Units in Ureido-Based Anion Receptors: Enhanced Anion Complexation versus Deprotonation

A sulphonamidic moiety was utilized as an electron-withdrawing group for enhancement of anion complexation features of urea-based receptors. A series of receptors varying in acidity of sulphonamidic and urea NH groups was synthesized and thoroughly tested. The individual complexation properties reflect deprotonation/complexation equilibrium in a given molecule as a function of the substitution. The receptors containing electron-donating groups in conjugation to the sulphonamidic moiety showed higher association constants towards H2PO4? and carboxylate anions, while those containing electron-withdrawing groups inclined to deprotonation of sulphonamidic NH. The deprotonation issue can be avoided by alkylation at the early step of receptor synthesis or it can be utilized for insertion of suitable groups that enable its anchoring on various substrates to form more elaborated receptor structures.