6965-75-9

Basic information

• Product Name: 4-AMINO-N-(4-IODO-PHENYL)-BENZENESULFONAMIDE
• Synonyms: 4-IODOSULFANILANILIDE
• CAS NO: 6965-75-9
• Molecular Formula: C₁₂H₁₁IN₂O₂S
• Molecular Weight: 374.1974
• Mol File: 6965-75-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 497.5 °C at 760 mmHg
• Flash Point: 254.7 °C
• Appearance: /
• Density: 1.844 g/cm³
• Vapor Pressure: 4.93E-10mmHg at 25°C
• Refractive Index: 1.723
• CAS DataBase Reference: 4-AMINO-N-(4-IODO-PHENYL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(4-IODO-PHENYL)-BENZENESULFONAMIDE(6965-75-9)
• EPA Substance Registry System: 4-AMINO-N-(4-IODO-PHENYL)-BENZENESULFONAMIDE(6965-75-9)

Safety Data

• Hazardous Substances Data: 6965-75-9(Hazardous Substances Data)

Usage

General Description

4-AMINO-N-(4-IODO-PHENYL)-BENZENESULFONAMIDE is a chemical compound with the molecular formula C12H11IN2O2S. It is a sulfonamide derivative that contains an amino group and an iodo-phenyl group. This chemical is commonly used in pharmaceutical research and drug development, particularly in the synthesis of potential therapeutic agents. Its structure and properties make it a valuable building block for the creation of new drugs, and it is also used as a chemical intermediate in organic synthesis. Additionally, it exhibits potential biological activity and has been studied for its potential pharmacological effects.

InChI:InChI=1/C12H11IN2O2S/c13-9-1-5-11(6-2-9)15-18(16,17)12-7-3-10(14)4-8-12/h1-8,15H,14H2

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Relevant articles and documents

Design, synthesis, and evaluation of substituted nicotinamide adenine dinucleotide (NAD+) synthetase inhibitors as potential antitubercular agents

Nicotinamide adenine dinucleotide (NAD+) synthetase catalyzes the last step in NAD+ biosynthesis. Depletion of NAD+ is bactericidal for both active and dormant Mycobacterium tuberculosis (Mtb). By inhibiting NAD+ synthetase (NadE) from Mtb, we expect to eliminate NAD+ production which will result in cell death in both growing and nonreplicating Mtb. NadE inhibitors have been investigated against various pathogens, but few have been tested against Mtb. Here, we report on the expansion of a series of urea-sulfonamides, previously reported by Brouillette et al. Guided by docking studies, substituents on a terminal phenyl ring were varied to understand the structure–activity-relationships of substituents on this position. Compounds were tested as inhibitors of both recombinant Mtb NadE and Mtb whole cells. While the parent compound displayed very weak inhibition against Mtb NadE (IC50 = 1000 μM), we observed up to a 10-fold enhancement in potency after optimization. Replacement of the 3,4-dichloro group on the phenyl ring of the parent compound with 4-nitro yielded 4f, the most potent compound of the series with an IC50 value of 90 μM against Mtb NadE. Our modeling results show that these urea-sulfonamides potentially bind to the intramolecular ammonia tunnel, which transports ammonia from the glutaminase domain to the active site of the enzyme. This hypothesis is supported by data showing that, even when treated with potent inhibitors, NadE catalysis is restored when treated with exogenous ammonia. Most of these compounds also inhibited Mtb cell growth with MIC values of 19–100 μg/mL. These results improve our understanding of the SAR of the urea-sulfonamides, their mechanism of binding to the enzyme, and of Mtb NadE as a potential antitubercular drug target.