6298-15-3

Basic information

• Product Name: 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide
• CAS NO: 6298-15-3
• Molecular Formula: C₂₁H₁₄ClN₃O₄S
• Molecular Weight: 439.8716
• Mol File: 6298-15-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 615.9°C at 760 mmHg
• Flash Point: 326.3°C
• Density: 1.56g/cm³
• Vapor Pressure: 4.21E-15mmHg at 25°C
• Refractive Index: 1.721
• CAS DataBase Reference: 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide(6298-15-3)
• EPA Substance Registry System: 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide(6298-15-3)

Safety Data

• Hazardous Substances Data: 6298-15-3(Hazardous Substances Data)

Usage

General Description

4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide, also known as N-(2-pyridyl)-4-(2,3-dihydro-1,4-naphthoquinonyl)aniline-5-sulfonamide, is a chemical compound with the molecular formula C21H16ClN3O5S. It is a sulfonamide derivative with potential antineoplastic activity, meaning it has the ability to inhibit or prevent the growth and spread of tumors. 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]-N-(pyridin-2-yl)benzenesulfonamide targets and binds to carbonic anhydrase IX (CA-IX), an enzyme that is overexpressed in hypoxic (oxygen-deprived) cancer cells, thereby inhibiting its activity and resulting in the disruption of tumor cell pH regulation and growth. This chemical compound is of interest in the development of new cancer treatments and may have potential applications in cancer therapy.

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 144-83-2 sulphapyridine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 103-84-4 Acetanilid 
• 19077-98-6 N-acetylsulfapyridine 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 1204290-41-4 4-(3-morpholino-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)benzenesulfonamide 
• 1204290-40-3 4-(3-(4-methylpiperazin-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)-benzenesulfonamide 
• 1241891-89-3 C₂₃H₁₈ClN₃O₄S 
• 1204290-38-9 4-(3-(dimethylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)-benzenesulfonamide 
• 1204290-39-0 4-(3-(benzyl(methyl)amino)-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)-benzenesulfonamide 
• 1241891-88-2 C₂₂H₁₆ClN₃O₄S 
• 1241891-93-9 C₂₉H₂₂ClN₃O₄S 
• 1241891-91-7 C₂₈H₁₉ClN₄O₆S 
• 1241891-94-0 C₂₉H₁₉ClF₃N₃O₄S 
• 1241891-90-6 C₂₈H₂₀ClN₃O₄S 
• 1241891-92-8 C₃₂H₂₂ClN₃O₄S 

Relevant articles and documents

Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors

A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.

Preparation of some sulfonamide and diaminodiphenyl sulfone analogs of 1,4-naphthoquinone.

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