19992-57-5

Basic information

• Product Name: 4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(thiazol-2-yl)benzenesulfonamide
• CAS NO: 19992-57-5
• Molecular Weight: 445.907
• Mol File: 19992-57-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(thiazol-2-yl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(thiazol-2-yl)benzenesulfonamide(19992-57-5)
• EPA Substance Registry System: 4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(thiazol-2-yl)benzenesulfonamide(19992-57-5)

Safety Data

• Hazardous Substances Data: 19992-57-5(Hazardous Substances Data)

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 72-14-0 Sulfathiazole 
• 64-17-5 ethanol 

Relevant articles and documents

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Screening of the NCI Diversity Set-1 identified PI-083 (NSC-45382) a proteasome inhibitor selective for cancer over normal cells. Focused libraries of novel compounds based on PI-083 chloronaphthoquinone and sulfonamide moieties were synthesized to gain a better understanding of the structure-activity relationship responsible for chymotrypsin-like proteasome inhibitory activity. This led to the demonstration that the chloronaphthoquinone and the sulfonamide moieties are critical for inhibitory activity. The pyridyl group in PI-083 can be replaced with other heterocyclic groups without significant loss of activity. Molecular modeling studies were also performed to explore the detailed interactions of PI-083 and its derivatives with the β5 and β6 subunits of the 20S proteasome. The refined model showed an H-bond interaction between the Asp-114 and the sulfonamide moiety of the PI-083 in the β6 subunit.