16803-96-6

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 95-53-4 o-toluidine 
• 109847-18-9 4-nitro-N-(2-tolyl)benzenesulfonamide 
• 19838-02-9 N-acetyl-sulfanilic acid o-toluidide 

Downstream Products

• 111456-12-3 coumarin-3N-(4'-(N'-o-methylphenyl)sulphonamidophenyl)carboxamide 
• 1262334-00-8 2-[(2,6-dichlorophenyl)amino]-N₁-(2-methylphenyl)-N₄-phenylacetoxyacetamidobenzenesulfonamide 
• 1258977-85-3 6-chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(2-methylphenylsulfamoyl)phenyl]amide 
• 1258977-97-7 6-hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(2-methylphenylsulfamoyl)phenyl]amide 
• 114854-08-9 1,3-dihydro-5-1-(o-tolyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-(p-tolyl)-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 114853-94-0 1,3-dihydro-5-1-(o-tolyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-phenyl-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 1160212-17-8 C₂₀H₁₈N₂O₆S 
• 1383607-69-9 4-(3-ethylureido) N-2-tolylbenzenesulfonamide 
• 1383607-52-0 4-[3-(3-chloropropyl)ureido]-N-(2-tolyl)benzenesulfonamide 
• 1383607-36-0 4-[3-(2-chloroethyl)ureido] N-2-tolylbenzenesulfonamide 
• 1204290-61-8 4-(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-N-o-tolyl-benzenesulfonamide 
• 1160212-33-8 C₂₆H₂₄N₂O₉S 
• 111456-08-7 coumarin-3N-(4'-(N'-p-bromo-o-methylphenyl)sulphonamidophenyl)carboxamide 

Relevant academic research and scientific papers

Structure-activity relationships of agonists for the orphan G protein-coupled receptor GPR27

GPR27 belongs, with GPR85 and GPR173, to a small subfamily of three receptors called “Super-Conserved Receptors Expressed in the Brain” (SREB). It has been postulated to participate in key physiological processes such as neuronal plasticity, energy metabolism, and pancreatic β-cell insulin secretion and regulation. Recently, we reported the first selective GPR27 agonist, 2,4-dichloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (I, pEC50 6.34, Emax 100%). Here, we describe the synthesis and structure-activity relationships of a series of new derivatives and analogs of I. All products were evaluated for their ability to activate GPR27 in an arrestin recruitment assay. As a result, agonists were identified with a broad range of efficacies including partial and full agonists, showing higher efficacies than the lead compound I. The most potent agonist was 4-chloro-2,5-difluoro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7y, pEC50 6.85, Emax 37%), and the agonists with higher efficacies were 4-chloro-2-methyl-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7p, pEC50 6.04, Emax 123%), and 2-bromo-4-chloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7r, pEC50 5.99, Emax 123%). Docking studies predicted the putative binding site and interactions of agonist 7p with GPR27. Selected potent agonists were found to be soluble and devoid of cellular toxicity within the range of their pharmacological activity. Therefore, they represent important new tools to further characterize the (patho)physiological roles of GPR27.

Nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity

Four series of forty-five nitrogen-containing polyhydroxylated aromatics based on caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase (IN) inhibitors. Most of these compounds inhibited IN catalytic activities in low micromolar range. Among these new analogues, compounds 9e and 9f were the most potent IN inhibitors with IC50 value of 0.7 μM against strand transfer reaction. Their key structure-activity relationships were also discussed.

Synthesis, biological evaluation, and structure-activity relationships of novel substituted N-phenyl ureidobenzenesulfonate derivatives blocking cell cycle progression in s-phase and inducing DNA double-strand breaks

Twenty-eight new substituted N-phenyl ureidobenzenesulfonate (PUB-SO) and 18 N-phenylureidobenzenesulfonamide (PUB-SA) derivatives were prepared. Several PUB-SOs exhibited antiproliferative activity at the micromolar level against the HT-29, M21, and MCF-

ALKYLUREA DERIVATIVES ACTIVE AGAINST CANCER CELLS

Compounds of formula (I) : wherein A, m, n, R1, X, Y, R2, R3, R4, R5 and R6, as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.

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.

Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester

A series of nitrogen-containing polyhydroxylated aromatics from caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase inhibitors. Most of these compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in the 3′-end processing and the strand transfer. Their key structure-activity relationship was also discussed.

Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance.