20555-67-3

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-N-(3,4-DIMETHYLPHENYL)BENZENESULFONAMIDE is used as a potential therapeutic agent for [specific medical conditions or diseases] due to its ability to inhibit certain enzymes or receptors in the body. Its sulfonamide nature suggests it may have antimicrobial and diuretic properties, which could be harnessed for the treatment of various conditions.
Used in Research and Development:
In the field of medicinal chemistry, 4-AMINO-N-(3,4-DIMETHYLPHENYL)BENZENESULFONAMIDE is used as a chemical probe for studying the mechanisms of action of sulfonamide drugs. Its unique structure provides a basis for the design and synthesis of new compounds with improved pharmacological properties, potentially leading to the discovery of innovative medications.

InChI:InChI=1/C14H16N2O2S/c1-10-3-6-13(9-11(10)2)16-19(17,18)14-7-4-12(15)5-8-14/h3-9,16H,15H2,1-2H3

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 95-64-7 4-amino-o-xylene 
• 16937-24-9 N-(3,4-dimethylphenyl)-4-nitrobenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 2158-17-0 N-(4-(N-(3,4-dimethylphenyl)sulfamoyl)phenyl)acetamide 

Downstream Products

• 1160212-29-2 C₂₁H₂₀N₂O₆S 

Relevant academic research and scientific papers

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.

QUINOLINE DERIVATIVES AND USES IN MANAGING CANCER

Provided herein are compounds, pharmaceutical compositions including such compounds, and methods of using such compounds to treat diseases or disorders associated with MDM2 activity.

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.

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.

Synthesis of n-mono-and n,n-disubstituted 4-aminobenzenesulfonamides

-N-Mono-and N,N-disubstituted 4-aminobenzenesulfonamides were synthesized by reaction of 4-acetylacetylaminobenzenesulfonyl chloride with the corresponding primary and secondary aliphatic and aromatic amines, followed by removal of the acetyl group via acid hydrolysis.