28860-08-4

Usage

Uses

Used in Pharmaceutical Industry:
N-ethyl-4-nitrobenzenesulfonamide is used as a sulfonamide antimicrobial agent for its ability to inhibit the growth of bacteria and fungi, playing a significant role in the development of medications aimed at treating infections.
Used in Agricultural Industry:
In agriculture, N-ethyl-4-nitrobenzenesulfonamide is used as a preservative and antimicrobial agent to protect crops from microbial spoilage and to extend the shelf life of harvested produce.
Used in Cosmetics and Personal Care Products:
N-ethyl-4-nitrobenzenesulfonamide is utilized as a preservative in cosmetics and personal care products to prevent microbial contamination, ensuring the safety and longevity of these products.
Used in Food Industry:
N-ethyl-4-nitrobenzenesulfonamide is employed as an additive in the food industry to inhibit the growth of bacteria and fungi, thereby preserving the quality and safety of food products.
Used in Water Treatment:
In water treatment processes, N-ethyl-4-nitrobenzenesulfonamide serves as an antimicrobial agent to control microbial growth in water systems, helping to maintain water quality and prevent contamination.
Used in Textile Industry:
N-ethyl-4-nitrobenzenesulfonamide is used in the textile industry as an antimicrobial agent in the production of fabrics, ensuring the longevity and cleanliness of textiles, particularly those used in healthcare and hygiene applications.
Each application of N-ethyl-4-nitrobenzenesulfonamide leverages its antimicrobial properties to enhance the safety, quality, and longevity of products across various industries.

InChI:InChI=1/C8H10N2O4S/c1-2-9-15(13,14)8-5-3-7(4-6-8)10(11)12/h3-6,9H,2H2,1H3

Upstream product

• 75-04-7 ethylamine 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 108-30-5 succinic acid anhydride 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 75-03-6 ethyl iodide 
• 155164-61-7 2-(4-nitrobenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 156840-00-5 2,4-dinitrophenyl 4-nitrobenzenesulfonate 
• 557-66-4 ethanamine hydrochloride 

Downstream Products

• 211675-98-8 N-ethyl-4-nitro-N-phenylbenzenesulfonamide 
• 1709-53-1 4-amino-N-ethylbenzenesulfonamide 
• 1240480-38-9 {(S)-2-ethyl-[(4-nitro-benzenesulfonyl)amino]-1-phenyl-ethyl}carbamic acid tert-butyl ester 
• 1240480-37-8 N-((S)-2-amino-2-phenyl-ethyl)-N-ethyl-4-nitro-benzenesulfonamide 
• 1240480-54-9 4-{(S)-2-[ethyl-(4-nitro-benzenesulfonyl)amino]-1-phenyl-ethylamino}quinazoline-8-carboxylic acid methyl ester 
• 1240480-55-0 4-{(S)-2-[ethyl-(4-nitro-benzenesulfonyl)amino]-1-phenyl-ethylamino}quinazoline-8-carboxylic acid amide 

Relevant academic research and scientific papers

Discovery of 7H-pyrrolo[2,3-d]pyridine derivatives as potent FAK inhibitors: Design, synthesis, biological evaluation and molecular docking study

Focal adhesion kinase (FAK) is an intracellular non-receptor tyrosine kinase responsible for development of various tumor types. Aiming to explore new potent inhibitors, two series of 2,4-disubstituted-7H-pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized on the base of structure-based design strategy. Biological evaluation indicated that most of these new compounds could potently inhibit FAK kinase, leading to the promising inhibitors against the proliferation of U-87MG, A-549, and MDA-MB-231 cancer cell lines. Among them, the optimized compound 18h potently inhibited the enzyme (IC50 = 19.1 nM) and displayed stronger potency than TAE-226 in U-87MG, A-549 and MDA-MB-231 cells, with IC50 values of 0.35, 0.24, and 0.34 μM, respectively. Compound 18h is a multi-target kinase inhibitor. Furthermore, compound 18h also exhibited relatively less cytotoxicity (IC50 = 3.72 μM) toward a normal human cell line, HK2. According to the flow cytometry and wound healing assay results, compound 18h effectively induced apoptosis and G0/G1 phase arrest of MDA-MB-231 cells and suppressed the migration of U-87MG, A-549 and MDA-MB-231 cells. The docking study of compound 18h was performed to elucidate its possible binding modes and to provide a structural basis for the further structural guidance design of FAK inhibitors. Collectively, these data support the further development of compound 18h as a lead compound for FAK-targeted anticancer drug discovery.

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.

Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement

A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods.

Method for preparing chiral amino compound and intermediate thereof

The invention discloses a method for preparing a chiral amino compound and intermediate thereof. The method comprises the step of performing a deprotection reaction as shown in the specification on acompound in a formula D and mercaptide in a solvent, wherein in the compound in the formula D, X is selected from O or NMe; Y is Me when X is O, and Y is H when X is NMe; n is selected from 0, 1, 2, 3, 4 or 5; each R is independently NO2 or CN; the mercaptide is salt formed by thiol and metal, and is shown as RS-M; M is an alkali metal ion, and is especially selected from one or more of Li, Na, K, Ru and Cs; and R is C14-24 alkyl. The preparation method is simple and convenient to operate, has mild reaction conditions, high yield and high product quality, and is applicableto industrial production.

Copper-catalyzed trifluoromethylation and cyclization of aromatic-sulfonyl-group-tethered alkenes for the construction of 1,2-benzothiazinane dioxide type compounds

A multi-talented system: An efficient copper-catalyzed tandem trifluoromethylation/annulation of an electron-deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2-benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.

NOVEL AMINO AZAHETEROCYCLIC CARBOXAMIDES

The invention provides novel substituted amino azaheterocyclic carboxamide compounds according to Formula (I), their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

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.

METHOD OF OBTAINING DERIVATIVES OF 4-(N-ALKYLAMINE)-5,6-DIHYDRO-4H-THIENO-[2,3-B]-THIOPYRAN

The invention is aimed at a compound of formula (I) wherein n is 0, 1 or 2, R1 is a linear or branched alkyl group, R2 is selected from a substituted or non substituted alkyl group, substituted or non substituted aryl group, substitu

Effect of substituent on regioselectivity and reaction mechanism in aminolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates

(Chemical Equation Presented) We report on a kinetic study for the nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzensulfonates (X = 4-MeO, 1a, and X = 4-NO2, 1c) with a series of primary amines in 80 mol % H2O/20 mol % DMSO at 25.0 °C. The reactions proceed through S-O and C-O bond fission pathways competitively. The fraction of the S-O bond fission increases as the attaching amine becomes more basic and the substituent X changes from 4-MeO to 4-NO2, indicating that the regioselectivity is governed by the electronic nature of the substituent X as well as the basicity of amines. The S-O bond fission has been suggested to proceed through an addition intermediate with a change in the rate-determining step (RDS) at pK°a = 8.9 ± 0.1. The electronic nature of the substituent X influences kNS-O and k1 values, but not the k2/k-1 ratios and the pK°a value significantly. Stabilization of the ground state (GS) through resonance interaction between the electron-donating substituent and the electrophilic center has been suggested to be responsible for the decreased reactivity of 1a compared to 1c. The second-order rate constants for the C-O bond fission exhibit no correlation with the electronic nature of the substituent X. The distance effect and the nature of the reaction mechanism have been suggested to be responsible for the absence of the correlation.

Arenesulfonylheterocycles (I): Synthesis and reactions of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with amines

The direct sulfonylation of 4,5-dichloropyridazin-3-ones with some benzenesulfonyl chlorides in the presence of base in tetrahydrofuran gave only the corresponding N-sulfonylated product. The reaction of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with some aliphatic amines under neutral conditions afforded 5-alkylamino-2-benzenesulfonyl-4-chloropyridazin-3-ones and/or the corresponding N-alkyl-benzenesulfonamides.