5804-73-9

Usage

Uses

Used in Pharmaceutical Industry:
5-Acetylamino-2-methoxybenzenesulfonyl chloride is used as an intermediate for the production of drugs targeting a range of diseases and conditions. Its reactivity allows for the creation of complex molecular structures that can be tailored to address specific medical needs.
Used as a Coupling Reagent in Peptide Synthesis:
In the field of peptide synthesis, 5-Acetylamino-2-methoxybenzenesulfonyl chloride serves as a coupling reagent, facilitating the linkage of amino acids to form peptides. Its strong reactivity aids in the efficient formation of peptide bonds, which is crucial for the development of bioactive peptides and proteins.
Used as a Protecting Group for Amines in Organic Chemistry:
5-Acetylamino-2-methoxybenzenesulfonyl chloride also functions as a protecting group for amines during organic synthesis. This role is essential in preventing unwanted side reactions, ensuring that the amine group remains intact and available for subsequent reactions, thus maintaining the integrity and functionality of the final product.

InChI:InChI=1/C9H10ClNO4S/c1-6(12)11-7-3-4-8(15-2)9(5-7)16(10,13)14/h3-5H,1-2H3,(H,11,12)

Upstream product

• 51-66-1 4-methoxyacetanilide 
• 104-94-9 4-methoxy-aniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 87670-81-3 (S)-2-(5-Acetylamino-2-methoxy-benzenesulfonylamino)-3-methyl-butyric acid 
• 87670-83-5 (S)-2-(5-Acetylamino-2-methoxy-benzenesulfonylamino)-3-phenyl-propionic acid 
• 729578-90-9 C₁₃H₁₃ClN₂O₃S 
• 87670-82-4 (S)-2-(5-Acetylamino-2-methoxy-benzenesulfonylamino)-4-methyl-pentanoic acid 

Relevant academic research and scientific papers

Novel pyrrole derivatives bearing sulfonamide groups: Synthesis in?vitro cytotoxicity evaluation, molecular docking and DFT study

The synthesis of new derivatives of pyrrole substituted sulfonamide groups is described. The in vitro anticancer activity of these pyrroles was evaluated against MCF7, MOLT-4 and HL-60 cells using MTT assay. The target compounds showed inhibitory activity against tested cell lines. Among the compounds, compound 1a exhibited good cytotoxic activity. The potential of this analog to induce apoptosis was confirmed in a nuclear morphological assay by Hoechst 33258 staining in the PC-12 cells. Finally, molecular docking was performed to determine the probable binding mode of the designed pyrrole derivatives into the active site of FGFR1 protein. DFT calculations were carried out at the B3LYP levels of theory with 6-31+G (d,p) basis set for compound 1a. The point group (C1) of it was obtained based on the optimized structures; the calculation of the FT-IR vibrational frequencies, 1H NMR and 13C NMR chemical shifts of the compound were carried out and compared with those obtained experimentally.

Design, solvent-free synthesis and antibacterial activity evaluation of new coumarin sulfonamides

A simple cost-effective and green method was presented for the synthesis of coumarin bis sulfonamides. Seventeen novel coumarin sulfonamides were synthesized in good to high yield and purity in six steps starting from 2-amino thiazole, aniline, and 4-methoxy aniline. All of the reactions have been done under green conditions without using any hazardous solvent. The chemical structures of the products were elucidated by IR, 1H NMR, and 13C NMR spectroscopy and elemental analysis. Also, the anti-bacterial properties of the synthesized sulfonamides were investigated using two strains of Staphylococcus (gram-positive) and Escherichia coli (gram-negative) bacteria.

Synthesis of some novel sulfonamide-imines as potential antimicrobial agents

Background: Sulfonamide derivatives belong to the most important structural classes of drug molecules. This functional group constitutes the largest class of antibacterial agents. Antibacterial agents with a sulfonamide structure, e.g. sulfadiazine have been therapeutically used for many decades. Approved drugs with a sulfonamide structure have found widespread utility in a number of pharmacology and medicine applications. Literature on sulfonamides highlights the employment of molecular hybridization through conjugation with other pharmacologically interesting scaffolds for the enhancement of medicinal properties. Methods: The synthesis started by the preparation of N-(4-methoxy phenyl) acetamide by the acetylation of p-anisidine with acetic anhydride under solvent-free conditions. Then the product was sulfonated with chlorosulfonic acid. The synthesized sulfonylchloride was reacted with different amines under solvent-free conditions and sulfonamide-amides (3a-j) were obtained in high yield. The products were hydrolysed to the corresponding sulfonamide-amines (4a-j) in acidic conditions. Finally, the amine group was converted to the imine group in ethanol in the presence of acetic acid. The synthesized sulfonamide-amines (4a-j) have been evaluated for their in vitro antibacterial activities against two spp. of Gram positive pathogenic bacteria and 3 spp. of Gram negative bacteria. Results: A series of novel sulfonamide-imines were synthesized starting from p-anisidine with high yields under mild conditions and were screened for in vitro antimicrobial activity against two Grampositive spp. and three Gram-negative spp. The methicillin resistant Staphylococcus aureus (MRSA) showed significant sensitivity against the compounds ((5-((2-chlorobenzylidene)amino)-2-methoxy-N- (2-methoxyphenyl)benzene sulfonamide (5b), N-(4-bromophenyl)-5-((2-chlorobenzylidene)amino)-2- methoxybenzene sulfonamide (5d), 5-((2-chlorobenzylidene)amino)-N-(2-chlorophenyl)-2-methoxybenzene sulfonamide (5g), 5-((2-chlorobenzylidene)amino)-2-methoxy-N-phenethylbenzene sulfonamide (5i) and 5-((2-chlorobenzylidene)amino)-N-cyclohexyl-2-methoxybenzene sulfonamide (5j). Conclusion: In conclusion, we have described a facile, efficient and eco-friendly approach for the preparation of several structurally varied novel sulfonamide-imines in five steps. The reactions are characterized by simple reaction procedures, ease of separation, high yields and purity. Furthermore, the antibacterial activity of the synthesized sulfonamide-imines was evaluated against some Grampositive and Gram-negative microorganism. The methicillin resistant Staphylococcus aureus (MRSA) showed significant sensitivity against some of the synthesized compounds.

A clean synthesis of 2,5-dihydro-1H-pyrrole-2-carboxylates under catalyst-free and solvent-free conditions: cytotoxicity and molecular docking studies

Abstract: A concise, clean synthetic approach to access of 2,5-dihydro-1H-pyrrole-2-carboxylates by two-component condensation reaction of ethyl pyruvate and aniline derivatives under catalyst-free and solvent-free conditions is described. The advantages of this method are practical simplicity, catalyst-free and solvent-free conditions, high atom economy, short reaction times, and good yields of the products. The anticancer potential of synthesized compounds was evaluated against MCF7, MOLT-4 and HL-60 cells by using MTT assay. Among the tested synthesized 2,5-dihydro-1H-pyrrole-2-carboxylates (3a-h, 4a-d), compound 4d having sulfonamide moiety exhibited good cytotoxic activity against all tested cell lines and molecular docking studies also demonstrated that the results of the docking study are in reasonable agreement with cytotoxicity activities. Graphical Abstract: A series of 2,5-dihydro-1H-pyrrole-2-carboxylate derivatives were synthesized by two-component condensation reaction of ethyl pyruvate and aniline derivatives under catalyst-free and solvent-free conditions.[Figure not available: see fulltext.].

Synthesis of new dihydropyrrol-2-one derivatives bearing sulfonamide groups and studies their antibacterial activity

Abstract: A novel series of dihydropyrrol-2-one compounds bearing sulfonamide groups were synthesized and assayed for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Streptococcus epidermidis bacteria. Antibacterial results showed that most of the compounds exhibited the antibacterial activity against P. aeruginosa and S. epidermidis and displayed no inhibition against S. aureus and E. coli. Interestingly, most of the screened compounds were more active than the reference drug trimethoprim-sulfamethoxazole against P. aeruginosa. Among them, one compound exhibited good antibacterial activity in comparison with the reference drugs against P. aeruginosa and may make it as potential an antibacterial agent. Graphical abstract: [Figure not available: see fulltext.].