28045-65-0

Usage

Organic compound

Yes, it contains carbon atoms bonded to hydrogen and other carbon atoms.

Thioether functional group

Yes, it has a sulfur atom bonded to two carbon atoms.

Derived from acetanilide

Yes, it is a modification of the acetanilide molecule.

Common use as a reagent in organic synthesis

Yes, it is used in various chemical reactions to synthesize other compounds.

Applications in the pharmaceutical industry

Yes, it is used in the production of drugs.

Analgesic properties

Yes, it has the ability to relieve pain and is used in the production of pain-relieving drugs.

Potential uses in research and industrial processes

Yes, its unique chemical properties make it useful in a variety of applications.

InChI:InChI=1/C10H11NO2S/c1-7(12)11-9-5-3-4-6-10(9)13-8(2)14/h3-6H,1-2H3,(H,11,12)

Upstream product

• 507-09-5 thioacetic acid 
• 10156-35-1 thiocyanato-acetic acid anilide 
• 4822-44-0 2-mercapto-N-phenylacetamide 
• 108-24-7 acetic anhydride 
• 71-43-2 benzene 
• 587-65-5 N-chloroacetyl-aniline 
• 62-53-3 aniline 
• 10387-40-3 potassium thioacetate 

Downstream Products

• 4822-44-0 2-mercapto-N-phenylacetamide 
• 3095-79-2 N-phenyl-mercaptoacetamide disulfide 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors

Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.

N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB fromPseudomonas aeruginosa

Increasing antimicrobial resistance is evolving to be one of the major threats to public health. To reduce the selection pressure and thus to avoid a fast development of resistance, novel approaches aim to target bacterial virulence instead of growth. Another strategy is to restore the activity of antibiotics already in clinical use. This can be achieved by the inhibition of resistance factors such as metallo-β-lactamases (MBLs). Since MBLs can cleave almost all β-lactam antibiotics, including the “last resort” carbapenems, their inhibition is of utmost importance. Here, we report on the synthesis andin vitroevaluation ofN-aryl mercaptoacetamides as inhibitors of both clinically relevant MBLs and the virulence factor LasB fromPseudomonas aeruginosa. All testedN-aryl mercaptoacetamides showed low micromolar to submicromolar activities on the tested enzymes IMP-7, NDM-1 and VIM-1. The two most promising compounds were further examined in NDM-1 expressingKlebsiella pneumoniaeisolates, where they restored the full activity of imipenem. Together with their LasB-inhibitory activity in the micromolar range, this class of compounds can now serve as a starting point for a multi-target inhibitor approach against both bacterial resistance and virulence, which is unprecedented in antibacterial drug discovery.