174208-90-3

Upstream product

• 1179205-40-3 N-(3-(hydroxymethyl)phenyl)-4-methylbenzenesulfonamide 
• 99-61-6 3-nitro-benzaldehyde 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 1709-44-0 m-aminobenzaldehyde 
• 87199-16-4 3-Formylphenylboronic acid 
• 127-65-1 chloroamine-T 
• 1877-77-6 3-aminobenzenemethanol 
• 6952-67-6 2-(3-nitrophenyl)-1,3-dioxolane 
• 6398-87-4 3-aminobenzaldehyde ethylene acetal 

Relevant academic research and scientific papers

Cinnamonitrile adjuvants restore susceptibility to β-lactams against methicillin-resistant staphylococcus aureus

β-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the β-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 μM (E)-3-(5-(3,4-dichlorobenzyl)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg·L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.

Ruthenium-catalyzed enantioselective C-H functionalization: A practical access to optically active indoline derivatives

Ru(II)-catalyzed enantioselective C-H activation/hydroarylation has been developed for the first time, allowing for highly enantioselective synthesis of indoline derivatives via catalytic C-H activation. Commercially available Ru(II) arene complexes and chiral α-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multisubstituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enables access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides

A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates

A novel one-step direct reductive coupling reaction between nitroarenes and sodium arylsulfinates was realized in the presence of an inexpensive Pd/C catalyst. In this procedure, readily available nitroarenes are employed as the nitrogen sources, and sodium arylsulfinates serve as both coupling partners and reductants. The method features high efficiency by using cheap Pd/C with low catalyst loading and good functional group tolerance in the absence of any additional reductants or ligands. This facile and mild synthetic method enables the high efficiency synthesis of functionalized N-arylsulfonamides from readily available substrates.

Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions

Ideally, a sustainable chemical synthesis should involve the use of non-toxic solvents and reactants, easy separations and purification by energy-efficient processes. In this context, reconsidering the synthesis of widely used drugs is especially timely and should allow important benefits to be obtained in terms of environmental impact. Sulfonamides are pertinent as their synthesis generally requires the use of toxic and/or hard-to-remove solvents such as dichloromethane, DMF and DMSO. In addition, toxic and highly reactive sulfur-containing sources such as sulfonyl chloride are often involved and coupled with amines. Moreover, the latter may exhibit some toxicity and are generally difficult to purify. Herein, we disclose the unprecedented and sustainable synthesis of sulfonamides by using sodium sulfinate as a commercial and stable sulfur source and nitroarenes as the nitrogen-containing reactant. In addition, under the optimized conditions only water is used as a “green” solvent and the products are collected by simple filtration.

Structure-activity relationship of the cinnamamide family of antibiotic potentiators for methicillin-resistant: Staphylococcus aureus (MRSA)

Methicillin-resistant Staphylococcus aureus (MRSA) is a global public health threat. MRSA has evolved a complex set of biochemical processes that mobilize the organism for inducible resistance on challenge by β-lactam antibiotics. Interfering pharmacologi

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

Synthesis and biological evaluation of novel synthetic chalcone derivatives as anti-tumor agents targeting Cat L and Cat K

A series of chalcone derivatives bearing benzamide or benzenesulfonamide moieties were synthesized and evaluated for their anti-tumor effect on HCT116, MCF7 and 143B cell lines in vitro. SAR analysis showed that compounds bearing a benzenesulfonamide grou

Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts

New trifunctional organocatalysts with a NHTs Br?nsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions.The cooperativity between the counterion and the NHTs Br?nsted aci